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

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.

Tiny Sparrow House,  Luxury & Charm In Middlebury - Middlebury, VT
10 16 reviews
Middlebury, VT
06/25 – 06/27
$1655/nighttotal: $3310 (2 )

Tiny Sparrow House, Luxury & Charm In Middlebury

1 2
apartment , Middlebury
This Middlebury house is located in downtown, within walking distance of Middlebury College and the downtown area. The house has excellent user, location, and cleanliness ratings. The home features four bedrooms and three and a half bathrooms, comfortably accommodating up to 8 guests. The house is fully equipped with all necessary amenities, including a kitchen with a fridge, microwave, and dishwasher, as well as a spacious backyard with a swing, gas grill, fire pit, and Adirondack chairs.
Green Mountain Village Getaway In Picturesque Bristol, Vermont. - Middlebury, VT
10 7 reviews
Middlebury, VT
07/18 – 08/01
$403/nighttotal: $5642 (14 )

Green Mountain Village Getaway In Picturesque Bristol, Vermont.

4 1
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.
The Barn At Middlebury - Middlebury, VT
10 213 reviews
Middlebury, VT
07/18 – 08/01
$623/nighttotal: $8722 (14 )

The Barn At Middlebury

1 1
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

Modern Woodland Escape W Wshr Dryer And Large Yard - Middlebury, VT
Middlebury, VT
07/18 – 08/01
$233/nighttotal: $3262 (14 )

Modern Woodland Escape W Wshr Dryer And Large Yard

1 1
house , Ripton
This Ripton vacation home, offering a 'Woodland Escape,' is located 22 miles from Mad River and conveniently situated 9.1 miles from Branbury State Park and 10 miles from Texas Falls Recreation Area.
This 1500 square foot house accommodates up to six guests with one bathroom, a full kitchen including a fridge and microwave oven, air conditioning, and on-site parking, plus a private entrance and an in-unit washer and dryer.
Middlebury Bungalow - Middlebury, VT
10 8 reviews
Middlebury, VT
06/25 – 06/27
$320/nighttotal: $640 (2 )

Middlebury Bungalow

1 2
apartment , Middlebury
This two-bedroom, two-bathroom condo is located in a quiet neighborhood near the woods, offering easy access to downtown Middlebury's dining and amenities, ski slopes, and the Trail Around Middlebury (TAM) for outdoor activities.
This centrally located rental comfortably sleeps four guests and includes amenities such as a full kitchen with a dishwasher, air conditioning, parking, and dedicated office space, with keypad entry for secure access.
Charming One Bedroom Just Minutes To Middlebury! - Middlebury, VT
10 183 reviews
Middlebury, VT
07/18 – 08/01
$179/nighttotal: $2506 (14 )

Charming One Bedroom Just Minutes To Middlebury!

1 1
apartment , New Haven
This New Haven apartment is located just minutes from Middlebury College and is close to popular Vermont ski resorts like Sugarbush and Killington, making it a great choice for families visiting students or those looking to explore the area. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
This cozy rental unit features one bedroom and one bathroom, comfortably accommodating up to three guests. The apartment is fully equipped with modern amenities, including a full kitchen, central heating and air conditioning, high-speed Wi-Fi, a 65-inch smart TV, and a shared laundry room, making it perfect for a comfortable stay.
Vermont Modern Farmhouse + 46 Acres + Spectacular - Middlebury, VT
10 4 reviews
Middlebury, VT
07/18 – 08/01
$472/nighttotal: $6608 (14 )

Vermont Modern Farmhouse + 46 Acres + Spectacular

3 1
apartment , New Haven
This spacious lower-level apartment rental in rural New Haven, Vermont, offers easy access to attractions like Lincoln Peak Vineyard and Vergennes Falls Park, nestled near the Champlain Valley.
The 1,590-square-foot unit features three bedrooms (queen, queen, twin), two bathrooms, a private terrace with countryside views, and amenities including a fully equipped kitchen, laundry, and parking; it comfortably accommodates five guests and is situated on a 46-acre property with a fire pit and access to hiking and other outdoor activities.

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.

Destinations nearby

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
Middlebury, VT
07/18 – 08/01
$315/nighttotal: $4410 (14 )

Tasteful Two Bedroom Just Minutes To Middlebury!

2 1
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.

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.

Tasteful Two Bedroom Just Minutes To Middlebury! - Middlebury, VT
10 108 reviews
Middlebury, VT
07/18 – 08/01
$289/nighttotal: $4046 (14 )

Tasteful Two Bedroom Just Minutes To Middlebury!

2 1
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.
Cider Mill Rd. Farmhouse - Middlebury, VT
Middlebury, VT
06/25 – 06/27
$801/nighttotal: $1602 (2 )

Cider Mill Rd. Farmhouse

1 2
apartment , Cornwall
This Cornwall, VT rental offers Green Mountain views and is located two miles from Middlebury College and downtown Middlebury.
This dog-friendly dwelling accommodates up to 8 guests with 2 bathrooms and a full kitchen featuring a microwave, dishwasher, and freezer, plus air conditioning and a garden.
Middlebury In-town Oasis - Middlebury, VT
9.3 28 reviews
Middlebury, VT
07/18 – 08/01
$259/nighttotal: $3626 (14 )

Middlebury In-town Oasis

1 1
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.
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