Charming 3-bedroom house located on Main Street in Downtown Middlebury
9.4 / 10
Outstanding(28 Ratings)
$$$$
House in Indiana
9 guests · 3 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
Location
Reviews
8 / 10
There were no outdoor chairs in the backyard. Also there were bugs in the microwave and ants throughout the house. It was a nice house but the cleanliness was not top notch. A suggestion would be if the owners could leave a list of local places to eat and shop plus a place for buying groceries. Thank you.
10 / 10
This home very clean and charming. The host responded promptly to any questions we asked. Our 6 year old grandson enjoyed the bowling game in the basement. We enjoyed our stay.
10 / 10
My vacation party went from 5 people to 2; so one befroom and the extra living space/ game room was not used! However it was big enough to have a larger party where no one would have felt cramped! Since it was just me and my adult grandsons, we ate out every meal; however all of the utensils, pots and pans, dishes, etc., we're there- along with an ice maker. We did use the washer/dryer which saved me from doing laundry when I got home!The house was furnished well, and very comfortable! I would love to live there! The location was great! It was easy to find, close to everything, and even walking distance to some restaurants. My grandson ordered a pizza from Danny's and then walked down the street to pick it up! Very convenient! I love staying in vacation homes as my grandsons are adults, they dont want to share bedrooms and spaces with grandma! This home allowed us to spread out, be together if we wanted, or apart if we wanted to be alone! We loved our stay here and would love to come back, stay here, and see more of the town. We visited Shipshawana, Elkhart, Goshen, most all of the notable Amish restaurants, and of course the huge flea market and antiques stores. My opinion, skip the flea market and visit the unique stores in Shipshawana and Middlebury instead! I was disappointed in the offerings for antiques at the flea market. If you are an antique hunter, you need to skip the "fleas"- which is mostly Chinese or low grade junk.
10 / 10
Very nice place. Busy street, but fun to sit out front & watch the horse & buggies go by!
There were no outdoor chairs in the backyard. Also there were bugs in the microwave and ants throughout the house. It was a nice house but the cleanliness was not top notch. A suggestion would be if the owners could leave a list of local places to eat and shop plus a place for buying groceries. Thank you.
10 / 10Outstanding·Jul 2026
This home very clean and charming. The host responded promptly to any questions we asked. Our 6 year old grandson enjoyed the bowling game in the basement. We enjoyed our stay.
10 / 10Outstanding·Jun 2026
My vacation party went from 5 people to 2; so one befroom and the extra living space/ game room was not used! However it was big enough to have a larger party where no one would have felt cramped! Since it was just me and my adult grandsons, we ate out every meal; however all of the utensils, pots and pans, dishes, etc., we're there- along with an ice maker. We did use the washer/dryer which saved me from doing laundry when I got home!The house was furnished well, and very comfortable! I would love to live there! The location was great! It was easy to find, close to everything, and even walking distance to some restaurants. My grandson ordered a pizza from Danny's and then walked down the street to pick it up! Very convenient! I love staying in vacation homes as my grandsons are adults, they dont want to share bedrooms and spaces with grandma! This home allowed us to spread out, be together if we wanted, or apart if we wanted to be alone! We loved our stay here and would love to come back, stay here, and see more of the town. We visited Shipshawana, Elkhart, Goshen, most all of the notable Amish restaurants, and of course the huge flea market and antiques stores. My opinion, skip the flea market and visit the unique stores in Shipshawana and Middlebury instead! I was disappointed in the offerings for antiques at the flea market. If you are an antique hunter, you need to skip the "fleas"- which is mostly Chinese or low grade junk.
10 / 10Outstanding·Jun 2026
Very nice place. Busy street, but fun to sit out front & watch the horse & buggies go by!
Nestled in the heart of charming Middlebury, The Cozy Cottage on Main Street is the perfect family-friendly retreat for those looking to relax, explore, and make memories. This unique and welcoming home comfortably sleeps up to 8 guests, offering plenty of space to unwind while keeping you close to everything this beautiful area has to offer. Located downtown, you’ll have easy walking access to local restaurants, the renowned Pumpkinvine Trail, boutique shopping, and small-town charm. For those looking for adventure, we’re just 10 minutes from the famous Shipshewana Flea Market—a must-visit for treasure hunters and antique lovers —and only 40 minutes from the University of Notre Dame, perfect for game day weekends or campus visits. Inside, you’ll find warm, thoughtful touches that make the Cottage feel like home—from cozy living areas to a well-equipped kitchen, and sleeping arrangements suited for families or groups. Whether you’re enjoying a quiet morning coffee on the porch or gathering with loved ones after a day of exploring, this is a space designed for comfort and connection. Book your stay today and experience the perfect blend of relaxation and small-town adventure at the Cozy Cottage on Main Street!
Amenities
Non-smoking
No pets allowed
Family friendly
FAQs
Is parking included with this house?
Parking is not specified as an available amenity at Charming 3-bedroom house located on Main Street in Downtown Middlebury. 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 Charming 3-bedroom house located on Main Street in Downtown Middlebury pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Charming 3-bedroom house located on Main Street in Downtown Middlebury?
We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.
Charming 3-bedroom house located on Main Street in Downtown Middlebury
Top rated by guests
9.4Outstanding
(28 Ratings)
"This home very clean and charming. The host responded promptly to any questions we asked. Our 6 year old grandson enjoyed the bowling game in the basement. We enjoyed our stay."
Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Nestled in the heart of charming Middlebury, The Cozy Cottage on Main Street is the perfect family-friendly retreat for those looking to relax, explore, and make memories. This unique and welcoming home comfortably sleeps up to 8 guests, offering plenty of space to unwind while keeping you close to everything this beautiful area has to offer. Located downtown, you’ll have easy walking access to local restaurants, the renowned Pumpkinvine Trail, boutique shopping, and small-town charm. For those looking for adventure, we’re just 10 minutes from the famous Shipshewana Flea Market—a must-visit for treasure hunters and antique lovers —and only 40 minutes from the University of Notre Dame, perfect for game day weekends or campus visits. Inside, you’ll find warm, thoughtful touches that make the Cottage feel like home—from cozy living areas to a well-equipped kitchen, and sleeping arrangements suited for families or groups. Whether you’re enjoying a quiet morning coffee on the porch or gathering with loved ones after a day of exploring, this is a space designed for comfort and connection. Book your stay today and experience the perfect blend of relaxation and small-town adventure at the Cozy Cottage on Main Street!
Amenities
Non-smoking
No pets allowed
Family friendly
Map of Indiana
Ratings and reviews
9.4 / 10
Outstanding(28 Ratings)
8 / 10Excellent·Jul 2026
There were no outdoor chairs in the backyard. Also there were bugs in the microwave and ants throughout the house. It was a nice house but the cleanliness was not top notch. A suggestion would be if the owners could leave a list of local places to eat and shop plus a place for buying groceries. Thank you.
10 / 10Outstanding·Jul 2026
This home very clean and charming. The host responded promptly to any questions we asked. Our 6 year old grandson enjoyed the bowling game in the basement. We enjoyed our stay.
10 / 10Outstanding·Jun 2026
My vacation party went from 5 people to 2; so one befroom and the extra living space/ game room was not used! However it was big enough to have a larger party where no one would have felt cramped! Since it was just me and my adult grandsons, we ate out every meal; however all of the utensils, pots and pans, dishes, etc., we're there- along with an ice maker. We did use the washer/dryer which saved me from doing laundry when I got home!The house was furnished well, and very comfortable! I would love to live there! The location was great! It was easy to find, close to everything, and even walking distance to some restaurants. My grandson ordered a pizza from Danny's and then walked down the street to pick it up! Very convenient! I love staying in vacation homes as my grandsons are adults, they dont want to share bedrooms and spaces with grandma! This home allowed us to spread out, be together if we wanted, or apart if we wanted to be alone! We loved our stay here and would love to come back, stay here, and see more of the town. We visited Shipshawana, Elkhart, Goshen, most all of the notable Amish restaurants, and of course the huge flea market and antiques stores. My opinion, skip the flea market and visit the unique stores in Shipshawana and Middlebury instead! I was disappointed in the offerings for antiques at the flea market. If you are an antique hunter, you need to skip the "fleas"- which is mostly Chinese or low grade junk.
10 / 10Outstanding·Jun 2026
Very nice place. Busy street, but fun to sit out front & watch the horse & buggies go by!
$$$$
Top rated by guests
9.4Outstanding
(28 Ratings)
"This home very clean and charming. The host responded promptly to any questions we asked. Our 6 year old grandson enjoyed the bowling game in the basement. We enjoyed our stay."
Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
Map of Indiana
About this house rental
Nestled in the heart of charming Middlebury, The Cozy Cottage on Main Street is the perfect family-friendly retreat for those looking to relax, explore, and make memories. This unique and welcoming home comfortably sleeps up to 8 guests, offering plenty of space to unwind while keeping you close to everything this beautiful area has to offer. Located downtown, you’ll have easy walking access to local restaurants, the renowned Pumpkinvine Trail, boutique shopping, and small-town charm. For those looking for adventure, we’re just 10 minutes from the famous Shipshewana Flea Market—a must-visit for treasure hunters and antique lovers —and only 40 minutes from the University of Notre Dame, perfect for game day weekends or campus visits. Inside, you’ll find warm, thoughtful touches that make the Cottage feel like home—from cozy living areas to a well-equipped kitchen, and sleeping arrangements suited for families or groups. Whether you’re enjoying a quiet morning coffee on the porch or gathering with loved ones after a day of exploring, this is a space designed for comfort and connection. Book your stay today and experience the perfect blend of relaxation and small-town adventure at the Cozy Cottage on Main Street!
Amenities
Non-smoking
No pets allowed
Family friendly
FAQs
Is parking included with this house?
Parking is not specified as an available amenity at Charming 3-bedroom house located on Main Street in Downtown Middlebury. 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 Charming 3-bedroom house located on Main Street in Downtown Middlebury pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Charming 3-bedroom house located on Main Street in Downtown Middlebury?
We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.
Discover the beauty of Indiana with a stay at St Joseph River Retreat w/ Private Pool, a top rated House with amenities such as Kitchenware, Ironing facilities and Hairdryer, and more.
Business stays, family stays, couples stay, getaway vacation, and rental in Indiana at Hidden Log Cabin | Hot Tub | Ping Pong | Family | for $228 for your next trip.
When traveling to Indiana, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $246 per night.
Looking to create some memories in Indiana? Look no further than our Cabin, Cozy Amish Country Cabin on Shipshewana Lake!. Enjoy top-rated amenities including No pets allowed, Family friendly and Non-smoking, and more.
Experience vacation in Indiana with our House, Songbird Haven, 3 min from town, Pumpkinvine, MEC,concerts. 3 bedroom, 2 bath.. Enjoy amenities such as No pets allowed, Family friendly and Non-smoking, and more.
Looking for a Cottage in Indiana, this Cottage for $220 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
Looking to create some memories in Indiana? Look no further than our House, Relax with the whole family, peaceful and in the woods on 6 beautiful acres.. Enjoy top-rated amenities including No pets allowed, Family friendly and Non-smoking, and more.
Enjoy the best of Indiana in our Cottage, Waterfront Syracuse Home w/ Patio & Fire Pit!. A stunning property with amenities including No pets allowed, Family friendly and Non-smoking, and more.
Business stays, family stays, couples stay, getaway vacation, and rental in Indiana at Private Lake, Sleeps 11, Near Shipshewana, 4 Bedrooms, 2 Baths for $250 for your next trip.
Looking for the perfect place to call home during your trip to Indiana? This House offers a comfort and style with top-notch amenities, including No pets allowed, Family friendly and Non-smoking, and more.
Are you ready to indulge in a relaxing getaway? Our Cabin in Indiana has everything you need for a rejuvenating stay. Treat yourself to Twin Mills RV Resort's exceptional amenities, such as Non-smoking and No pets allowed.
Experience the best of Indiana with this House available for $207. This property is equipped with amenities including No pets allowed, Family friendly and Non-smoking, and more.
Nestled in Indiana, this House is perfect for your next vacation. Enjoy Newly updated 2023 home on Dallas Lake's top-rated amenities, including No pets allowed, Family friendly and Non-smoking, and more.
Nestled in Indiana, this House is perfect for your next vacation. Enjoy Quiet cul-de-sac home near Syracuse's top-rated amenities, including No pets allowed, Family friendly and Non-smoking, and more.
When traveling to Indiana, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $218 per night.
Business stays, family stays, couples stay, getaway vacation, and rental in Indiana at Treehouse Acres, Treehouse Acres Vacation Home for $241 for your next trip.
Looking for a memorable stay in Indiana? Our Cottage might just be what you're looking for. Enjoy amenities including Pets allowed and Non-smoking, and more during your stay.