Holiday Rentals in Middlebury, VT

31 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Middlebury, VT holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Middlebury, VT

Best family friendly Middlebury, VT holiday rentals

Among the 31 accommodations in Middlebury, VT, here are the 4 best family friendly rentals

Close To College-cheerful, Quiet, 2 Bedroom Home - Middlebury, VT
10 122 reviews
Middlebury, VT
25/06 – 27/06
SG$386/nightTotal: SG$772 (2 )

Close To College-cheerful, Quiet, 2 Bedroom Home

1 2
apartment , Weybridge
This recently renovated apartment is located just 2.4 kilometres from Middlebury College in Middlebury, Vermont, a charming town with shops, restaurants and cultural attractions. The apartment enjoys excellent ratings for location, cleanliness and user experience.
The apartment is comfortably furnished and can accommodate up to 4 guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a garden and parking, making it a great choice for families and groups.
The Barn At Middlebury - Middlebury, VT
10 212 reviews
Middlebury, VT
18/07 – 01/08
SG$801/nightTotal: SG$11214 (14 )

The Barn At Middlebury

1 1
apartment , Middlebury
This charming, renovated barn conversion is situated just outside Middlebury's village centre, a 1.6km walk from the town and a 2.4km walk from Middlebury College. The property has received excellent ratings for location, cleanliness, and overall experience.
This self-catering property offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. The apartment is fully equipped with modern amenities, including a dishwasher, washer/dryer, and a Nespresso coffee machine, and boasts a private terrace, a screened porch with a fireplace, and a private entrance with parking for up to three vehicles.
Modern Farmhouse Steps To Middlebury College - Middlebury, VT
10 3 reviews
Middlebury, VT
18/07 – 01/08
SG$1742/nightTotal: SG$24388 (14 )

Modern Farmhouse Steps To Middlebury College

1 1
apartment , Middlebury
This centrally located flat in Middlebury offers prime downtown access, placing it within 500 meters of Main Street's shops and restaurants, 800 meters from Middlebury College, and a short walk to the Middlebury Museum of Art and Otter Creek.
This four-bedroom, three-bathroom residence accommodates up to 10 guests, featuring a fully equipped kitchen with a freezer, microwave, and dishwasher, air conditioning, a garden, fitness centre, and parking, making it ideal for exploring the town and attending events at the Town Hall Theater.
Walk Everywhere And Enjoy A Historic Vermont Home - Middlebury, VT
9.9 104 reviews
Middlebury, VT
25/06 – 27/06
SG$766/nightTotal: SG$1532 (2 )

Walk Everywhere And Enjoy A Historic Vermont Home

4 2
apartment , Middlebury
This charming house is situated in Middlebury, just a short walk from the town centre, offering easy access to shops, restaurants, and local attractions. It has received excellent ratings for its location, cleanliness, and overall experience.
The house has three bedrooms and one bathroom, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a relaxing garden, and a hot tub for added comfort.

Best Middlebury, VT holiday rentals with parking

Green Mountain Village Getaway In Picturesque Bristol, Vermont. - Middlebury, VT
10 7 reviews
Middlebury, VT
18/07 – 01/08
SG$518/nightTotal: SG$7252 (14 )

Green Mountain Village Getaway In Picturesque Bristol, Vermont.

4 1
apartment , Bristol
This four-bedroom house near Bristol, Vermont, is a short 1.6km walk from Lawrence Memorial Library and Holley Hall, and within a 2.4km radius of Bristol Cliffs Wilderness and Green Mountain National Forest.
This family-friendly dwelling boasts a fully equipped kitchen, Wi-Fi, a terrace, garden, tennis court, parking, and sleeps eight guests, with added amenities including barbecue grills and a sofa bed; enjoy stunning mountain views and tranquil surroundings.
Country Getaway - Middlebury, VT
9.4 32 reviews
Middlebury, VT
01/08 – 30/09
SG$239/nightTotal: SG$14340 (60 )

Country Getaway

1 2
apartment , Cornwall
This Cornwall holiday home is situated 11.3km from Middlebury, offering stunning countryside views.
Sleeping six guests, this three-bedroom property boasts a fully equipped kitchen with dishwasher, Wi-Fi, air conditioning, and a deck, plus a washing machine and dryer (restrictions apply).
Charming One Bedroom Just Minutes To Middlebury! - Middlebury, VT
10 183 reviews
Middlebury, VT
18/07 – 01/08
SG$230/nightTotal: SG$3220 (14 )

Charming One Bedroom Just Minutes To Middlebury!

1 1
apartment , New Haven
This one-bedroom flat is located just a short distance from Middlebury College, making it ideal for parents visiting their children or anyone wanting to explore the college town. It has received excellent ratings for location, cleanliness, and overall user experience.
The self-catering apartment is spacious enough to comfortably accommodate up to three guests. It includes a fully equipped kitchen, a bathroom with a bath and shower, a living area with dining space, and a 65-inch smart TV. You can also enjoy access to laundry facilities, a garden, and parking, and your furry friend is welcome too.
Middlebury In-town Oasis - Middlebury, VT
9.3 28 reviews
Middlebury, VT
25/06 – 27/06
SG$473/nightTotal: SG$946 (2 )

Middlebury In-town Oasis

1 2
apartment , Middlebury
This Middlebury apartment is conveniently located near Middlebury College, offering easy walking access to campus and the town centre.
Sleeping up to eight guests, the property boasts a spacious patio with a firepit, barbecue, and wood-fired oven, alongside an updated kitchen and bathrooms, classic wood floors, and ample parking.

Frequently asked questions about holiday rentals in Middlebury, VT

  • What are some interesting places to visit in or near Middlebury, VT?

    Middlebury is packed with things to see! You've got the charming downtown, the historic Middlebury College campus, and the stunning views from the top of Chipman Hill. A short drive away, you can explore the Shelburne Museum, the Vermont Teddy Bear Company, and the beautiful Lake Champlain.
  • What are the best Airbnb and vacation rentals in Middlebury, VT?

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

    The Greenway is a lovely paved path for walking or cycling, running along the Otter Creek. For a longer ride, try the scenic Route 7, which offers stunning views of the Green Mountains. And if you're up for a challenge, the climb up to the top of Chipman Hill is a must-do!
  • What are the most popular Airbnbs in Middlebury, VT?

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

    Middlebury is a haven for outdoor enthusiasts. You can go hiking in the Green Mountains, kayaking on Lake Champlain, skiing at Snow Bowl in the winter, and even play a round of golf at the Middlebury Golf Course.
  • 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 other towns or cities can be easily accessed from Middlebury, VT?

    Middlebury is a great base for exploring the surrounding area. You can easily reach Burlington, Vermont's largest city, in about an hour by car. And if you want to head to the coast, it's only a couple of hours to Portland, Maine.
  • What are the best rentals or Airbnbs with a jacuzzi in Middlebury, VT?

    The best vacation rental or Airbnb with a jacuzzi in Middlebury, VT is Middlebury - Vt Newly Renovated Four Bedroom Luxury Home (Sleeps 8).

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

    Vacation rentals in Middlebury typically offer all the comforts of home, including kitchens, laundry facilities, and Wi-Fi. Many also have fireplaces, hot tubs, and private decks or patios.
  • 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 outdoor activities, autumn is beautiful for foliage, and winter is perfect for skiing. Spring is a bit quieter, but the scenery is still lovely.
  • What are the local dishes in Middlebury, VT region?

    Vermont is famous for its maple syrup, so you'll find it in many dishes. Try the Vermont cheddar cheese, which is made locally. And don't forget to sample the local craft beers and wines!

Destinations nearby

Best Middlebury, VT holiday rentals with a balcony

Tasteful Two Bedroom Just Minutes To Middlebury! - Middlebury, VT
Middlebury, VT
18/07 – 01/08
SG$404/nightTotal: SG$5656 (14 )

Tasteful Two Bedroom Just Minutes To Middlebury!

2 1
apartment , New Haven
This recently renovated two-bedroom flat in New Haven, Vermont, is situated on a 25-acre estate, 6.5 kilometres north of Middlebury and 45 kilometres south of Burlington, offering a tranquil setting between the Green Mountains and Adirondack Mountains.
This pet-friendly accommodation for four guests features a gourmet kitchen, air conditioning, a balcony overlooking an apple orchard, and fast WiFi, with nearby access to hiking trails, swimming holes, skiing at Sugarbush and Middlebury Snow Bowl, and water activities on Lake Champlain and Lake Dunmore.

Best pet friendly Middlebury, VT holiday rentals

Among the 31 accommodations in Middlebury, VT, here are the 3 best pet friendly rentals

Cider Mill Rd. Farmhouse - Middlebury, VT
Middlebury, VT
25/06 – 27/06
SG$1030/nightTotal: SG$2060 (2 )

Cider Mill Rd. Farmhouse

1 2
apartment , Cornwall
This Cornwall flat is located in Cornwall, Vermont, 3.2 kilometres from Middlebury College and the town centre.
This dog-friendly apartment accommodates up to 8 guests and features a kitchen with a freezer, microwave, and dishwasher, plus air conditioning, a garden, and two bathrooms, offering scenic Green Mountain views.
Private Cozy Apartment • Near Middlebury - Middlebury, VT
9.9 90 reviews
Middlebury, VT
01/08 – 30/09
SG$180/nightTotal: SG$10800 (60 )

Private Cozy Apartment • Near Middlebury

1 2
apartment , Middlebury
This charming apartment is situated just a short walk from the centre of Middlebury, offering easy access to shops, restaurants, and local attractions. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment is a comfortable and stylish one-bedroom flat, ideal for solo travellers or couples, with a maximum capacity of three guests. It features modern amenities such as fast Wi-Fi, two smart TVs, a well-equipped kitchen, and air conditioning, ensuring a pleasant stay.
Tasteful Two Bedroom Just Minutes To Middlebury! - Middlebury, VT
10 108 reviews
Middlebury, VT
18/07 – 01/08
SG$372/nightTotal: SG$5208 (14 )

Tasteful Two Bedroom Just Minutes To Middlebury!

2 1
apartment , New Haven
This Vermont apartment, situated on a 25-acre estate 6.4km north of Middlebury and 45km south of Burlington, offers convenient access to Middlebury College (6.4km away) and Central Vermont's attractions.
The recently renovated two-bedroom flat sleeps four, boasting a gourmet kitchen, 65" smart TV, fast WiFi, a balcony overlooking a historic apple orchard, and shared access to laundry facilities, a fire pit, grill, and picnic area.
©2026 cozycozy.com