Middlebury vacation rentals

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Popular amenities for Middlebury vacation rentals

Stay near Middlebury's top sights

Middlebury College43 locals recommend
Two Brothers Tavern64 locals recommend
Fire & Ice53 locals recommend
Middlebury Natural Foods Co-Op46 locals recommend
The Otter Creek Brewery43 locals recommend
Shaw's40 locals recommend

Other great vacation rentals in Middlebury

Superhost
Home in Warrensburg
4.85 out of 5 average rating, 231 reviews

INCREDIBLE Adirondack Home (Lake George/Gore Mtn.)

RachelRating, 5 stars1 day ago
We loved our stay, the house was perfect for what we needed. Beautiful view from the back porch, clean, cute decor, lots of space and the kitchen had all we needed. Easy drive to Gore mountain. Easy entry and contact with owners. We will definitely rent again!
Superhost
Condo in Warren
4.75 out of 5 average rating, 16 reviews

Tranquil Vermont Farmhouse Condo with Hot Tub

AnthonyRating, 5 stars2 months ago
Awesome property. Perfect location for a ski trip in Sugarbush. The apartment is spacious and can totally accommodate a large group. What stood out is that every room has its own television where everyone can enjoy. Moreover, the hot tub jacuzzi is a heaven especially after a brutal ski day. It is accessible to shops and restaurants. An accessible location where the shuttle from the ski resort can pick you up and drop you off is a gem, which takes away driving towards the resort. Our group will definitely be back before this winter season ends. We totally love this place.
Superhost
Home in Stowe
4.94 out of 5 average rating, 66 reviews

Charming and quiet rental for family or friends

BrianRating, 5 stars2 months ago
Liza’s home was beautiful, and it couldn’t be closer to Stowe Mountain Resort. It was the perfect ski trip house for my group, and the host was incredibly accommodating and helpful.
Guest favorite
Home in Woodstock
4.92 out of 5 average rating, 25 reviews

Great Maples

CatherineRating, 5 stars3 weeks ago
We loved our stay at Great Maples and are already thinking about booking another trip. We shared the house with another young family, and it worked out great. Plenty of space, clean, and beautiful. Private and relaxing but also lots of fun activities in neighboring towns. It even had a playroom and lots of books and toys for our kids. We can’t wait to go back!
Guest favorite
Home in Chestertown
5 out of 5 average rating, 10 reviews

Secluded and Cozy Townhome near Tripp Lake

NicoleRating, 5 stars7 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 stars2 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 favorite
Apartment in Burlington
4.97 out of 5 average rating, 67 reviews

Lovely 1 bedroom

Tyson & Tara GranlieRating, 5 stars5 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 favorite
Chalet in Jay
4.96 out of 5 average rating, 126 reviews

Edin's Chalet Adirondacks-Whiteface 4 Beds-2 Baths

VrushikRating, 5 stars1 week ago
A Magical Cabin Experience Our stay at this rustic cabin captivated us from the start. The warm exterior lighting at night created a fairytale ambiance. Spacious and beautifully decorated, the cabin featured a large stone fireplace for cozy evenings. Authentic yet modern wooden interiors, clean and well-maintained, provided everything we needed. The kitchen and dining area were perfect for relaxation. Stepping outside at night, we were amazed by the stunningly clear sky and even caught a glimpse of Orion’s Belt. The outdoor deck and seating area offered peaceful surroundings. I highly recommend this cabin for a relaxing retreat. Whether you’re a couple seeking romance or a family wanting quality time, it has it all.

Quick stats about vacation rentals in Middlebury

  • Total rentals

    60 properties

  • Nightly prices starting at

    $70 before taxes and fees

  • Total number of reviews

    4.5K 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