Middlebury vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Middlebury

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in New Haven

4.99 out of 5 average rating, 241 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

G$18,458 GYD per night

Guest favorite

Farm stay in Cornwall

4.93 out of 5 average rating, 201 reviews

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.

Jul 18 – 25

G$38,019 GYD per night

Guest favorite

Apartment in Middlebury

5.0 out of 5 average rating, 169 reviews

Downtown 1 bedroom Apartment in Middlebury

Beautifully renovated upstairs apartment in the heart of downtown Middlebury, adjacent to Middlebury College, across from the Otter Creek Bakery and the new Middlebury town park. This charming space occupies 800 square feet above an optometry office in a Greek Revival home originally built circa 1856. It provides plenty of privacy and is within walking distance to all the restaurants and downtown shopping. A queen bed in the bedroom, and a pull out couch in the living room accommodates 4.

May 11 – 18

G$45,949 GYD per night

Guest favorite

Apartment in Middlebury

5.0 out of 5 average rating, 184 reviews

The Barn at Middlebury

The Barn at Middlebury is within a 10 min. walk of the village center and 15 min to Middlebury College. The renovated barn is attached to the owners' residence. The separate guest quarters have a private entrance and include 3 newly renovated bedrooms, with two baths. The 1st floor bedroom has a Livingroom, kitchenette (Nespresso, microwave, Ref/Freezer, dishwasher, sink). Washer/Dryer. The 2 other 2nd Fl bedrooms share a large private bath. A terrace and screened porch is available.

Aug 20 – 27

G$112,640 GYD per night

Guest favorite

Cottage in New Haven

4.99 out of 5 average rating, 147 reviews

Hilltop Cottage With a View

Our newly built cozy and relaxing guest cottage is located in New Haven . It has stunning views and gorgeous sunsets!! Located just seven miles from Middlebury ,Vergennes and Bristol . All of which have great shops and restaurants! Close to many local attractions including ,Woodchuck Cider house, Lincoln Peak Vineyard, Ski areas, Hiking , rivers, lakes, restaurants and much more! Our goal was to provide guests with a home away from home! We feel our cottage offers that and much more.

Jan 23 – 30

G$33,512 GYD per night

Guest favorite

Yurt in New Haven

4.91 out of 5 average rating, 254 reviews

Song Bird Sangha Yurt

Songbird Sangha was thoughtfully created to provide a peaceful retreat from the world. It is nestled into a beautiful forest with privacy in mind. You will fall in love with the sky dome over your queen sized bed for the most comfortable star gazing ever! Your stay would not be complete without a complimentary campfire & marshmallow and if you would like more magic sign up for our Airbnb Experience The Healing Nature of Horses, a life enhancing encounter . Certified Wildlife Habitat.

Aug 30 – Sep 6

G$26,587 GYD per night

Guest favorite

Yurt in Bristol

4.93 out of 5 average rating, 235 reviews

Bristol Cozy Yurt near Skiing/Hiking|Maple Farm

Our cozy yurt is located within minutes of amazing, hiking, biking, swimming, skiing, breweries and much more! Sit around the campfire while listening to our resident owls or stare up at the stars through the dome. We're centrally located to some of the best hiking, biking and swimming in North Central Vermont. We're also close to civilization with several small towns within 15 minutes to explore for food, drink, art, and shopping. Or travel a bit further to Burlington..

Dec 2 – 9

G$22,444 GYD per night

Guest favorite

Condo in Vergennes

4.97 out of 5 average rating, 174 reviews

Little Brick House Off Main (Apt. B)

Bright, clean and cozy second-floor apartment located just steps to restaurants, bars, cafes, and shopping in the heart of historic downtown Vergennes. This convenient location is a 35-minute drive to Burlington and just 20 mins to Middlebury. A 10-minute drive to nearby Button Bay Park and Basin Harbor Resort on the shores of Lake Champlain. 35-minute drive to Mad River Glen Ski Area, 50-minute drive to Sugarbush Resort, and just 35 minutes to the Middlebury Snow Bowl.

May 31 – Jun 7

G$20,071 GYD per night

Guest favorite

Apartment in Middlebury

4.99 out of 5 average rating, 100 reviews

Mountain View Retreat

This clean, quiet, ground-level apartment enjoys an out-of-town feel and expansive mountain views while being conveniently located to the town of Middlebury, Middlebury College, the Green Mountain National Forest, the Middlebury College Snow Bowl and the Rikert Nordic Center, and more. This 1 bedroom/1 bath apartment features an open living concept and a fully equipped kitchen and is just 1.5 miles from restaurants and grocery stores and 2 miles from the college.

Jul 6 – 13

G$39,051 GYD per night

Guest favorite

Loft in New Haven

4.98 out of 5 average rating, 245 reviews

Sunrise over South Mountain

This is a spacious guesthouse/retreat where you can relax and unwind. There are great views and walking down the road is serene, with open fields bordered by woods and teaming with wildlife. In the winter you can Nordic ski or snowshoe right outside your door, through fields and woodland paths down by an active sugar-bush. We currently have chickens as well as my friendly dog Annie who loves to play. We also have a young kitty named LB who is a pip.

Jun 9 – 16

G$30,252 GYD per night

Guest favorite

Guest suite in Cornwall

4.99 out of 5 average rating, 126 reviews

Home Suite Home in Cornwall, Minutes from Midd!

Looking for a home away from home on your travels in the Champlain Valley? Whether you're searching for a place to lay your head while visiting your Middlebury College student, a home base while exploring the gorgeous Green Mountain State, or a secluded, peaceful retreat in which to write the next chapter of your book, we've got just the spot! Our home, with the private guest suite and deck, is situated perfectly for your Vermont holiday.

Sep 16 – 23

G$29,708 GYD per night

Guest favorite

Home in Middlebury

4.99 out of 5 average rating, 352 reviews

Nice one bedroom cottage

Located at the foot of the Green Mountains, a short walk to the Waybury Pub, nearby hiking, fishing and skiing. 4 miles to heart of Middlebury. Full kitchen, living room, bedroom(queen bed) and bathroom with stand up shower. ethernet connection/cable tv/washer-dryer/ac/ns

Jul 5 – 12

G$27,904 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Middlebury vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

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

Cabin in Bristol

4.86 out of 5 average rating, 172 reviews

Colonel's Camp in Buck Haven

Jan 21 – 28

G$25,372 GYD per night

Guest favorite

Apartment in Bristol

4.91 out of 5 average rating, 116 reviews

Peaceful Getaway in Bristol Village.

Jul 1 – 8

G$22,047 GYD per night

Guest favorite

Farm stay in Salisbury

4.95 out of 5 average rating, 267 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

Dec 17 – 24

G$27,368 GYD per night

Guest favorite

Home in Ripton

4.89 out of 5 average rating, 256 reviews

Cozy cottage near nature

May 10 – 17

G$28,634 GYD per night

Guest favorite

Cabin in Bristol

4.95 out of 5 average rating, 106 reviews

Cozy Cabin on the River in Bristol

Sep 10 – 17

G$35,842 GYD per night

Guest favorite

Apartment in Bristol

4.88 out of 5 average rating, 285 reviews

"Dragonfly Apartment" Private Bristol Apartment

Nov 13 – 20

G$18,772 GYD per night

Guest favorite

Apartment in Vergennes

4.98 out of 5 average rating, 314 reviews

Downtown Vergennes Art House/Glass Studio

Nov 26 – Dec 3

G$25,064 GYD per night

Guest favorite

Apartment in Hancock

4.95 out of 5 average rating, 146 reviews

Suite in the Green Mountains

Oct 10 – 17

G$19,567 GYD per night

Show all

Other great vacation rentals in Middlebury

Guest favorite

Cottage in Lincoln

4.87 out of 5 average rating, 856 reviews

The Barn at North Orchard, Near Middlebury

May 2 – 9

G$26,831 GYD per night

Superhost

Apartment in Bristol

4.86 out of 5 average rating, 117 reviews

Overlook at the Office

Sep 6 – 13

G$15,391 GYD per night

Guest favorite

Hut in Ripton

4.94 out of 5 average rating, 133 reviews

Skylight Hut-glamping near hiking, biking, fishing

Jun 14 – 21

G$17,340 GYD per night

Guest favorite

Cabin in Rochester

4.95 out of 5 average rating, 390 reviews

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

Dec 5 – 12

G$29,146 GYD per night

Guest favorite

Barn in Ripton

4.93 out of 5 average rating, 141 reviews

Green Mountains Vermont Middlebury Bread Loaf Barn

Oct 18 – 25

G$39,341 GYD per night

Guest favorite

Home in Goshen

4.82 out of 5 average rating, 249 reviews

Nature Lover's Paradise

Oct 19 – 26

G$28,411 GYD per night

Guest favorite

Guesthouse in Monkton

4.98 out of 5 average rating, 104 reviews

Beautiful, 1 BR guesthouse

Oct 24 – 31

G$33,983 GYD per night

Guest favorite

Apartment in Salisbury

4.89 out of 5 average rating, 143 reviews

Doc's Lake House 1st floor, 2 bdrm full apartment

Mar 29 – Apr 5

G$35,964 GYD per night

Show all

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
3.5K reviews
Nightly prices starting at
G$14,629 GYD 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 a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Middlebury. Enjoy a tailored experience with all the comforts you desire.
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 house rentals in Middlebury?
Experience the best of Middlebury with our house 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.
What are the most popular amenities for House Rentals in Middlebury?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 10 homes with a bbq area, over 20 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Middlebury vacation rentals

Top-rated vacation rentals in Middlebury

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Middlebury vacation rentals

Stay near Middlebury's top sights

Other great vacation rentals in Middlebury

Cabin in Bristol

Apartment in Bristol

Farm stay in Salisbury

Home in Ripton

Cabin in Bristol

Apartment in Bristol

Apartment in Vergennes

Apartment in Hancock

Other great vacation rentals in Middlebury

Cottage in Lincoln

Apartment in Bristol

Hut in Ripton

Cabin in Rochester

Barn in Ripton

Home in Goshen

Guesthouse in Monkton

Apartment in Salisbury

Quick stats about vacation rentals in Middlebury

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Middlebury?

Are there pet-friendly vacation rentals in Middlebury?

Do house rentals in Middlebury have a bbq area?

Do house rentals in Middlebury have wireless internet?

Do apartment rentals in Middlebury have air conditioning?

Are there family-friendly house rentals in Middlebury?

How much does it cost to stay in house rentals in Middlebury?

What are the most popular amenities for House Rentals in Middlebury?

Destinations to explore