Featured in a Home & Garden TV Special 30 South Mountain Road
About this house rental
Situated in Pittsfield, this lovely house for $308 per night is a fantastic choice for your next break. Comfortable, quiet home in Pittsfield minutes from Tanglewood, Berkshire Theater Festivals and other year round attractions. Oldest one room school house in New England and listed as a U.S. National Historic Place. Built in 1825 and rebuilt 1843 after a fire. Morewood has been used continually by the community until being converted to a private residence in 1985. The home was completely renovated in 2010 with glass and tile bathroom and updates throughout the 1000 square foot interior located in the middle of an acre wooded lot on a quiet mountain road. The bedroom with a queen sized bed is on the ground floor next to the bathroom with a closet and electric heater. The ground floor has the bathroom, a fully equipped kitchen, the original blackboard, very large windows, a great room with dining table for eight, gas ceramic stove, sofa and TV/DVD and bedroom for two. The sofa can be converted to a queen size bed for guests or kids or to sleep in front the fireplace in the winter. The bedroom in the loft above the great room has twin beds, a Roku TV, closet and AC window unit. The wooded lot is fenced in for pet safety with a pond and running brook on two sides. The stone patio has a dining table and chairs for four, charcoal grill, Adirondack chairs and hammock under the trees near the fire pit. For background on the Berkshires watch the HGTV video on this website about the history of Morewood School and also the Prime Video "Melville in Love" with many scenes of the Morewood estate and Herman Melville's nearby home where he wrote the great American novel "Moby Dick". Keywords: house, berkshire, pet, friendly, schoolhouse, historic
Amenities
Air conditioner
Pets allowed
Kitchen / Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony / Patio
Dishwasher
TV
Garden
Map of Pittsfield, MA
Reviews
4.8/5.0
Outstanding(79 Reviews)
5.0
We have stayed here many times. The schoolhouse , property with fenced yard and location are perfect for us and our dog. Bob is a wonderful host. Having the first floor bedroom, which is new since our last visit, is an asset.
5.0
We had a great stay at this former schoolhouse. Couldn’t have been more charming!
4.0
It was relaxing. The weather was not the best. However, my dog and I enjoyed local trails and shopping.
5.0
My wife attended 1st, 2ed, & 3rd grade at the Morewood schoolhouse back in the late 40s. It brought back so many memories for her.
5.0
Our family was scattered for Thanksgiving this year, and our kitchen was damaged in a mishap caused by our upstairs neighbors, so we decided to escape to the Berkshires for a quiet and peaceful holiday. The lovely, big kitchen was a particular draw for us--very well stocked with quality appliances, pots and pans, and everything you might need. There's a great wine store just down the street (Spirited) and a lovely market (Guido's) as well. And while we were content on this trip to just hang out at the house, there is so much to do just a short drive away.
5.0
Our family was scattered for Thanksgiving this year, and our kitchen was damaged in a mishap caused by our upstairs neighbors, so we decided to escape to the Berkshires for a quiet and peaceful holiday. The lovely, big kitchen was a particular draw for us--very well stocked with quality appliances, pots and pans, and everything you might need. There's a great wine store just down the street (Spirited) and a lovely market (Guido's) as well. And while we were content on this trip to just hang out at the house, there is so much to do just a short drive away.
5.0
From the very beginning, this was the perferct property to VRBO. I had to change my booking dates and Mr. Clydesdale was very helpful. The property was impecable; the kitchen was fully stocked, the decor was so quaint and charming, the beds and linens were clean and comfortable. We were also able to enjoy the outdoor seating area around the fire pit each night and listen to the brook babble in the background. There is also a swingset out front to enjoy. The property is a very quick, safe and easy 20-30 min walk to the center of Pittsfield. We will be back to this amazing property!!
5.0
From the very beginning, this was the perferct property to VRBO. I had to change my booking dates and Mr. Clydesdale was very helpful. The property was impecable; the kitchen was fully stocked, the decor was so quaint and charming, the beds and linens were clean and comfortable. We were also able to enjoy the outdoor seating area around the fire pit each night and listen to the brook babble in the background. There is also a swingset out front to enjoy. The property is a very quick, safe and easy 20-30 min walk to the center of Pittsfield. We will be back to this amazing property!!
5.0
My wife and I stayed at the Morewood School for 3 nights on a Berkshires trip to celebrate our 20th anniversary. The house is fantastic! Perfectly set up with everything you need for a wonderful stay. The location is great as it’s midway between Great Barrington and North Adams, with plenty in between. An absolutely perfect weekend. If you’re looking to book the Morewood for a stay, DO IT. Don’t hesitate. The pictures on the listing are great, but don’t do it justice, as it’s such a great spot.
5.0
This was perfect! My husband and I took a 4 day trip to celebrate my 65th birthday and went to concerts at Tanglewood ! The little red school house is so close it made for easy coming and goings. The inside of the house is just pristine and so comfortable. My only comment - it would be nice if a broom could be taken to the outside of the property and perhaps a bit of clean up outside. When my husband and I drove up, due to the condition of the outside, we weren't sure what we'd find in the inside. Happily all was wonderful.
Thanks for the experience. Lisa U.
5.0
Well located to get to all the things we wanted to do.
5.0
My wife and I stayed at the Morewood School for 3 nights on a Berkshires trip to celebrate our 20th anniversary. The house is fantastic! Perfectly set up with everything you need for a wonderful stay. The location is great as it’s midway between Great Barrington and North Adams, with plenty in between. An absolutely perfect weekend. If you’re looking to book the Morewood for a stay, DO IT. Don’t hesitate. The pictures on the listing are great, but don’t do it justice, as it’s such a great spot.
5.0
Well located to get to all the things we wanted to do.
5.0
Great location. Comfortable, clean and well stocked. Absolutely charming home and property.
Looking forward to coming back.
5.0
Great location. Comfortable, clean and well stocked. Absolutely charming home and property.
Looking forward to coming back.
4.0
What a lovely time we had at the little red schoolhouse! The inside was very clean and nicely updated. The lovely kitchen was spacious and we certainly enjoyed cooking during our stay. It was a little warm inside, even with the AC unit upstairs running full blast! However, we were there during the hottest part of the year and it was very warm outside, so that is to be expected. The only reason why I did not give five stars was because the front and back entrances were full of bugs and cobwebs as well as the previous renters left their trash and an animal got into it and we promptly picked it up. We certainly enjoyed having our dog with us. However, we were not able to keep him outside without being hooked up to a leash. This was due to several areas of the fence that had big gaps or holes where even a big dog could get through. However, this was easily managed. The location was great, especially for going to Lenox, Stockbridge, and some of the surrounding attractions. Guido’s was a must for food shopping! I would definitely stay at the little red schoolhouse again.
5.0
This was perfect! My husband and I took a 4 day trip to celebrate my 65th birthday and went to concerts at Tanglewood ! The little red school house is so close it made for easy coming and goings. The inside of the house is just pristine and so comfortable. My only comment - it would be nice if a broom could be taken to the outside of the property and perhaps a bit of clean up outside. When my husband and I drove up, due to the condition of the outside, we weren't sure what we'd find in the inside. Happily all was wonderful.
Thanks for the experience. Lisa U.
5.0
It was very fun to stay in this historic property. The renovations are stunning, especially the kitchen. I enjoyed how they melded the old and the new to keep the integrity of the old school house. I had my Golden Retriever with me and the grounds were amazing for him to be able to chase a stick down to the creek. However, it is quite muddy when there has been a lot of rain! The loft bedroom was quite comfortable and fortunately there were fans and there is no AC. The house was beautifully appointed and we thoroughly enjoyed both the indoor and outdoor spaces!
4.0
What a lovely time we had at the little red schoolhouse! The inside was very clean and nicely updated. The lovely kitchen was spacious and we certainly enjoyed cooking during our stay. It was a little warm inside, even with the AC unit upstairs running full blast! However, we were there during the hottest part of the year and it was very warm outside, so that is to be expected. The only reason why I did not give five stars was because the front and back entrances were full of bugs and cobwebs as well as the previous renters left their trash and an animal got into it and we promptly picked it up. We certainly enjoyed having our dog with us. However, we were not able to keep him outside without being hooked up to a leash. This was due to several areas of the fence that had big gaps or holes where even a big dog could get through. However, this was easily managed. The location was great, especially for going to Lenox, Stockbridge, and some of the surrounding attractions. Guido’s was a must for food shopping! I would definitely stay at the little red schoolhouse again.
5.0
We stayed here for a few nights while our house was under renovation. It offered everything we needed. The inside was very clean and comfortable. The kitchen was large and had plenty of cookware available. The outside fenced area was a good backup for leash walking our dogs, but I wouldn't recommend it for someone expecting to be able to off-leash their dog as some sections of the fence have been pulled down pretty low and need repair. We did find countless hiking trails nearby, so this was a great spot to be if you love hiking! Would definitely recommend this spot to friends and family.
5.0
It was very fun to stay in this historic property. The renovations are stunning, especially the kitchen. I enjoyed how they melded the old and the new to keep the integrity of the old school house. I had my Golden Retriever with me and the grounds were amazing for him to be able to chase a stick down to the creek. However, it is quite muddy when there has been a lot of rain! The loft bedroom was quite comfortable and fortunately there were fans and there is no AC. The house was beautifully appointed and we thoroughly enjoyed both the indoor and outdoor spaces!
5.0
Cute Historic property
We stayed here for a few nights while our house was under renovation. It offered everything we needed. The inside was very clean and comfortable. The kitchen was large and had plenty of cookware available. The outside fenced area was a good backup for leash walking our dogs, but I wouldn't recommend it for someone expecting to be able to off-leash their dog as some sections of the fence have been pulled down pretty low and need repair. We did find countless hiking trails nearby, so this was a great spot to be if you love hiking! Would definitely recommend this spot to friends and family.
5.0
We were very pleased with everything about the Moorewood little red schoolhouse..wonderful spot for 2 from which to explore the Berkshire hills and towns! The open floor plan and perfectly equipped kitchen were enjoyed to the fullest. And it suited us epecially well with our pittie, who loved the freedom of the fenced yard. Thank you for a wonderful stay at your comfortable and lovingly restored historic home in western MA!
5.0
This vrbo is even nicer than the listing. Kitchen is newly renovated. The house is fully stocked and incredibly clean. Only minutes from Lenox. Perfect long weekend for my husband and me, along with our puppy (who loved the yard).
Only suggestion to the owners: please remove the winter window covers and add screens so we can open the windows next time.
5.0
Welcome Get-away
We were very pleased with everything about the Moorewood little red schoolhouse..wonderful spot for 2 from which to explore the Berkshire hills and towns! The open floor plan and perfectly equipped kitchen were enjoyed to the fullest. And it suited us epecially well with our pittie, who loved the freedom of the fenced yard. Thank you for a wonderful stay at your comfortable and lovingly restored historic home in western MA!
4.0
The house is well appointed. It gets 4 stars instead of 5 for just a couple of things:
The kitchen is the most well stocked/appointed kitchen I have ever stayed in. The drawback is that was very little room for our things/food. There is a cupboard filled with china that is locked. That cupboard would be better used for guests.
Be alerted that the hot water tank really only allows for a shower and a half before the water starts getting chilly.
The house needs a little TLC on the outside but the interior is excellent. The AC in the bedroom is super efficient.
The surrounding area was filled with fun things to do and it was so nice to come home to this schoolhouse.
We would definitely stay there again.
4.0
Lovely and well appointed.
The house is well appointed. It gets 4 stars instead of 5 for just a couple of things:
The kitchen is the most well stocked/appointed kitchen I have ever stayed in. The drawback is that was very little room for our things/food. There is a cupboard filled with china that is locked. That cupboard would be better used for guests.
Be alerted that the hot water tank really only allows for a shower and a half before the water starts getting chilly.
The house needs a little TLC on the outside but the interior is excellent. The AC in the bedroom is super efficient.
The surrounding area was filled with fun things to do and it was so nice to come home to this schoolhouse.
We would definitely stay there again.
5.0
Exceptional weekend
This vrbo is even nicer than the listing. Kitchen is newly renovated. The house is fully stocked and incredibly clean. Only minutes from Lenox. Perfect long weekend for my husband and me, along with our puppy (who loved the yard).
Only suggestion to the owners: please remove the winter window covers and add screens so we can open the windows next time.
5.0
This is our third time staying at the Morewood Schoolhouse and it felt like coming home. Perfect size for a comfortable long weekend (or longer, for that matter!), every necessity we could think of. Allowed us to enjoy our weekend events with room for lazy breakfasts and late dinners of our own making. Cozy in the chilly , rainy temps of the first part of the weekend, cool and comfortable when the temperatures rose. The babbling brook, the touch of history, the location close enough to everything we would need . . .wish we could have stayed longer!
5.0
Always a pleasure!
This is our third time staying at the Morewood Schoolhouse and it felt like coming home. Perfect size for a comfortable long weekend (or longer, for that matter!), every necessity we could think of. Allowed us to enjoy our weekend events with room for lazy breakfasts and late dinners of our own making. Cozy in the chilly , rainy temps of the first part of the weekend, cool and comfortable when the temperatures rose. The babbling brook, the touch of history, the location close enough to everything we would need . . .wish we could have stayed longer!
5.0
We hadn’t seen our family since Christmas 2019 because of the pandemic. My mother turned 102 on 11/21. This was our first experience renting online. We rented this house for its proximity to my moms.
We hosted 8 for a family brunch/ birthday party. The kitchen is very well equipped to cook in, ample seating and it’s cozy with the gas stove. Nice appliances and sharp knives(. I had brought mine but didn’t need them).
Things to be aware of : the building is old and historic . Take that into consideration when you arrive and look around. (Entrance looks it’s age. )Inside is darling.
Visiting in the winter: turn the stove on and both bathroom heaters upon arrival and the space warms up fast. The floor in the bath was cold so we put down three bath mats and it was fine. Turn the heat on in there when you get up.
Watch your head in the loft. once you are aware. it’s fine. We appreciated the night lights on the stairs. The loft is plenty warm at night. We have a queen at home so the size was fine for us and we found the mattress and pillows to be comfortable.
The back yard space would be great in warmer weather. A wide Brook runs through the property.
It’s close to two good markets, and high end liquor store. ( wine glasses and martini glasses provided.)
We would definitely rent this place again.
Thanks for the opportunity to review.
5.0
102nd birthday
We hadn’t seen our family since Christmas 2019 because of the pandemic. My mother turned 102 on 11/21. This was our first experience renting online. We rented this house for its proximity to my moms.
We hosted 8 for a family brunch/ birthday party. The kitchen is very well equipped to cook in, ample seating and it’s cozy with the gas stove. Nice appliances and sharp knives(. I had brought mine but didn’t need them).
Things to be aware of : the building is old and historic . Take that into consideration when you arrive and look around. (Entrance looks it’s age. )Inside is darling.
Visiting in the winter: turn the stove on and both bathroom heaters upon arrival and the space warms up fast. The floor in the bath was cold so we put down three bath mats and it was fine. Turn the heat on in there when you get up.
Watch your head in the loft. once you are aware. it’s fine. We appreciated the night lights on the stairs. The loft is plenty warm at night. We have a queen at home so the size was fine for us and we found the mattress and pillows to be comfortable.
The back yard space would be great in warmer weather. A wide Brook runs through the property.
It’s close to two good markets, and high end liquor store. ( wine glasses and martini glasses provided.)
We would definitely rent this place again.
Thanks for the opportunity to review.
4.0
Debated about leaving a review for it was a mixed bag staying there ~ Plus side: The Historic value/décor , Pet friendly, Big Yard for the dogs, Nice kitchen, Great location in the Berkshires and Lovely owners. Some things to think about: Hot water is limited. Great Historic Value, however, it is becoming tired, needs to be refreshed. Steep stairs. Bed is full size and sofa bed; not to good. Cleaning process wasn't complete when we got there, we were left a note by cleaning staff to finish what they couldn't. Lastly, the door was VERY hard to open via the key and door aliment. Again, I debated about leaving this review, however, we paid a lot to stay here and from the other reviews we thought we were getting a lot more for our money. If the things I wrote do not bother you, then this is a wonderful Historical place to stay. Our expectations were a little higher.
4.0
It was Nice ~
Debated about leaving a review for it was a mixed bag staying there ~ Plus side: The Historic value/décor , Pet friendly, Big Yard for the dogs, Nice kitchen, Great location in the Berkshires and Lovely owners. Some things to think about: Hot water is limited. Great Historic Value, however, it is becoming tired, needs to be refreshed. Steep stairs. Bed is full size and sofa bed; not to good. Cleaning process wasn't complete when we got there, we were left a note by cleaning staff to finish what they couldn't. Lastly, the door was VERY hard to open via the key and door aliment. Again, I debated about leaving this review, however, we paid a lot to stay here and from the other reviews we thought we were getting a lot more for our money. If the things I wrote do not bother you, then this is a wonderful Historical place to stay. Our expectations were a little higher.
5.0
Just Perfect
This was our second stay at the schoolhouse. It is a beautiful property both inside and outside. The house was completely furnished so we had everything we needed or wanted. We have family in the area and had plenty of room for them to stop by and visit. We will be back!
5.0
We LOVED staying at the school house! Quiet. Comfortable. Charming. Has everything you need. Close to everything and yet very private.
5.0
Perfect getaway
We LOVED staying at the school house! Quiet. Comfortable. Charming. Has everything you need. Close to everything and yet very private.
5.0
Just what we wanted for family assembling from New York and Boston areas. Easy to relax, eat in or out, enjoy the rushing stream in back and walks in nearby conservation areas, drive to Tanglewood or Williamstown, or eat at our favorite breakfast place in Lee, the Starving Artist. Three of the four of us are retired teachers who also enjoyed learning about the history of this restored, enhances one-room schoolhouse.
5.0
Spacious, clean, comfortable, and very charming.
5.0
Great location to all things Berkshire...
Just what we wanted for family assembling from New York and Boston areas. Easy to relax, eat in or out, enjoy the rushing stream in back and walks in nearby conservation areas, drive to Tanglewood or Williamstown, or eat at our favorite breakfast place in Lee, the Starving Artist. Three of the four of us are retired teachers who also enjoyed learning about the history of this restored, enhances one-room schoolhouse.
FAQs
How much does this house cost compared to others in Pittsfield?
The average price for a rental in Pittsfield is $199 per night. This rental is $109 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Featured in a Home & Garden TV Special 30 South Mountain Road. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Featured in a Home & Garden TV Special 30 South Mountain Road pet friendly?
Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Featured in a Home & Garden TV Special 30 South Mountain Road?
We found 11 amenities for this rental. This includes air conditioner, pets allowed, kitchen / kitchenette, internet / wifi, and fireplace.
Explore similar vacation rentals in Pittsfield
Explore all rentals in Pittsfield
3.9
Good(245 Reviews)Hotel
in Pittsfield3star
Best Western Plus Berkshire Hills Inn & Suites
Garden · Kitchen / Kitchenette · Air conditioner
The best choice in Pittsfield for Hotel, for $92 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
4.8
Outstanding(126 Reviews)House
in PittsfieldBeautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
25 guests · 8 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette
This attractive House in Pittsfield, $392 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
4.2
Excellent(948 Reviews)Hotel
in Lenox3star
The Yankee, Trademark Collection by Wyndham
Pool · Kitchen / Kitchenette · Air conditioner
Looking for the perfect place to call home during your trip to Pittsfield? This Hotel offers a comfort and style with top-notch amenities, including Air conditioner, Fireplace and Internet / Wifi, and more.
$$$$
5.0
Outstanding(95 Reviews)House
in PittsfieldBerkshire Pontoosuc Lake Beauty Too-Modern Amenities On The Lake
14 guests · 5 bedrooms · 4 baths
Garden · Kitchen / Kitchenette · Air conditioner
This House in Pittsfield, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
3.4
Average(348 Reviews)Hotel
in Lenox2star
Howard Johnson by Wyndham Lenox
Garden · Pool · Kitchen / Kitchenette
Nestled in Pittsfield, this Hotel is perfect for your next vacation. Enjoy Howard Johnson by Wyndham Lenox's top-rated amenities, including Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.
$$$$
5.0
Outstanding(87 Reviews)House
in PittsfieldModern 4 bedroom lakefront house in The Berkshires.
8 guests · 4 bedrooms · 4 baths
Garden · Kitchen / Kitchenette · Air conditioner
Looking for a House in Pittsfield, this House for $638 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
4.3
Excellent(349 Reviews)Hotel
in Lenox3star
Hampton Inn & Suites Berkshires-Lenox
Garden · Pool · Pets allowed
Experience vacation in Pittsfield with our Hotel, Hampton Inn & Suites Berkshires-Lenox. Enjoy amenities such as Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
5.0
Outstanding(71 Reviews)House
in PittsfieldTranquil Lake House Getaway on Onota Lake
10 guests · 5 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner
Experience the best of Pittsfield with this House available for $600. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
3.5
Average(393 Reviews)Motel
in PittsfieldBerkshire Inn
Pool · Kitchen / Kitchenette · Air conditioner
Looking for the perfect place to call home during your trip to Pittsfield? This Motel offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.
$$$$
4.8
Outstanding(85 Reviews)House
in PittsfieldSpacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
7 guests · 3 bedrooms · 3 baths
Garden · Pool · Pets allowed
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Pittsfield, at $285 per night for your next great vacation.
$$$$
4.6
Outstanding(68 Reviews)Hotel
in PittsfieldThe Central Downtown Inn Suites
Garden · Pets allowed · Kitchen / Kitchenette
Soak up the beauty of Pittsfield in our Hotel, The Central Downtown Inn Suites. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.
$$$$
4.9
Outstanding(61 Reviews)House
in PittsfieldBerkshire Lake House vacation home
6 guests · 4 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner
Looking for a House in Pittsfield, this House for $430 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
Hotel
in Pittsfield3star
Fairbridge Inn Express Pittsfield
Kitchen / Kitchenette · Air conditioner · Internet / Wifi
Looking to create some memories in Pittsfield? Look no further than our Hotel, Fairbridge Inn Express Pittsfield. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
4.8
Outstanding(75 Reviews)House
in PittsfieldBeautiful Waterfront home with deep water dock on Onota Lake
10 guests · 3 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner
Looking for a memorable stay in Pittsfield? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.
$$$$
3.1
Average(205 Reviews)Motel
in LenoxWagon Wheel Inn
Garden · Kitchen / Kitchenette · Air conditioner
Are you ready to indulge in a relaxing getaway? Our Motel in Pittsfield has everything you need for a rejuvenating stay. Treat yourself to Wagon Wheel Inn's exceptional amenities, such as Air conditioner, Internet / Wifi and Hot Tub / Spa.
$$$$
4.3
Excellent(187 Reviews)Hotel
in Pittsfield3star
Hilton Garden Inn Lenox Pittsfield
Pool · Pets allowed · Kitchen / Kitchenette
Nestled in Pittsfield, this Hotel is perfect for your next vacation. Enjoy Hilton Garden Inn Lenox Pittsfield's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
4.9
Outstanding(45 Reviews)House
in PittsfieldLake Front Home in Heart of the Berkshires Near Jiminy Peak
10 guests · 4 bedrooms · 4 baths
Garden · Kitchen / Kitchenette · Air conditioner
This inviting House in Pittsfield can fit your needs for many types of vacations, at $550 per night.
$$$$
4.3
Excellent(500 Reviews)Nature lodge
in PittsfieldBerkshire Mountain Lodge
Pool · Kitchen / Kitchenette · Air conditioner
Looking for a memorable stay in Pittsfield? Our Nature lodge might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.
$$$$
5.0
Outstanding(34 Reviews)House
in PittsfieldCasa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
14 guests · 5 bedrooms · 4 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi
Experience the best of Pittsfield with this House available for $500. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
3.7
Good(277 Reviews)Hotel
in Pittsfield4star
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Pool · Pets allowed · Air conditioner
Discover the beauty of Pittsfield with a stay at Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, a top rated Hotel with amenities such as Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
5.0
Outstanding(33 Reviews)House
in PittsfieldThis house is a 4 bedroom(s), 2.5 bathrooms, located in Pittsfield, MA.
12 guests · 4 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette
Looking for a House in Pittsfield, this House for $458 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
House
in DaltonDalton Vacation Rental Near Hiking and Skiing!
Kitchen / Kitchenette · Internet / Wifi · Parking
Looking for the perfect place to call home during your trip to Pittsfield? This House offers a comfort and style with top-notch amenities, including Dishwasher, Internet / Wifi and Kitchen / Kitchenette, and more.
$$$$
4.8
Outstanding(33 Reviews)House
in RichmondRichmond Pond Beauty
7 guests · 3 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner
Indulge in a peaceful retreat at Richmond Pond Beauty, our elegant House in Pittsfield. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
3.3
Average(27 Reviews)Motel
in PittsfieldHeart of the Berkshires Motel
Pets allowed · Kitchen / Kitchenette · Air conditioner
Looking to create some memories in Pittsfield? Look no further than our Motel, Heart of the Berkshires Motel. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
5.0
Outstanding(28 Reviews)House
in PittsfieldLakeside Home With Pool-Completely Renovated
16 guests · 6 bedrooms · 5 baths
Garden · Pool · Kitchen / Kitchenette
Discover the beauty of Pittsfield with a stay at Lakeside Home With Pool-Completely Renovated, a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
House
in PittsfieldPittsfield Home with Deck - 12 Mi to Jiminy Peak!
Kitchen / Kitchenette · Internet / Wifi · Parking
When traveling to Pittsfield, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $100 per night.
$$$$
5.0
Outstanding(25 Reviews)House
in PittsfieldA Private 1940s Elegant Estate, renovated to Modern-Day Luxury - Tanglewood
9 guests · 5 bedrooms · 5 baths
Garden · Pool · Kitchen / Kitchenette
Experience the best of Pittsfield with this House available for $1,700. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
House
in PittsfieldBerkshire Vacation Rentals: Chic Pittsfield Home With A View
Pets allowed · Kitchen / Kitchenette · Internet / Wifi
Discover the beauty of Pittsfield with a stay at Berkshire Vacation Rentals: Chic Pittsfield Home With A View, a top rated House with amenities such as Dishwasher, Fireplace and Internet / Wifi, and more.
$$$$
4.7
Outstanding(28 Reviews)House
in PittsfieldDancing Horse Lodge
6 guests · 3 bedrooms · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette
This inviting House in Pittsfield can fit your needs for many types of vacations, at $140 per night.
$$$$
House
in PittsfieldSpacious Historic Home in the Berkshires!
Pets allowed · Kitchen / Kitchenette · Air conditioner
Business stays, family stays, couples stay, getaway vacation, and rental in Pittsfield at Spacious Historic Home in the Berkshires! for $140 for your next trip.
$$$$
Pittsfield travel inspiration
Read our blogGuides
Ski Trip Packing List: What to Bring Skiing or Snowboarding
Trends
VacationRenter Holiday Travel Trends 2023
Featured Rentals
Architectural Vacation Rentals: Experience the Beauty of Unique Properties
Featured Rentals
Sustainable and Eco-Friendly Vacation Rentals Around the World
Featured Rentals
Our Favorite Vacation Rentals With Unique Experiences
Featured Rentals
Amazing Cabin Rentals Across the Globe
Featured Rentals
Have You Ever Wanted to Stay in a Dome Rental? Now You Can
Featured Rentals
Jaw Dropping Treehouse Rentals All Over the World
Keep exploring
- Lake Tahoe Cabins
- Ruidoso Cabins
- Blue Ridge Cabins
- Estes Park Cabins
- Lake George Cabins
- Eureka Springs Cabins
- Branson Cabins
- Lake of the Ozarks Cabins
- Lake Arrowhead Cabins
- Lake Texoma Cabins
- Canyon Lake Cabins
- Sevierville Cabins
- Flagstaff Cabins
- Colorado Springs Cabins
- Hot Springs Cabins
- Bass Lake Cabins
- Buffalo River Cabins
- Possum Kingdom Lake Cabins
- Chattanooga Cabins
- Nashville Cabins
- Wears Valley Cabins
- Cloudcroft Cabins
- Deep Creek Lake Cabins
- Mammoth Lakes Cabins
- Anna Maria Islands Rentals
- Outer Banks Vacation Rentals
- Rosemary Beach Rentals
- Holden Beach Rentals
- Hilton Head Vacation Rentals
- Topsail Beach Rentals
- Kiawah Island Rentals
- Panama City Beach Rentals
- Ocean Isle Beach Rentals
- Folly Beach Rentals
- Dauphin Island Rentals
- Rehoboth Beach Rentals
- Bethany Beach Rentals
- Cape Cod Rentals
- 30A Rentals
- Seaside Florida Rentals
- Edisto Beach Rentals
- Fort Myers Beach Rentals
- Miramar Beach Rentals
- Port Aransas Rentals
- Emerald Isle Rentals
- Orange Beach Rentals
- Surfside Beach Rentals
- Hampton Beach Rentals
- Assateague Island Rentals
- Jacksonville Beach Vacation Rentals
- North Shore Vacation Rentals
- Ogunquit Vacation Rentals
- North Redington Beach Rentals
- Lido Key Vacation Rentals
- Sea Colony Rentals
- Pass A Grille Vacation Rentals
- Blue Ridge Mountain Rentals
- Vail Lodging
- Jackson Hole Lodging
- Winter Park Lodging
- Telluride Lodging
- Big Sky Rentals
- Aspen Lodging
- Park City Rentals
- Steamboat Springs Lodging
- Breckenridge Rentals
- Lake Tahoe Rentals
- Copper Mountain Lodging
- Mammoth Mountain Lodging
- Beech Mountain Rentals
- Crested Butte Rentals
- Sun Valley Lodging
- Keystone Lodging
- Taos Lodging
- Sugar Mountain Cabins
- Beaver Creek Lodging
- Deep Creek Lake Rentals
- Smith Mountain Lake Rentals
- Ocean Lakes Rentals
- Lake Anna Rentals
- Torch Lake Rentals
- Lake Winnipesaukee Rentals
- Norris Lake Rentals
- Lake Gaston Rentals
- Canyon Lake Rentals
- Lake Oconee Rentals
- Lake Wallenpaupack Rentals
- Lake Martin Rentals
- Lake Havasu Rentals
- Lake of the Ozarks Rentals
- Lake Michigan Vacation Rentals
- Lake Chelan Rentals
- Finger Lakes Rentals
- Lake Keowee Vacation Rentals
- Lake Conroe Rentals
- Lake Erie Vacation Rentals
- Lake Austin Vacation Rentals
- Sebago Lake Rentals
- Lake Tillery Rentals
- Keuka Lake Rentals