Middlebury vacation rentals

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Top-rated vacation rentals in Middlebury

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

Guest favorite

Cottage in New Haven

4.99 out of 5 average rating, 239 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.

Jun 18 – 25

ﺩ.ﺇ283 per night
Guest favorite

Apartment 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.

Apr 28 – May 5

ﺩ.ﺇ382 per night
Guest favorite

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.

Apr 24 – May 1

ﺩ.ﺇ341 per night

Popular amenities for Middlebury vacation 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 vacation rentals in Middlebury

Guest favorite

Barn in Ripton

4.93 out of 5 average rating, 139 reviews

Spring Snow Ski Vermont Middlebury SnowBowl Rikert

Nov 5 – 12

ﺩ.ﺇ557 per night
Guest favorite

Yurt in New Haven

4.91 out of 5 average rating, 254 reviews

Song Bird Sangha Yurt

May 30 – Jun 6

ﺩ.ﺇ467 per night
Guest favorite

Cabin in Bristol

4.86 out of 5 average rating, 169 reviews

Colonel's Camp in Buck Haven

Dec 16 – 23

ﺩ.ﺇ459 per night
Guest favorite

Guest suite in Bristol

4.96 out of 5 average rating, 107 reviews

South Mountain Guest Suite

May 11 – 18

ﺩ.ﺇ468 per night
Guest favorite

Home in Middlebury

5.0 out of 5 average rating, 108 reviews

In the heart of Middlebury, a modern farmhouse

Mar 1 – 8

ﺩ.ﺇ1,383 per night
Guest favorite

Apartment in Hancock

4.95 out of 5 average rating, 144 reviews

Suite in the Green Mountains

Oct 30 – Nov 6

ﺩ.ﺇ344 per night
Guest favorite

Condo in Vergennes

4.97 out of 5 average rating, 172 reviews

Little Brick House Off Main (Apt. B)

Jun 11 – 18

ﺩ.ﺇ484 per night
Guest favorite

Guesthouse in Middlebury

4.96 out of 5 average rating, 112 reviews

Middlebury cottage walk to campus.

Mar 9 – 16

ﺩ.ﺇ968 per night
Guest favorite

Cabin in Bristol

4.95 out of 5 average rating, 103 reviews

Cozy Cabin on the River in Bristol

Mar 14 – 21

ﺩ.ﺇ641 per night
Guest favorite

Apartment in Vergennes

4.98 out of 5 average rating, 312 reviews

Downtown Vergennes Art House/Glass Studio

Oct 22 – 29

ﺩ.ﺇ440 per night
Guest favorite

Cottage in Lincoln

4.87 out of 5 average rating, 852 reviews

The Barn at North Orchard, Near Middlebury

Nov 11 – 18

ﺩ.ﺇ458 per night
Superhost

Apartment in Bristol

4.86 out of 5 average rating, 116 reviews

Overlook at the Office

Feb 19 – 26

ﺩ.ﺇ269 per night

Other great vacation rentals in Middlebury

Guest favorite

Home in Leicester

4.98 out of 5 average rating, 129 reviews

Luxurious Cottage Massage Therapy Studio On Site

Feb 16 – 23

ﺩ.ﺇ671 per night
Guest favorite

Cabin in Rochester

4.95 out of 5 average rating, 387 reviews

Black haus: a hip, cool house hidden in a forest.

Feb 23 – Mar 2

ﺩ.ﺇ512 per night
Guest favorite

Apartment in Middlebury

4.85 out of 5 average rating, 136 reviews

Cozy Apt. Near heart of Middlebury Fiber WIFI

Aug 11 – 18

ﺩ.ﺇ572 per night
Guest favorite

Cottage in Brandon

4.91 out of 5 average rating, 264 reviews

Henrietta’s Hideaway-Walk Downtown!

Jun 25 – Jul 2

ﺩ.ﺇ338 per night
Guest favorite

Apartment in New Haven

4.99 out of 5 average rating, 137 reviews

Gracious two bedroom just minutes to Middlebury!

Aug 25 – Sep 1

ﺩ.ﺇ827 per night
Guest favorite

Apartment in Middlebury

5.0 out of 5 average rating, 86 reviews

Bluebird Studio- Light filled and airy

Oct 23 – 30

ﺩ.ﺇ334 per night
Guest favorite

Loft in Middlebury

4.94 out of 5 average rating, 64 reviews

Cozy Studio Apt. Walk to College and Town!

Mar 1 – 8

ﺩ.ﺇ576 per night
Superhost

Guest suite in Ripton

4.82 out of 5 average rating, 71 reviews

Rustic cozy 2 room guest suite with kitchenette.

Jan 9 – 16

ﺩ.ﺇ294 per night
Superhost

Guesthouse in Middlebury

4.85 out of 5 average rating, 48 reviews

Private Downtown Middlebury Home Walk Everywhere

May 16 – 23

ﺩ.ﺇ516 per night
Guest favorite

Home in Middlebury

5.0 out of 5 average rating, 41 reviews

Downtown Middlebury Farmhouse

Aug 8 – 15

ﺩ.ﺇ1,048 per night
Guest favorite

Apartment in Cornwall

4.81 out of 5 average rating, 26 reviews

Beautiful 1-bedroom apt w/ stunning views

Aug 6 – 13

ﺩ.ﺇ631 per night
Guest favorite

Home in Middlebury

5.0 out of 5 average rating, 27 reviews

River House in the Heart of Middlebury

Apr 22 – 29

ﺩ.ﺇ1,170 per night

Quick stats about vacation 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

ﺩ.ﺇ257 before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Middlebury?

    Yes! Work meets play with ease at over 30 vacation rentals in Middlebury featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Middlebury?

    Four-legged friends are welcome in Middlebury. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Middlebury have wireless internet?

    Absolutely! We offer over 20 house rentals with wireless internet in Middlebury. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Middlebury have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Middlebury. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Middlebury?

    Middlebury has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Middlebury?

    Experience the best of Middlebury with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore

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