Holiday rentals in Middlebury

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Popular amenities for Middlebury holiday rentals

Stay near Middlebury's top sights

Two Brothers Tavern13 locals recommend
Fire & Ice21 locals recommend
Middlebury Natural Foods Co-Op13 locals recommend
Shaw's6 locals recommend
Woodchuck® Cider12 locals recommend
Lincoln Peak Vineyard10 locals recommend

Other great holiday rentals in Middlebury

Superhost
Home in Warrensburg
4.85 out of 5 average rating, 233 reviews

INCREDIBLE 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 reviews

Secluded 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 reviews

Beautiful 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 reviews

Modern 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 reviews

100 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 reviews

Lovely 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 reviews

Edin'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 reviews

Luxury 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

  1. Airbnb
  2. United States
  3. Vermont
  4. Addison County
  5. Middlebury