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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.

Miss Dee's Retreat - Middlebury, VT
9.9 95 reviews
Middlebury, VT
08/01 – 09/30
$97/nighttotal: $5820 (60 )

Miss Dee's Retreat

1 2
house , Salisbury
This peaceful garage apartment is located in a tranquil wooded environment, a short drive from Salisbury's attractions.
This accommodation offers a queen-sized bed and a sleeper chair accommodating up to three guests, with amenities including a full kitchen, WiFi, yoga mat, and fresh eggs from the host's hens.
Close To College-cheerful, Quiet, 2 Bedroom Home - Middlebury, VT
10 122 reviews
Middlebury, VT
06/25 – 06/27
$300/nighttotal: $600 (2 )

Close To College-cheerful, Quiet, 2 Bedroom Home

1 2
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.
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.
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.

Best Middlebury, VT vacation rentals with parking

Lincoln Escape - Middlebury, VT
9.5 74 reviews
Middlebury, VT
08/01 – 09/30
$472/nighttotal: $28320 (60 )

Lincoln Escape

3 2
house , Lincoln
Lincoln Escape, a three-bedroom Vermont home, is located 8.6 miles from Chimney Point State Historic Site and 14 miles from the Mad River.
This 2960-square-foot vacation rental boasts three bathrooms, a fully equipped kitchen with dishwasher, a patio, garden, fireplace, free Wi-Fi, and on-site parking, comfortably accommodating families or groups.
Country Getaway - Middlebury, VT
9.4 32 reviews
Middlebury, VT
08/01 – 09/30
$186/nighttotal: $11160 (60 )

Country Getaway

1 2
apartment , Cornwall
This accommodation is located in Addison County, Vermont, 7 miles from Middlebury and offers scenic views of the countryside. It has very good user and location ratings and excellent cleanliness ratings. The accommodation has 3 bedrooms, 1 bathroom, and can accommodate up to 6 guests. It features a kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, internet, and a spacious outdoor deck.
Guests can enjoy the tranquil rural setting with wildlife sightings, and proximity to Middlebury College. The accommodation also offers an unfenced yard, abundant natural light, well-equipped kitchen and laundry facilities, and no cable television.
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.
Bluebird Studio-
Light Filled And Airy - Middlebury, VT
10 182 reviews
Middlebury, VT
06/25 – 06/27
$174/nighttotal: $348 (2 )

Bluebird Studio- Light Filled And Airy

1 2
apartment , Middlebury
This Middlebury studio apartment is located just over a mile from downtown Middlebury's shops and restaurants, offering a peaceful retreat while remaining conveniently close to town attractions.
The 550-square-foot private unit features a queen-size bed, separate dressing room, fully equipped kitchen with fridge and microwave, air conditioning, and access to a large backyard and covered outdoor space; it comfortably sleeps four guests.

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.

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.
Easy Access To Middlebury - Middlebury, VT
Middlebury, VT
08/01 – 09/30
$202/nighttotal: $12120 (60 )

Easy Access To Middlebury

1 2
apartment , Middlebury
This 2-bedroom, 1-bathroom rental unit in Middlebury offers a peaceful and central location, under 5 minutes by car or a short walk to Middlebury College and the town center, accessible via the Trail Around Middlebury (TAM). This pet-friendly apartment accommodates up to 4 guests and includes internet, a kitchen, and air conditioning, with a fitness center available on-site.
Private Cozy Apartment • Near Middlebury - Middlebury, VT
9.9 90 reviews
Middlebury, VT
08/01 – 09/30
$140/nighttotal: $8400 (60 )

Private Cozy Apartment • Near Middlebury

1 2
apartment , Middlebury
This charming apartment is located in Middlebury, just a short walk from the town center and its many shops, restaurants, and attractions. Guests have consistently praised the apartment's excellent location, cleanliness, and overall experience.
The apartment features a modern and stylish design, comfortably accommodating up to three guests. Enjoy amenities like a fully equipped kitchen, fast internet, and air conditioning for a relaxing and enjoyable stay.
Forest Getaway - Middlebury, VT
Middlebury, VT
08/01 – 09/30
$420/nighttotal: $25200 (60 )

Forest Getaway

1 2
apartment , New Haven
This secluded woodland retreat is located 5 miles from Middlebury and Bristol, offering a tranquil Vermont experience.
This pet-friendly apartment accommodates up to 8 guests with 3 bathrooms, a full kitchen, and air conditioning, providing easy access to Lake Champlain and nearby state parks for hiking and skiing.
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