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Middlebury, VT vacation rentals
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Best Vacation rentals and Airbnb offers in Middlebury, VT

Find Vacation Rentals in Downtown of Middlebury, VT

From vibrant downtown areas to historic streets, these Middlebury, VT vacation rentals put you close to everything worth seeing.

Walk Everywhere And Enjoy A Historic Vermont Home - Middlebury, VT
9.9 108 reviews

Walk Everywhere And Enjoy A Historic Vermont Home

apartment, Middlebury
This charming house is located in Middlebury, within walking distance of downtown shops and restaurants. This historic home has earned excellent ratings for location, cleanliness, and overall user experience.
The two-story home comfortably sleeps six guests and offers three bedrooms, a full kitchen, dining room, living room, and two bathrooms. Guests can enjoy modern comforts like air conditioning, a hot tub, and a backyard garden while soaking in the historic charm of original wood floors, tin ceilings, and doors.
Graduation, Skiing, Hiking - Best In Town Location - Middlebury, VT
9.7 66 reviews

Graduation, Skiing, Hiking - Best In Town Location

house, Middlebury
This Middlebury duplex is conveniently located downtown, within walking distance of Middlebury College, the Coop grocery store, and Royal Oak Coffee, offering easy access to shops and restaurants.
The two-bedroom, one-bathroom home sleeps three guests and features a full kitchen with modern appliances, complimentary breakfast items, and parking for two cars, plus proximity to Lake Dunmore and Killington ski resort.
Middlebury In-town Oasis - Middlebury, VT
9.1 30 reviews

Middlebury In-town Oasis

apartment, Middlebury
This Middlebury apartment rental is located near Middlebury College, within walking distance of the college and the town's shops and restaurants.
The 8-guest dwelling boasts an updated kitchen and bathrooms, a spacious patio with a firepit, BBQ grill, and wood-fired oven, plus classic wood floors throughout.
South Street Retreat
Walk To Campus/town - Middlebury, VT
10 24 reviews

South Street Retreat Walk To Campus/town

apartment, Middlebury
This 1895 home, a 3-bedroom, 2-bathroom rental, is situated within walking distance of downtown Middlebury, Middlebury College, and Porter Hospital, placing guests just 2,640 feet from local shops and cafes.
This accommodation for up to seven guests features a fully equipped kitchen, air conditioning, a garden with a firepit, and parking, with most of the home accessible for a convenient self-check-in experience.

Best Middlebury, VT vacation rentals with air conditioning

Middlebury Cottage Walk To Campus. - Middlebury, VT
9.9 145 reviews

Middlebury Cottage Walk To Campus.

house, Weybridge
This charming cottage is located in Weybridge, a short walk from Middlebury College's Bicentennial Hall and a 10-12 minute walk to the town center, offering a peaceful retreat with picturesque views of the river and landscaped grounds. The cottage consistently receives excellent ratings for its cleanliness, location, and overall experience.
This two-bedroom, one-bathroom home comfortably accommodates a family of four. Enjoy the fully equipped kitchenette, fireplace, Wi-Fi, air conditioning, and EV charger, as well as a private screened porch and a canoe for exploring the surrounding area.
Cheerful 1 Bedroom Cabin In Green Mtn Natl Forest - Middlebury, VT
No reviews

Cheerful 1 Bedroom Cabin In Green Mtn Natl Forest

apartment, Lincoln
This 2-bedroom apartment is located in Bristol, within the Green Mountain National Forest, offering convenient access to Sugarbush Ski Resort and Bristol Cliffs Wilderness.
This accommodation accommodates up to 4 guests and features internet, air conditioning, towels, soap, toilet paper, a hairdryer, a dryer, and an ironing board.
4-bedroom House On The Town Green In The Heart Of Charming Bridport, Vermont - Middlebury, VT
10 3 reviews

4-bedroom House On The Town Green In The Heart Of Charming Bridport, Vermont

apartment, Bridport
This Bridport rental house is located 12 miles from Chimney Point State Historic Site and 32 miles from Lake George, offering convenient access to local attractions.
This accommodation features 4 bedrooms and 2.5 bathrooms, accommodating up to 10 guests with amenities including air conditioning, a microwave, a dishwasher, and Wi-Fi.
Robert Frost Mountain Cabins - Middlebury, VT
10 41 reviews

Robert Frost Mountain Cabins

cabin, Ripton
This Ripton cabin is located in Middlebury, Vermont, just 20 miles from the Mad River and 13 miles from Branbury State Park and Texas Falls Recreation Area, offering a peaceful escape from the city while being close to nature. The cabin has received excellent ratings for its location, cleanliness, and overall experience.
The 2-bedroom, 1-bathroom cabin offers 650 square feet of space and can accommodate up to 6 guests. It includes amenities like a private hot tub, a fully equipped kitchen, a terrace, a garden, and free parking, making it perfect for families or groups looking to enjoy the outdoors and relax in comfort.

Frequently Asked Questions about vacation rentals in Middlebury, VT

  • Which walking or cycling routes are the best in Middlebury, VT?

    The Middlebury Greenway is a great option for walking or biking, offering a paved path along the Otter Creek. For a more challenging ride, try the scenic route along Route 125, which winds through the Green Mountains. If you're looking for a shorter walk, the Middlebury College campus has beautiful walking paths.
  • What are the best Airbnb and vacation rentals in Middlebury, VT?

    Centrally-located Victorian Carriage House, Middlebury Gem Open Concept And 5 Minutes From Town and The Barn At Middlebury are the most popular Airbnb and vacation rentals in Middlebury, VT among travelers.

  • What sports or outdoor activites can visitors enjoy in and around Middlebury, VT?

    Middlebury is a great place for outdoor enthusiasts! You can enjoy hiking, biking, and skiing in the Green Mountains. In the summer, you can go swimming, kayaking, or fishing on Lake Champlain. In the winter, you can try cross-country skiing or snowshoeing at the Middlebury Snow Bowl.
  • What are the most popular Airbnbs in Middlebury, VT?

  • What other towns or cities can be easily accessed from Middlebury, VT?

    Middlebury is conveniently located near several other towns and cities. You can easily drive to Burlington, the largest city in Vermont, which is about a 45-minute drive. Other nearby towns include Vergennes, a historic village on Lake Champlain, and Waterbury, known for its breweries and restaurants.
  • What are the best rentals for families and kids in Middlebury, VT?

    The best rentals for families and kids in Middlebury, VT are The Barn At Middlebury, Private Apartment In Middlebury and The Cottage Apartment In Downtown Middlebury.

  • What amenities are commonly available in vacation rentals in Middlebury, VT?

    Vacation rentals in Middlebury typically offer amenities like kitchens, laundry facilities, and Wi-Fi. Many also have fireplaces, decks, and hot tubs. You can find a wide range of vacation rentals, from cozy studios to spacious houses, to fit your needs and budget.
  • What time of year is best to rent a vacation rental Middlebury, VT?

    The best time to visit Middlebury depends on your interests. Summer is great for hiking, biking, and swimming, while fall offers beautiful foliage and cooler temperatures. Winter is perfect for skiing and snowshoeing. Spring brings blooming flowers and warmer weather.
  • What are the local dishes in Middlebury, VT region?

    Vermont is known for its maple syrup, so you'll find it in many local dishes. Try a classic Vermont pancake breakfast with maple syrup, or a Vermont cheddar cheese fondue. You can also find delicious local craft beers and wines.

Popular destinations

Guest-Favorite Vacation Rentals with a Terrace in Middlebury, VT

Wake up to breathtaking views at these Middlebury, VT vacation rentals with balconies, perfect for your morning coffee.

Tasteful Two Bedroom Just Minutes To Middlebury! - Middlebury, VT
No reviews

Tasteful Two Bedroom Just Minutes To Middlebury!

apartment, New Haven
This recently renovated 2-bedroom apartment in New Haven, Vermont, is situated on a 25-acre estate, located 4 miles north of Middlebury and 28 miles south of Burlington.
This accommodation offers a private country setting with a balcony overlooking an apple orchard, a gourmet kitchen, fast WiFi, and shared access to a fire ring and grill area, with nearby recreational opportunities including hiking and skiing.
Purple Door Cottage In The Heart Of Middlebury! - Middlebury, VT
No reviews

Purple Door Cottage In The Heart Of Middlebury!

apartment, Middlebury
This 2-bedroom, 2-bathroom apartment in Middlebury offers central pedestrian access, located steps from Fire & Ice restaurant and one block from the town green, with Middlebury College and the train station within easy walking distance.
This 1500 sq ft residence comfortably sleeps six, featuring a king bedroom, a guest room with multiple beds, a queen sleeper sofa, a Great Room with a remote work area, a fully appointed kitchen, and a spacious deck with a grill and fire ring, all equipped with 1200 Mbps WiFi.
Beautiful Timber Frame Just Minutes To Middlebury! - Middlebury, VT
10 1 review

Beautiful Timber Frame Just Minutes To Middlebury!

apartment, New Haven
This 5010 sq ft New Haven apartment is located on 25 private acres with mountain views, offering 6 bedrooms and 4 bathrooms for up to 12 guests, just a 5-minute drive from Middlebury's amenities and near recreational spots like swimming holes and hiking trails. This estate features post and beam construction, a solarium, a finished basement with a theater area, central heating and air conditioning, super-fast WiFi, a tennis court, and ample parking with an enormous fire ring.

Choose the Right Family-Friendly Vacation Rentals in Middlebury, VT

Ideal for family vacations, these Middlebury, VT rentals or Airbnbs offer spacious layouts near top city attractions.

Close To College-cheerful, Quiet, 2 Bedroom Home - Middlebury, VT
10 127 reviews

Close To College-cheerful, Quiet, 2 Bedroom Home

apartment, Weybridge
This apartment is located in Middlebury, just a short 1.5-mile drive from Middlebury College, offering a quiet residential setting close to the town's attractions. Guests consistently rate the apartment excellent for location, cleanliness, and overall experience.
The apartment features one bathroom and comfortably accommodates up to four guests. Amenities include a fully equipped kitchen, air conditioning, a private garden, parking, and high-speed internet, making it ideal for families or groups looking for a convenient and comfortable stay.
Gracious Two Bedroom Just Minutes To Middlebury! - Middlebury, VT
10 245 reviews

Gracious Two Bedroom Just Minutes To Middlebury!

apartment, New Haven
This second-story apartment is situated on a 25-acre estate just north of Middlebury, offering easy access to the village (minutes away) and Burlington (within 30 minutes). It offers beautiful mountain views and sunsets over the Adirondacks and Green Mountains.
The apartment has excellent user, location, and cleanliness ratings. It has 2 bedrooms with brand-new queen beds and 1 bathroom. It can accommodate up to 6 guests. It features a gourmet kitchen with granite countertops and stainless steel appliances, a spacious great room with a 65" smart TV and cozy seating, and super-fast free Wi-Fi. Pets are allowed upon permission and with an additional fee.
Updated Apartment Downtown - Middlebury, VT
10 42 reviews

Updated Apartment Downtown

apartment, Middlebury
This Middlebury apartment rental is conveniently located within walking distance of downtown Middlebury and Middlebury College.
The recently renovated two-bedroom unit sleeps three guests and features a full kitchen with a dishwasher, microwave, and refrigerator, plus high-quality bedding and linens; uncovered parking is available on-site.
The Barn At Middlebury - Middlebury, VT
10 213 reviews

The Barn At Middlebury

apartment, Middlebury
This charming apartment is located just a 10-minute walk from Middlebury's village center and a 15-minute walk from Middlebury College, offering a peaceful retreat in a renovated barn. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience.
This rental offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a private entrance, dedicated parking, a private terrace and screened porch with a fireplace, modern appliances, and a washer/dryer.

Best Middlebury, VT vacation rentals with parking

Gracious Two Bedroom Just Minutes To Middlebury! - Middlebury, VT
No reviews

Gracious Two Bedroom Just Minutes To Middlebury!

apartment, New Haven
Charming Farmhouse At Sunrise Orchards - Middlebury, VT
9.9 49 reviews

Charming Farmhouse At Sunrise Orchards

gîte, Cornwall
Cozy Apartment  Minutes To Middlebury - Middlebury, VT
9.7 215 reviews

Cozy Apartment Minutes To Middlebury

apartment, Middlebury
Vt Country Cottage - Middlebury, VT
10 20 reviews

Vt Country Cottage

apartment, Middlebury

Our Favorite 5-Star Vacation Rentals in Middlebury, VT

Elevate your stay in a luxury vacation rental or Airbnb in Middlebury, VT, featuring high-end finishes and a prime location.

Purple Door Cottage In The Heart Of Middlebury! - Middlebury, VT
No reviews

Purple Door Cottage In The Heart Of Middlebury!

house, Middlebury

Top-Rated Pet-Friendly Vacation Rentals in Middlebury, VT

Travel with ease to Middlebury, VT with pet-friendly rentals located near local dog parks and scenic city walks.

Comfort And Privacy With A View On The Farm - Middlebury, VT
No reviews

Comfort And Privacy With A View On The Farm

house, Cornwall
New England Chalet  Champlain Valley - Middlebury, VT
10 1 review

New England Chalet Champlain Valley

apartment, Middlebury
Middlebury Carriage House - Middlebury, VT
9.8 12 reviews

Middlebury Carriage House

apartment, Middlebury
Historic Farmhouse In Middlebury - Middlebury, VT
9.8 160 reviews

Historic Farmhouse In Middlebury

house, Middlebury

Search Vacation Rentals with Swimming Pool in Middlebury, VT

A Middlebury, VT vacation rental with a pool ensures a refreshing swim in the heart of the city is always an option.

Tasteful Two Bedroom Just Minutes To Middlebury! - Middlebury, VT
No reviews

Tasteful Two Bedroom Just Minutes To Middlebury!

apartment, New Haven

Explore Vacation Rentals with Jacuzzi in Middlebury, VT

Unwind after a day of urban exploration with a private hot tub at your own vacation rental in Middlebury, VT.

Scandi Vermont Retreat - Middlebury, VT
10 4 reviews

Scandi Vermont Retreat

apartment, Middlebury
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