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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.

Modern Apartment 2 In Middlebury - Middlebury, VT
9.8 33 reviews

Modern Apartment 2 In Middlebury

apartment, Middlebury
This three-bedroom Middlebury apartment is located in Downtown Middlebury, within walking distance of Middlebury College and local shops and restaurants.
The recently renovated rental features a full kitchen with a fridge, freezer, and microwave, sleeps six guests in one queen, one full, and two twin beds, and offers nearby public parking.
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.
In The Heart Of Middlebury, A Modern Farmhouse - Middlebury, VT
10 171 reviews

In The Heart Of Middlebury, A Modern Farmhouse

apartment, Middlebury
This Middlebury rental is located on South Street, just a short walk from both Middlebury College and the town center. It has received excellent ratings for location, cleanliness, and overall experience.
This 3-bedroom home can accommodate up to 6 guests and features a fully equipped kitchen, a comfortable living area with a large TV, and a relaxing side porch. You'll also enjoy modern amenities like high-speed internet, air conditioning, and a private driveway with parking for two cars.
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

Tasteful Two Bedroom Just Minutes To Middlebury! - Middlebury, VT
10 116 reviews

Tasteful Two Bedroom Just Minutes To Middlebury!

apartment, New Haven
This apartment is located on a 25-acre estate, just four miles north of Middlebury and 28 miles south of Burlington, offering a peaceful retreat amidst the natural beauty of Vermont. Guests consistently rate this rental as excellent for its cleanliness, location, and overall experience. The apartment offers a spacious and serene setting, accommodating up to four guests. The fully equipped kitchen, private balcony, and access to a shared fire ring and outdoor grill make this apartment a perfect choice for travelers seeking a comfortable and relaxing stay.
Green Mountain Village Getaway In Picturesque Bristol, Vermont. - Middlebury, VT
9.8 9 reviews

Green Mountain Village Getaway In Picturesque Bristol, Vermont.

apartment, Bristol
This Bristol mountain home, a short 10-minute walk from Lawrence Memorial Library and Holley Hall, offers easy access to Bristol Cliffs Wilderness and Green Mountain National Forest within a 15-minute drive.
This four-bedroom, two-bathroom vacation rental sleeps eight, boasting a fully equipped kitchen, Wi-Fi, a terrace, a garden, a tennis court, and parking; barbecue grills are available for outdoor cooking.
Midd Manor - Middlebury, VT
9.9 23 reviews

Midd Manor

apartment, Middlebury
This Middlebury, Vermont apartment is conveniently located within walking distance of downtown, minutes from the TAM trails, and a 45-50 minute drive from Killington and Sugarbush ski resorts.
The one-bedroom, one-bathroom unit sleeps two guests and features a kitchen, air conditioning, parking, and internet access; nearby attractions include Fire and Ice, 2 Brothers Tavern, American Flatbread, and the Middlebury Natural Foods Co-op.
Beautiful 4-bedroom Home Beside Middlebury College - Middlebury, VT
9.6 67 reviews

Beautiful 4-bedroom Home Beside Middlebury College

apartment, Middlebury
This vacation home is located in Middlebury, just a short walk from Middlebury College, the arts center, and the Vermont Folklife Center, making it a convenient base for exploring the town's cultural offerings. It has received excellent reviews from previous guests, making it a popular choice for travelers.
The house has 4 bedrooms and 3 bathrooms, making it comfortable for groups of up to 10 people. You'll find a fully equipped kitchen, a spacious garden, a terrace, a spa, and parking, providing everything you need for a relaxing and enjoyable stay.

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.
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.
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.
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.
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.
Vt Getaway Near Middlebury & Lake Dunmore - Middlebury, VT
9.9 162 reviews

Vt Getaway Near Middlebury & Lake Dunmore

house, Salisbury
This studio apartment is conveniently located near Middlebury, Vermont, just a short drive from Lake Dunmore, Brandon, Rikert Outdoor Center, and Snowbowl, offering easy access to outdoor activities and local attractions. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment comfortably accommodates three guests and features a well-equipped kitchenette, a spacious living area with natural light, and a patio with scenic views. The apartment also includes amenities like air conditioning, a garden, parking, and internet access, making it a perfect choice for travelers seeking a comfortable and convenient stay in the area.

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

Middlebury Cottage Walk To Campus.

house, Weybridge
Cornwall 1820 Farmhouse - Middlebury, VT
10 11 reviews

Cornwall 1820 Farmhouse

apartment, Cornwall
Cheerful 1 Bedroom Cabin In Green Mtn Natl Forest - Middlebury, VT
No reviews

Cheerful 1 Bedroom Cabin In Green Mtn Natl Forest

apartment, Lincoln

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.

Cozy House 4 Bedroom 3 Bath With Mountain Views - Middlebury, VT
10 50 reviews

Cozy House 4 Bedroom 3 Bath With Mountain Views

apartment, Cornwall

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.

Historic Farmhouse In Middlebury - Middlebury, VT
9.8 160 reviews

Historic Farmhouse In Middlebury

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

Middlebury Carriage House

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

New England Chalet Champlain Valley

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

Comfort And Privacy With A View On The Farm

house, Cornwall

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.

Cider Mill Rd. Farmhouse - Middlebury, VT
9.3 3 reviews

Cider Mill Rd. Farmhouse

apartment, Cornwall

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.

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

Walk Everywhere And Enjoy A Historic Vermont Home

apartment, Middlebury
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