5 Best Vacation Rentals In Middlebury, Vermont

Collins
Collins 
Updated
| 5 min read

Middlebury, a peaceful college town in the western part of Vermont, USA, is a beautiful and charming place. This small town is home to some of the most important art collections and has a lot of attractions and exciting places to experience. From exploring the oldest community museum in the country, surfing through the most beautiful art galleries, shopping at the great shops here, dining at exquisite restaurants and enjoying a wine-tasting trail hike, there are several relaxing things to do in Middlebury. And you can’t miss the waterfalls here too. Accommodation is not a problem either. The quaint town boasts of several inns, but if you need that home feeling, here is a list of the best Vrbo vacation rentals in Middlebury.

We handpicked these listings carefully, considering (wherever possible) Superhost status. recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 13, 2023.

1. Cozy home in the town center (from USD 395)

This comfortable vacation rental is a two-floor home right in the center of Middlebury. It is a three-bedroom, recently remodeled house with three full bathrooms and a half bathroom. It also has a spacious living room area, a dining room that can seat up to six guests, a fully equipped kitchen, a front porch and a back deck. The rooms are all tastefully furnished with its family room fitted with comfortable sofas, HD flatscreen TV and games for your entertainment. With a laundry room, and located just a few minutes’ walks from downtown Middlebury, this house is just perfect for a small group of up to eight people. Children are welcome and there is free Wi-Fi too!

Stayed at this property?
39 reviews   Wifi Available
House 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
Love the open air atmosphere and the way the bedrooms are set up
Neat as a pin throughout and plenty of
The open floor plan was perfect for not feeling confined in one room
the master bedroom has some lovely windows that allow for great light
convenient roomy and has everything that you need for a nice stay
Cleanliness:
Comfortable beds clean and overall lovely
The bedrooms were clean and comfortable
The house was very comfortable and inviting and completely well equipped
Very clean and comfortable Great kitchen
(1) although private the master bedroom (3rd floor) does not have a door (which allowed for a lot of noise pollution from the downstairs; something to be aware of if multiple groups are staying in...
Host:
Home Plate was a home run
What a perfect home base for our graduation celebration Ashley was accommodating and responsive
We cooked talked played cards and watched the Olympics
dining living area was great for our group to gather and hang out in the morning for events
We even got to host our son and some of his friends from school
Location:
the location is in walking distance of the main shopping district
It's an easy walk to Main Street Middlebury or the College and close to the supermarket and shops too
It's well located and about a 10 minute walk to everything One thing to note is parking
It is a nice house and is centrally located and walking distance to downtown Middlebury Middlebury College and the grocery stores
It's on a busy-ish street which had no other cars parked on it which made us nervous to park a car out on the street
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2. Incredible custom-built home (from USD 240)

Situated in an orchard in a beautiful and quiet neighborhood, this custom built home is an excellent place for a relaxing getaway. Its surrounding environment is serene and peaceful, with fresh orchards all around. This home has an intricately designed interior that is very well furnished with the best features for your comfort. It has three levels, three bedrooms, a main living area with a spacious private deck, a dining room and a fully stocked kitchen. There is an outdoor garden with chairs plus satellite TV with free Wi-Fi for your indoor entertainment. It is a great place to relax and enjoy the breathtaking gift of nature.

Stayed at this property?
Cornwall, VT, US
42 reviews  
House 6 Guests 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
beautiful architecture spacious yet cozy house with land and views
terrific showers washer and dryer exceptionally well appointed kitchen
choose to dine at the large indoor table or on the glorious huge balcony
Cleanliness:
the house was clean and well maintained
super comfy clean and bright
this lovely house is spotlessly clean comfortable well equipped
Host:
comfort is obviously the owners’ main concern
owner is super - responsive and friendly
owner is very responsive flexible and helpful
noel the property owner was very responsive and accommodating
beautiful views lovely house with every amenity very comfortable and owner very accommodating to our changing schedule
Location:
super close to middlebury
great art work perfect location for our family the function
the house is so comfortable and it is in a very convenient location
amazing home beautiful kitchen very comfortable and close to middlebury
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3. Large and luxurious farmhouse (from USD 1000)

If you are thinking of having a luxurious vacation with your large or extended family, then look no further than this majestic farmhouse. The house is a large and magnificent four-bedroom vacation rental, perfect for a family or group of friends. The newly-built edifice is so tastefully decorated and furnished, you’d not want to leave. Each of its bedrooms is en suite with glass showers; there is a snug den with fireplace, a game room, laundry room, fully equipped kitchen, a large patio and a private screened porch. Also, the house has a free internet connection, satellite TV and full air conditioning.

Stayed at this property?
12 reviews  
House 13 Guests 4 Bedrooms 5 Bathrooms

Accommodates: 13
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
sheep and two donkeys right outside that belong to a neighbor Drinking coffee in the early morning and listening to the cows
Host:
Home met and exceeded all of our expectations
You will never want to leave The home owner has done the most amazing renovation of any property I have ever seen Joanna Gaines would give them an A+
The home is gorgeous and extremely comfortable
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4. Historic downtown home (from USD 207)

One great thing about this lovely vacation rental is that it is located right in the heart of Middlebury. You can walk from this house to all the main places downtown. This apartment also has a lovely historic feel to it. It is beautifully furnished and recently updated with state-of-the-art appliances for your enjoyment. This home has three bedrooms, a living room area with a private deck, dining room, outdoor free parking and a well-stocked kitchen. Enjoy free internet connection and cable TV when you stay at this charming apartment during your vacation trip to Middlebury.

Stayed at this property?
9 reviews   Wifi Available
Apartment 8 Guests 3 Bedrooms 1 Bathroom

Accommodates: 8
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Easy and practical Everything was fine except for the very uncomfortable beds
Cleanliness:
It was clean and well stocked and an easy walk to everything in MIddlebury
Location:
An excellent and comfortable house in a great location
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5. Charming cottage on the creek (from USD 202)

This beautiful vacation rental is a lovely, newly built cottage on an expansive landscape. It is a few minutes’ walks from town with bicycles provided for those who’d prefer to bike into town. It is very cozy and features beautiful views of the creek. With its two bedrooms, spacious family room with a fireplace, well-equipped kitchenette, private screened porch and private canoe for forays into town, this apartment is the ideal place for a romantic getaway. It is private, pristinely furnished and very peaceful.

Stayed at this property?
43 reviews   Wifi Available
cottage 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Kitchen is well equipped with pots and pans
The cottage is new has comfortable beds and is stocked with anything you would need
The bed was very comfortable and the screened in porch overlooks the creek and the beautifully landscaped lawn
The screened-in porch is great as the weather improves
Very peaceful property and living space - with everything we needed
Cleanliness:
I especially appreciated the well stocked and fully functional kitchenette; I was able to cook and bake quite a lot
Everything was just as described and extremely cozy
Although very clean and located in a lovely part of Middlebury fronting water and beautiful gardens
The cottage is extremely clean and very well furnished with all the facilities that one desires
Charming cottage with lovely views of the Creek
Host:
They provided me with bike maps and routes and all the information I required to enjoy Middlebury and its surroundings
Clean warm comfortable Also excellent communication with Zelia and Gary
Zelia and Gary were warm and welcoming Great advice on bike routes and restaurants in the area
Zelia and Gary couldn't have been more friendly and helpful
We felt the ambiance could have benefited from some upholstered furniture such as a loveseat or sofa and some art on the wall Done in minimalist fashion and not by any sense of the word cozy ...
Location:
It takes about 20 minutes to walk to the centre of Middlebury from there
The location is nice with a pleasant walk into town (sidewalks are being put in now to cover the whole way) or to the College
It was a pleasure to come back to this property after a day of exploring this beautiful part of Vermont
(The end of the garden meets Otter Creek--we were brave enough to try the canoe once )
Zelia and Gary have built a small but lovely cottage in their spacious garden in Middlebury
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Experience a peaceful getaway

The quiet town of Middlebury is an exciting place to visit. With incredible attractions all year round, it is a great place to relax, explore, and enjoy the beautiful gifts of a naturally scenic landscape. Whether you are hiking through the exciting outdoor trails, shopping in the quality local stores or dining at the exquisite restaurants here, you are sure to have a wonderful time in this peaceful and historic town. Just book any of the above Vrbo vacation rentals in Middlebury and enjoy an unforgettable holiday.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Colins is a quiet individual who always tries to find the meaning and beauty of things around his environment. This passion has led him to begin his journey in photography and hiking nature...Read more

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