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.

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Guest favorite

Cottage in New Haven

4.99 out of 5 average rating, 246 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.

Guest favorite

Apartment in Bristol

4.91 out of 5 average rating, 120 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.

Guest favorite

Farm stay in Cornwall

4.93 out of 5 average rating, 204 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.

Guest favorite

Apartment in Middlebury

5.0 out of 5 average rating, 171 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.

Guest favorite

Apartment in Middlebury

5.0 out of 5 average rating, 186 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.

Guest favorite

Cottage in New Haven

4.99 out of 5 average rating, 148 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.

Guest favorite

Yurt in New Haven

4.91 out of 5 average rating, 256 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.

Guest favorite

Yurt in Bristol

4.92 out of 5 average rating, 240 reviews

Bristol Cozy Yurt near Hiking/Swimming|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..

Guest favorite

Cabin in Bristol

4.96 out of 5 average rating, 113 reviews

Cozy Cabin on the River in Bristol

Come experience true tranquility in this vintage and cute riverside cabin. The calming babble of the rocky New Haven River is the perfect soundtrack for you to relax, play, and explore. The small cabin has a deck and plenty of outdoor space with a picnic bench and fire pit. Feels remote but just a two minute drive to charming downtown Bristol featuring great restaurants, bars and shopping. Outdoorsy people will love all the swimming and hiking in the area as well!

Guest favorite

Apartment in Middlebury

4.99 out of 5 average rating, 104 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.

Guest favorite

Guest suite in Cornwall

4.99 out of 5 average rating, 128 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.

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

Farm stay in Salisbury

4.95 out of 5 average rating, 276 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

Guest favorite

Apartment in Vergennes

4.98 out of 5 average rating, 315 reviews

Downtown Vergennes Art House/Glass Studio

Guest favorite

Apartment in Bristol

4.88 out of 5 average rating, 286 reviews

"Dragonfly Apartment" Private Bristol Apartment

Guest favorite

Apartment in Hancock

4.95 out of 5 average rating, 146 reviews

Suite in the Green Mountains

Guest favorite

Barn in Ripton

4.93 out of 5 average rating, 146 reviews

Vermont Mountain Getaway Near Middlebury BreadLoaf

Guest favorite

Home in Leicester

4.98 out of 5 average rating, 137 reviews

Luxurious Cottage Massage Therapy Studio On Site

Guest favorite

Hut in Ripton

4.94 out of 5 average rating, 135 reviews

Skylight Hut-glamping near hiking, biking, fishing

Guest favorite

Loft in New Haven

4.98 out of 5 average rating, 248 reviews

Sunrise over South Mountain

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Other great vacation rentals in Middlebury

Guest favorite

Cabin in Rochester

4.95 out of 5 average rating, 397 reviews

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

Guest favorite

Guest suite in Hinesburg

4.96 out of 5 average rating, 1122 reviews

Boston Magazine Pick! Barn Loft

Superhost

Apartment in Bristol

4.85 out of 5 average rating, 121 reviews

Overlook at the Office

Guest favorite

Cottage in Lincoln

4.87 out of 5 average rating, 858 reviews

The Barn at North Orchard, Near Middlebury

Guest favorite

Guesthouse in Middlebury

4.97 out of 5 average rating, 116 reviews

Middlebury cottage walk to campus.

Guest favorite

Cabin in Vershire

4.99 out of 5 average rating, 192 reviews

Comfortable cozy cabin in the hills of Vermont!

Guest favorite

Guesthouse in Hinesburg

4.97 out of 5 average rating, 112 reviews

Cozy cottage in peaceful location

Guest favorite

Home in Middlebury

4.9 out of 5 average rating, 153 reviews

Entire House in Middlebury - Walk Everywhere

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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
$70 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 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.

Middlebury vacation rentals

Top-rated vacation rentals in Middlebury

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Middlebury vacation rentals

Stay near Middlebury's top sights

Other great vacation rentals in Middlebury

Farm stay in Salisbury

Apartment in Vergennes

Apartment in Bristol

Apartment in Hancock

Barn in Ripton

Home in Leicester

Hut in Ripton

Loft in New Haven

Other great vacation rentals in Middlebury

Cabin in Rochester

Guest suite in Hinesburg

Apartment in Bristol

Cottage in Lincoln

Guesthouse in Middlebury

Cabin in Vershire

Guesthouse in Hinesburg

Home in Middlebury

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 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?

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