Holiday rentals in Middlebury

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Top-rated holiday rentals in Middlebury

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Cottage in New Haven
Small New Haven Cozy Cottage
This very small, compact cottage is in a rural setting, off the beaten path. It is about a 12 minute drive to Middlebury where you can find shops, restaurants and Middlebury College. Burlington is about 40 minutes north of where we are located. Hiking/skiing in the Green Mountains, fly fishing in the nearby New Haven River, boating/swimming on Lake Champlain, and enjoying the many local craft breweries and wineries are some of the many activities you have access to from this beautiful spot.
4–11 MayIndividual Host,
£74 per night
4.99 out of 5 average rating, 237 reviews
Guest favourite
Farm stay in Cornwall
Cozy country guest house
Our guesthouse is nestled in the Lemon Faire River Valley. This 1 bedroom with kitchen, bathroom, and extra sleeping loft gives you a quiet experience of the Vermont countryside. The outside entry deck overlooks over a 1000 acres of open field and farmland. Middlebury is only 3 miles away and offers museums, restaurants, and shopping. This is an active farm: horses, dogs, geese, a duck, and chickens. Please read the house manual as it has lots more information about the house and property.
10–17 JanIndividual Host,
£166 per night
4.93 out of 5 average rating, 199 reviews
Guest favourite
Flat in Middlebury
Cozy Apt. Near heart of Middlebury Fiber WIFI
Enjoy a cozy, stylish and private experience at this centrally-located apartment. Free ultra fast Fiber Wifi, office desk and chair for work. 2, smart Tv’s connected to wifi for your enjoyment. Close to Middlebury College. Visit nearby hiking trails, Lake Dunmore, Branberry Beach and much more! Near Middlebury College Snow Bowl and Robert Frost Trails for beautiful nature views. Restaurants and shops within walking distance and a short drive or bike ride to downtown Middlebury.
3–10 MayIndividual Host,
£128 per night
4.86 out of 5 average rating, 133 reviews

Popular amenities for Middlebury holiday rentals

Stay near Middlebury's top sights

Fire & Ice53 locals recommend
Rosie's18 locals recommend
A&W6 locals recommend
Two Brothers Tavern64 locals recommend
Mister Up's Restaurant & Pub20 locals recommend
Middlebury College43 locals recommend

Other great holiday rentals in Middlebury

Guest favourite
Farm stay in Salisbury
Quaint 1-bedroom cottage on Blue Ledge Farm
17–24 AprIndividual Host,
£85 per night
4.95 out of 5 average rating, 258 reviews
Guest favourite
Cottage in New Haven
Hilltop Cottage With a View
5–12 NovIndividual Host,
£151 per night
4.99 out of 5 average rating, 145 reviews
Guest favourite
Flat in New Haven
Dog Team Falls Apartment - Minutes from Middlebury
9–16 SeptIndividual Host,
£145 per night
4.99 out of 5 average rating, 180 reviews
Guest favourite
Flat in Middlebury
The Barn at Middlebury
22–29 JulIndividual Host,
£484 per night
5.0 out of 5 average rating, 183 reviews
Guest favourite
Flat in Middlebury
Downtown 1 bedroom Apartment in Middlebury
31 Jul – 7 AugIndividual Host,
£178 per night
5.0 out of 5 average rating, 167 reviews
Guest favourite
Guest house in Middlebury
Middlebury cottage walk to campus.
21–28 NovIndividual Host,
£233 per night
4.96 out of 5 average rating, 112 reviews
Guest favourite
Flat in Bristol
"Dragonfly Apartment" Private Bristol Apartment
30 May – 6 JunIndividual Host,
£74 per night
4.87 out of 5 average rating, 279 reviews
Guest favourite
Flat in New Haven
Gracious two bedroom just minutes to Middlebury!
11–18 JulIndividual Host,
£207 per night
4.99 out of 5 average rating, 135 reviews
Guest favourite
Loft in New Haven
Sunrise over South Mountain
30 Mar – 6 AprIndividual Host,
£121 per night
4.98 out of 5 average rating, 238 reviews
Guest favourite
Cabin in Bristol
Colonel's Camp in Buck Haven
5–12 DecIndividual Host,
£120 per night
4.86 out of 5 average rating, 167 reviews
Guest favourite
Cabin in Leicester
Log Cabin Getaway near Middlebury and Green Mtns
16–23 DecIndividual Host,
£109 per night
4.98 out of 5 average rating, 701 reviews
Guest favourite
Home in Middlebury
Entire House in Middlebury - Walk Everywhere
12–19 MayIndividual Host,
£319 per night
4.9 out of 5 average rating, 147 reviews

Quick stats about holiday rentals in Middlebury

Total rentals

60 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

3.4K reviews

Nightly prices starting at

£55 before taxes and fees

Destinations to explore

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