
Holiday rentals in Middlebury
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Middlebury
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Middlebury
Superhost

Home in Warrensburg
4.85 out of 5 average rating, 233 reviewsINCREDIBLE Adirondack Home (Lake George/Gore Mtn.)
MrRating, 5 stars1 month ago
Everything as described. Easy to find. Easy parking. Private and well equipped. Host quick to respond.
Guest favourite

Home in Chestertown
5 out of 5 average rating, 10 reviewsSecluded and Cozy Townhome near Tripp Lake
NicoleRating, 5 stars9 months ago
We really enjoyed staying at the condo in Green Mansions. It was very spacious and Bryce was extremely communicative.
Superhost

Villa in Stowe
4.82 out of 5 average rating, 45 reviewsBeautiful 5 Bedroom Villa with Amazing Views
RichardRating, 5 stars3 months ago
Very nice home with great amenities. Great location to and from everything. Nicely distributed with space for everyone. Beds were comfortable and the home has plenty of towels etc. Overall it was a great place for weekend or longer. Maria was easy to communicate with and there were no issues.
Top guest favourite

Home in Chittenden
5 out of 5 average rating, 8 reviewsModern Retreat next to Mountain Top Inn,Killington
MaddyRating, 5 stars2 months ago
I couldn't recommend this place more! My cousins and I had a great time and Uli is super attentive. The hot tub has a great view of the lake, it was also salt water which I love. The space was extremely cozy and exactly what we needed. We snowboarded pico and killington and it was about a 25-30 minute ride. We will for sure be back! Thank you guys so much!
Superhost

Cabin in Bridgewater
4.91 out of 5 average rating, 100 reviews100 Acres Views & Creek near Woodstock/Killington
ChristopherRating, 5 stars1 month ago
Had a great stay with friends at Laura’s place. Laura was friendly flexible and reached out to make sure we didn’t have any issues checking in. Very nice place with a nice Vermont feel. 10-15 minutes from skyeship base. Had a great weekend. Would stay again.
Guest favourite

Flat in Burlington
4.97 out of 5 average rating, 67 reviewsLovely 1 bedroom
Tyson & Tara GranlieRating, 5 stars6 months ago
Highly recommended space and host! Kurt is hands down an A+ super host! We arrived in Burlington in the evening with having another Airbnb reservation that we found not to be a good fit for us! Frantically searching for other Airbnb accommodations for the night, several hosts had availability but showed no urgency to help us. Kurt literally stopped what he was doing to go and turn lights and heat on for us. He also left water, a couple beers, and creamer in the fridge for our morning coffee, which too was provided. The space is exactly how it was pictured. Clean, uncluttered, and beautiful! Kurt’s place has great location in a charming quiet neighborhood with driveway parking. Comfortable bed and great water pressure in the shower was also great to have! Finding this place last minute was the cherry on top of our amazing Burlington experience….and we will be back! Thanks again
Top guest favourite

Chalet in Jay
4.96 out of 5 average rating, 129 reviewsEdin's Chalet Adirondacks-Whiteface 4 Beds-2 Baths
LelandRating, 5 starstoday
The house was very nice & it was set up very nicely. Nice location would be great to rent again.
Top guest favourite

Home in Plymouth
5 out of 5 average rating, 16 reviewsLuxury Modern Cabin near Okemo & Killington
TariQRating, 5 stars1 month ago
Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!
Quick stats about holiday rentals in Middlebury
Total rentals
70 properties
Nightly prices starting at
£53 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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- Okemo Mountain Resort
- Sugarbush Resort
- Smugglers' Notch Resort
- Spruce Peak
- Gore Mountain
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Whiteface Mountain Ski Resort
- Cochran's Ski Area
- Northeast Slopes Ski Tow
- Fort Ticonderoga
- Ethan Allen Homestead Museum
- Country Club of Vermont
- Montshire Museum of Science
- Lucky Bugger Vineyard & Winery
- Fox Run Golf Club
- Cozy Cottages & Otter Valley Winery
- Killington Adventure Center
- Lincoln Peak Vineyard
- Burlington Country Club
- Adirondack Extreme Adventure Course
- Leahy Center for Lake Champlain
- Vermont National Country Club
- Autumn Mountain Winery