Chestertown's Pet-Friendly Little Red Cottage
About this house rental
Nestled in Chestertown, this lovely house for $235 per night is a fantastic choice for your next vacation. Our darling, historic cottage, recently featured on Chestertown's Historic House Tour, is comfortable, pet-friendly and contemporary (on the inside!). It's a superb central-to-everything location, and one of the few perfectly pet-friendly rentals in town. And speaking of which: Chestertown is an event town – there’s something going on almost every weekend. Certainly, every First Friday of the month, all year long, is special. And our Little Red Cottage is at the heart of the activity (a heads up: On VRBO it says we’re about .8 miles from Chestertown’s center. It’s wrong. We’re more likely to be 8 steps – and we’re working with VRBO to correct). Beyond that? If you’re considering a visit over one of our town’s very, very special event weekends, you’ll want to plan ahead to reserve these dates (those dates not mentioned are already booked, alas). Otherwise, key details about our darling cottage: It's in the heart of Chestertown -- literally a block from both shops and restaurants and our waterfront -- we're pet-friendly with a fenced-in backyard. The house is recently renovated and has all modern conveniences, such as a new kitchen and bathroom -- and, best of all, a sociable front porch which is great for people-watching (and meeting locals and visitors alike). The cottage consists of a cozy living room with flat screen television (and Amazon Fire and WiFi), an eat-in dining room, and brand new kitchen on the first floor. Upstairs, one bedroom overlooks the gorgeous back garden of Chestertown's White Swan Tavern (a b&B/inn). The other overlooks are deep, fenced-in backyard. There's a bathroom -- stripped to the studs and rebuilt -- that offers a deep tub/shower combo. Out back, we've got a grill and a wicker-style dining table for four. There's also a seating area with Adirondack chairs and outdoor firepit and beyond that a cute little round picnic table. Our front porch is sublime. It's an ideal place to people watch and hang with our friendly neighbors. Historic Chestertown, about 1.5 hours from Philadelphia, Baltimore and Washington DC is an incredibly special place. It's located on the Chester River, a tributary off the Chesapeake Bay, and George Washington and Thomas Jefferson (according to a fabulous story in Garden and Gun Magazine, which named Chestertown one of the south's top 10 towns) both ate, slept and imbibed there. Chestertown is probably best known as the home of Washington College, a suburb institution that lends our town character, culture, sport, and arts. We're also home to the Schooner Sultana, a reproduction vessel from the mid 18th century, which is also part of a larger, and thriving, environmental program. Chestertown is a Main Street Community and has a thriving arts district. What else? We're home to annual events like the Chestertown Tea Party, the Harry Potter Festival, and Downrigging Weekend. We're a great destination for mariners, whether your idea of bliss is a swanky yacht or a sleek kayak.
Amenities
Air conditioner
Pets allowed
Kitchen / Kitchenette
Internet / Wifi
Laundry
Balcony / Patio
Dishwasher
TV
Garden
Map of Chestertown, MD
Reviews
4.9/5.0
Outstanding(43 Reviews)
5.0
The little red house is comfortable, tastefully decorated, with a well-equipped kitchen and heat pumps in every room. It's right in the heart of Chestertown, walking distance from everything we wanted to do. The owners cared very much about our comfort, and should we have needed anything more--which we didn't--they would have responded immediately.
3.0
We enjoyed our stay.
5.0
What a perfect experience! We loved Chestertown and the accomdations were excellent. The home is well maintained and has everything you need for a comfortable stay. And, the owner.....how VERY friendly and helpful! So nice to have a secure fenced-in yard for our dog. Parking was never a problem. The neighbors are very friendly and welcoming. It's a short walk to the river. The town is perfect for walking (with or without your dog). I have nothing negative to say about our week in Chestertown except that we should have stayed longer.
5.0
The location and property were amazing! Carolyn, the owner, was so accommodating!
5.0
We stayed for a lovely week. We walked our dogs down to the park and river every day. Walked to town every day for coffee shop, ice cream store, bookstore, or dinner. Spent time on front deck. Wifi was great as I worked on laptop each day. Owner communication was great.
5.0
We had a great time during the Memorial Day weekend with my wife, son and his girlfriend. Sensational location right in downtown, Chestertown being a beautiful historic little town. Close to good restaurants and shops. The house is very well equipped, very clean, with everything you could need for a short stay (we missed an electric kettle, though - that would be a nice addition for our next visit). Communication with Carolyn was excellent too. Besides, the handbook she put together is very complete and useful. The listing is accurate but cannot possibly describe the charm of this little, very warm house. We'll be back...
5.0
Loved our stay! Comfortable and inviting.
4.0
What a great location. So much within walking distance of this property. Very clean and neat historic property
5.0
Exceptionally cozy and quaint house. Sat on porch for morning coffee and evening wine, and friendliest passersby said good morning. Church bells gently chimed on the hour. Aroma from brick oven three doors away so inviting, great waffles breads bagels (call Monday/Tuesday to order Friday pizza); and the best French wine/cheese shop two paces from there. The house was sweet, kitchen well equipped, backyard as fun hanging out as the front porch. Our fury pets were also charmed and so at home. We want to return and enjoy the great restaurants we missed, take more walks around town, and sit on the front porch and enjoy the friendliest spot in America. What a great time thanks to owner Carolyn.
5.0
This was a perfect getaway to rest and recharge.
5.0
So nice to be able to bring our dog Cali to Chestertown! Very dog friendly town btw. Great location right in town so you can walk to everything. Home had everything we needed, including a sweet front porch to relax on. It was very hot during our stay so really appreciated the AC in the house. Would definitely visit the Red Cottage again!
5.0
Comfortable, very clean and updated historic city house with large private yard and nice front porch. Listing and photos very accurate.
Kitchen has everything you need! bathroom and bedrooms are upstairs and have a step and grade change. AC in every room ensures comfort for all. Great WiFi.
Easy street parking in a quiet neighborhood and steps to everything Chestertown has to offer. Great coffee and bakeries, restaurants and wine tastings.
5.0
Great weekend celebrating my daughter’s college graduation from Washington College!
Carolyn was great to work with and she was quick to reply to any questions! Even left us a nice bottle of wine from the local wine store! The house was adorable, clean and the bonus of my pup being included was extra special!
5.0
the property is delightful and perfect for 4 adults and a toddler. not a big house, but comfortable and well designed.
5.0
an enjoyable 3 day weekend with family
the property is delightful and perfect for 4 adults and a toddler. not a big house, but comfortable and well designed.
5.0
This house is right in the middle of shopping, restaurants, and all of the things to do and see in town. It has a great dining room and comfortable living room. There is only one bathroom and it is upstairs so hard for my elderly father to go up and down. Also the kitchen is nice but not equipped for real cooking. We found 4 dog bowls in the cabinet but no mixing bowls! But it is very dog friendly! All in all a very comfortable stay convenient to Heron Point where my dad lives.
5.0
Great Location, Nice Little House
This house is right in the middle of shopping, restaurants, and all of the things to do and see in town. It has a great dining room and comfortable living room. There is only one bathroom and it is upstairs so hard for my elderly father to go up and down. Also the kitchen is nice but not equipped for real cooking. We found 4 dog bowls in the cabinet but no mixing bowls! But it is very dog friendly! All in all a very comfortable stay convenient to Heron Point where my dad lives.
5.0
Lovely long weekend
My husband and I had a lovely time at this charming property. It's in a great location, and the house was comfy and well-equipped. It was a hot weekend, but the air conditioning worked great and the house was a lovely retreat in the city! A fantastic location- walking distance to everything. We will definitely stay again!
5.0
Chestertown is a quaint old town. The owner was very helpful, she even was willing to pick up the flowers that I ordered my wife for our anniversary. She had them on the dining room table when we arrived. She kept us very informed.
5.0
We are in love with this little cottage. It is cozy and homey. Carolyn was wonderful! We have booked again for October. Can't wait!
5.0
We truly enjoyed our stay at the red cottage! The front porch was the absolute best place to have coffee. The back yard is a lovely spot for grilling and having dinner. The house is beautifully decorated along with all the essentials that you would need. The cottage is located in the perfect location close to all the shops and restaurants. It is just walking distance to the Chester River too.
5.0
Special get away
Chestertown is a quaint old town. The owner was very helpful, she even was willing to pick up the flowers that I ordered my wife for our anniversary. She had them on the dining room table when we arrived. She kept us very informed.
5.0
Chestertown beauty!
We truly enjoyed our stay at the red cottage! The front porch was the absolute best place to have coffee. The back yard is a lovely spot for grilling and having dinner. The house is beautifully decorated along with all the essentials that you would need. The cottage is located in the perfect location close to all the shops and restaurants. It is just walking distance to the Chester River too.
5.0
Very enjoyable. AC was extremely important
5.0
Dan
Very enjoyable. AC was extremely important
5.0
Wonderful
We are in love with this little cottage. It is cozy and homey. Carolyn was wonderful! We have booked again for October. Can't wait!
5.0
Delightful cottage in quaint town
It may be hard to leave this front porch, with friendly passers-by, comfie chairs and a rose garden. But this sweet cottage is perfectly located, with restaurants, historic neighborhoods, the town square, and the waterfront a block or two away in each direction. Excellent hosts. Well appointed. It is a petite structure, particularly the staircase, so fine for us but worth noting. New bath and kitchen, big back yard, and lovely main floor. Ideal quiet getaway PLUS I could bring my dear doggie.
5.0
We had a wonderful, relaxing time at this affordable period cottage. It's got quirky architecture, a lovely front porch and a fantastic back yard... not to mention it's just a few steps from everything downtown Chestertown has to offer. The cottage even has friendly neighbors who we really enjoyed meeting! Also, Carolyn, the owner, is super helpful and sweet, and also left us alone to enjoy our stay - a perfect balance. Thanks for a wonderful stay!
5.0
I would give more than 5 stars if I could!
We had a wonderful, relaxing time at this affordable period cottage. It's got quirky architecture, a lovely front porch and a fantastic back yard... not to mention it's just a few steps from everything downtown Chestertown has to offer. The cottage even has friendly neighbors who we really enjoyed meeting! Also, Carolyn, the owner, is super helpful and sweet, and also left us alone to enjoy our stay - a perfect balance. Thanks for a wonderful stay!
5.0
Wonderful Weekend
We had a great weekend in the Little Red Cottage! There was plenty of room for our family of 4 and the layout is perfect. 2 bedrooms and a bathroom upstairs, plus a living room, dining room, and large kitchen downstairs. House was warm and parking was easy. Less than a block from Evergrain and other nice spots in Chestertown. Highly recommend.
5.0
Absolutely lovely!
Would definitely recommend this adorable cottage! The owners were very nice and easy to communicate with, the house was clean and comfortable, the front and backyards were both very cozy, and it's only a few steps away from local shopping. I also appreciated the recommendations of things to do -- the Saturday farmer's market was great! I would rent this place again.
5.0
Stay and walk
Great location for walking to river, cafes, historic tours, and for biking, too. Brand new kitchen!
5.0
Short lovely stay in Chestertown
The cozy red cottage is as described. A one block walk to the wine and cheese store, to Play it again Sam where we go our morning bagel and egg sandwiches, enjoyed sitting on the front porch with our pup, parking on the street was no problem. It’s a special place!
5.0
Wonderful getaway!
This was our first visit to Chestertown and it was wonderful! Carolyn was very accommodating and the house had everything we needed for a weekend getaway! Fenced in yard was perfect for our two dogs. Within walking distance to everything, shopping, restaurants, water. Neighbors were very friendly as well. We will definitely be staying here again!
5.0
What a lovely cottage it is!
My sister and I stayed for 4 nights in late May 2019. The house is adorable and comfortable and has everything you need.
It was a quiet weekend and we spent most of our time on the front porch (high temps & RH).
I would love to return in the autumn and bring a bicycle.
It was great to meet you Carolyn and thank you for allowing us to stay in your lovely home.
5.0
Cute Chestertown Cottage
The house was really a wonderful little place that was great for my family of three plus our small dog. The location is great and within walking distance to everything in town and on the water.
5.0
The property was beautiful and we had a fantastic time in an amazing little town!
We had an extremely positive visit and would definitely stay in this house again.
4.0
Lovely, cozy home.
Immaculate, uncluttered, well appointed, pretty home and garden space. Climate control (a/c or heat) in each room. Great location — walk to everywhere. Cotton bedding and comfortable mattresses. Owner kind and responsive.
5.0
Clean, comfortable, and full of character. Loved the location and outdoor spaces.
Perfect house for a weekend trip for a wedding. Enjoyed being able to walk to everything and relaxing on the front porch. Hosts were great and the house has everything you need for a stress free getaway.
5.0
The epitome of historic Chestertown.
This very lovely house is located right in the center of the historic district in Chestertown and a couple of blocks from the waterfront. Parking is plentiful, either directly in front of the house or a very short walk to a free parking area. The house is newly renovated, with beautiful original wood floors on the first and second floors. The kitchen is immaculate, with new cabinets, granite counter tops, and appliances. The fully fenced back garden, right outside the kitchen door is private and beautiful with plentiful seating areas in sun and shade. It reminds me of my father-in-law’s garden in England. When we are able to return, I hope that there are available dates to rent this property again. Robert and Ann
FAQs
How much does this house cost compared to others in Chestertown?
The average price for a rental in Chestertown is $199 per night. This rental is $36 above the average.
Is parking included with this house?
Parking is not specified as an available amenity at Chestertown's Pet-Friendly Little Red Cottage. 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 Chestertown's Pet-Friendly Little Red Cottage 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 Chestertown's Pet-Friendly Little Red Cottage?
We found 9 amenities for this rental. This includes air conditioner, pets allowed, kitchen / kitchenette, internet / wifi, and laundry.
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