
Places to stay in Middlebury
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Top-rated places to stay in Middlebury
Guests agree: these places to stay are highly rated for location, cleanliness, and more.
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Popular amenities for Middlebury places to stay
Other great vacation rentals in Middlebury
Top guest favorite

Apartment in Bristol
4.97 out of 5 average rating, 73 reviews2-Bedroom , 1 1/2 Bath Apartment with Mt Views.
GaryRating, 5 stars1 month ago
Amazing,Perfect,Comfortable,Everything you could ever need! Very clean. Perfectly located. Cheryl and Dan were fantastic hosts and went above and beyond to make our stay a very memorable one. We were treated like family, and we felt like we have known them for years. We would highly recommend them. And will “definitely “ rebook with them in the future. Their home is beautiful ( just as the pictures show and is described perfectly). We can’t thank them enough for making our extended Mother’s Day weekend with our children a special, memorable and enjoyable trip. You won’t be disappointed! Thank you so much…Gary, Christine, and Kim Bolk
Top guest favorite

Apartment in Vergennes
4.91 out of 5 average rating, 22 reviewsLittle City Brick Apartment A
UdayRating, 5 stars3 weeks ago
Curtis was very responsive to a concern we raised about the heater in the bedroom not turning on. He brought his handyman with him and sorted out the issue in short order. His desire to make us feel comfortable was not lost on us and we would definitely consider staying here again if our travel plans bring us back to Vergennes.
Top guest favorite

Apartment in Middlebury
5 out of 5 average rating, 18 reviewsUpdated Apartment Downtown
LucyRating, 5 stars1 week ago
Katherine’s apartment was so lovely, and perfect for our stay in Middlebury. It’s beautifully situated— we walked to and from town every night for dinner, and easily drove to explore the nearby lake and hiking trails—and the apartment itself is so clean and bright and comfortable! Every kitchen and toiletry item we could have needed is supplied, and the entrance to the apartment is very private. Katherine is very communicative and kind, and we felt thoroughly taken care of. We’ll be staying again next time we’re visiting Middlebury. Thank you for a wonderful stay!
Top guest favorite

Home in New Haven
4.97 out of 5 average rating, 37 reviewsUnique Serenity - 10 mins from Middlebury College
DaltonRating, 5 stars3 weeks ago
What a wonderful stay we had. The space is so clean and every amenity is thought of. Comfortable beds, great showers, and very close to Middlebury. Wish the weather had been better so we could have enjoyed the outdoor space more, but that will be for next time!
Top guest favorite

Home in Middlebury
5 out of 5 average rating, 33 reviews3 story contemporary log cabin
Douglas KennethRating, 5 stars3 weeks ago
We had a wonderful stay at Kurt’s place for Middlebury graduation. The house is very comfortable and had everything we needed for the weekend. Although it is about a 10 min drive from Middlebury, it is an easy drive and didn’t seem that far.

Home in Weybridge
5 out of 5 average rating, 4 reviewsUpdated farmhouse minutes from Middlebury
DianeRating, 5 stars1 week ago
Hands down one of the best Air B and Bs I’ve been to, and I’ve been to a lot! Mary and Luis, our hosts, were so welcoming that we instantly felt like family. Their communication was great. We had an incredible stay at their charming, beautifully updated farmhouse in Vermont! The home is full of character, with thoughtfully curated antique decor that gives it a warm, welcoming feel. Every detail has been considered, from cozy linens and a fully stocked kitchen to extra touches that made our stay especially comfortable. The views from the property are stunning, with rolling hills and peaceful scenery in every direction. We loved being able to walk to downtown Middlebury—just a short stroll away—for great shops, restaurants, and a true New England village vibe. This place is the perfect blend of rustic charm and modern comfort. Whether you're relaxing indoors or enjoying the scenery outside, you’ll feel right at home. I highly recommend and would return in a heartbeat!
Top guest favorite

Home in Middlebury
4.96 out of 5 average rating, 80 reviewsWalk Everywhere and Enjoy a Historic Vermont Home
ChristinaRating, 5 stars3 weeks ago
We loved our stay at Jeffrey's place. The house was perfectly located with easy access to the adorable town of Middlebury and the college campus. We were there for graduation weekend and were so grateful to have a cozy, clean, accommodating house to return to after all the festivities, without having to drive far. We were even able to walk to many events. The house was very clean with lots of space and everything we needed for our stay. Jeffrey left very clear instructions and great recommendations for walks, restaurants and more.
Top guest favorite

Apartment in Middlebury
5 out of 5 average rating, 143 reviewsBluebird Studio- Light filled and airy
AbbyRating, 5 stars3 weeks ago
Dutton’s place was perfect. We came for Middlebury’s commencement with our 6 year old and the location was excellent and quiet. Our son loved how cozy it was. The kitchen was really great to have on such a busy weekend. Dutton was super flexible and helpful too, letting us stay a few extra hours so our grad could finishing packing up her room. The bed was firm, just good to know. We all slept well. Absolutely recommend.
Quick stats about vacation rentals in Middlebury
Total rentals
70 properties
Nightly prices starting at
G$14,640 GYD before taxes and fees
Total number of reviews
4.7K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Yurt Rentals United States
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- Castle Rentals United States
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- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
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- Big House Rentals United States
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- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
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- Beach Cabins United States
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- Beach Houses United Kingdom
- Beach Villas United Kingdom
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- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Sugarbush Resort
- Okemo Mountain Resort
- Smugglers' Notch Resort
- Gore Mountain
- Bolton Valley Resort
- Spruce Peak
- Pico Mountain Ski Resort
- Cochran's Ski Area
- Fort Ticonderoga
- Whiteface Mountain Ski Resort
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Fox Run Golf Club
- Montshire Museum of Science
- Leahy Center for Lake Champlain
- Cozy Cottages & Otter Valley Winery
- Vermont National Country Club
- Ethan Allen Homestead Museum
- Country Club of Vermont
- Lucky Bugger Vineyard & Winery
- Adirondack Extreme Adventure Course
- Killington Adventure Center
- Burlington Country Club
- Lincoln Peak Vineyard