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

4.99 out of 5 average rating, 238 reviews

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.

18–25 Jun

₹6,428 per night
Guest favourite

Flat in Bristol

4.91 out of 5 average rating, 116 reviews

Peaceful Getaway in Bristol Village.

Simple beauty, generous space and peace, in a second floor one bedroom guest apartment with bathtub, shower and galley kitchen without stove. Double futon in living area for additional guests. A very sweet private getaway for a couple, or group of friends or small family. Bristol is a true New England find with an active arts community, good restaurants and shops, as well as several yoga and tai chi instructional groups. Settle your energy here and enjoy life. Skiing and hiking nearby.

28 Apr – 5 May

₹8,659 per night
Guest favourite

Farm stay in Salisbury

4.95 out of 5 average rating, 263 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

This adorable cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

24 Apr – 1 May

₹7,734 per night

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

Barn in Ripton

4.93 out of 5 average rating, 139 reviews

Spring Snow Ski Vermont Middlebury SnowBowl Rikert

5–12 Nov

₹12,647 per night
Guest favourite

Cabin in Bristol

4.86 out of 5 average rating, 169 reviews

Colonel's Camp in Buck Haven

16–23 Dec

₹10,409 per night
Guest favourite

Yurt in New Haven

4.91 out of 5 average rating, 254 reviews

Song Bird Sangha Yurt

30 May – 6 Jun

₹10,603 per night
Guest favourite

Guest suite in Bristol

4.96 out of 5 average rating, 107 reviews

South Mountain Guest Suite

11–18 May

₹10,632 per night
Guest favourite

Home in Middlebury

5.0 out of 5 average rating, 108 reviews

In the heart of Middlebury, a modern farmhouse

16–23 May

₹25,354 per night
Guest favourite

Flat in Hancock

4.95 out of 5 average rating, 144 reviews

Suite in the Green Mountains

30 Oct – 6 Nov

₹7,804 per night
Guest favourite

Apartment in Vergennes

4.97 out of 5 average rating, 172 reviews

Little Brick House Off Main (Apt. B)

11–18 Jun

₹10,991 per night
Guest favourite

Guest house in Middlebury

4.96 out of 5 average rating, 112 reviews

Middlebury cottage walk to campus.

10–17 Mar

₹21,960 per night
Guest favourite

Flat in Vergennes

4.98 out of 5 average rating, 312 reviews

Downtown Vergennes Art House/Glass Studio

22–29 Oct

₹9,996 per night
Guest favourite

Cottage in Lincoln

4.87 out of 5 average rating, 852 reviews

The Barn at North Orchard, Near Middlebury

11–18 Nov

₹10,395 per night
Guest favourite

Cabin in Bristol

4.95 out of 5 average rating, 103 reviews

Cozy Cabin on the River in Bristol

14–21 Mar

₹14,552 per night
Guest favourite

Home in Middlebury

4.9 out of 5 average rating, 148 reviews

Entire House in Middlebury - Walk Everywhere

28 Apr – 5 May

₹29,977 per night

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

3.4T reviews

Nightly prices starting at

₹5,834 before taxes and fees

Destinations to explore

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