Holiday Rentals in Middlebury, VT

31 available vacation rental offers

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Middlebury, VT holiday rentals
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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 2 best family friendly rentals

Updated Farmhouse Minutes From Middlebury - Middlebury, VT
10 35 reviews
Middlebury, VT
25/06 – 27/06
SG$538/nighttotal: SG$1076 (2 )

Updated Farmhouse Minutes From Middlebury

1 2
apartment , Weybridge
This Weybridge farmhouse, situated on Sheep Farm Road, is just over 1.6km from Middlebury town centre and Middlebury College, offering convenient access to local amenities.
The three-bedroom property, renovated in 2022, boasts an open-plan kitchen, dining, and living area, a large garden with firepit and deck, parking for three vehicles, and sleeps up to six guests.
Tiny Sparrow House,  Luxury & Charm In Middlebury - Middlebury, VT
10 16 reviews
Middlebury, VT
25/06 – 27/06
SG$2128/nighttotal: SG$4256 (2 )

Tiny Sparrow House, Luxury & Charm In Middlebury

1 2
apartment , Middlebury
This charming house is located in the heart of Middlebury, just a short walk from both Middlebury College and the town centre, making it ideal for exploring the area's attractions and amenities. The property consistently receives excellent ratings from previous guests for its cleanliness, location and overall experience.
The house offers comfortable accommodation for up to eight guests with four bedrooms and three bathrooms. Guests can enjoy a fully equipped kitchen, a large garden with a swing, gas grill, fire pit and Adirondack chairs, as well as free parking.

Best Middlebury, VT holiday rentals with parking

Vermont Modern Farmhouse + 46 Acres + Spectacular - Middlebury, VT
10 4 reviews
Middlebury, VT
18/07 – 01/08
SG$606/nighttotal: SG$8484 (14 )

Vermont Modern Farmhouse + 46 Acres + Spectacular

3 1
apartment , New Haven
This New Haven, Vermont apartment is a lower-level, self-contained unit on a 46-acre property near Lincoln Peak Vineyard and The Golf Club, with Vergennes Falls Park and Rokeby Museum a short drive away.
The 148 square metre (approximately 1590 square feet) property offers three bedrooms sleeping five, two bathrooms, a fully equipped kitchen including dishwasher, and a Vermont granite terrace with fire pit; nearby activities include boating, fishing, horse riding and mountain climbing.
Charming One Bedroom Just Minutes To Middlebury! - Middlebury, VT
10 183 reviews
Middlebury, VT
25/06 – 27/06
SG$289/nighttotal: SG$578 (2 )

Charming One Bedroom Just Minutes To Middlebury!

1 2
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.
Modern Woodland Escape W Wshr Dryer And Large Yard - Middlebury, VT
Middlebury, VT
18/07 – 01/08
SG$300/nighttotal: SG$4200 (14 )

Modern Woodland Escape W Wshr Dryer And Large Yard

1 1
house , Ripton
This Ripton holiday home is situated 35 kilometres from Mad River, 15 kilometres from Branbury State Park, and 16 kilometres from Texas Falls Recreation Area.
This property offers accommodation for six guests with a floor area of 139 square meters, featuring a fully equipped kitchen, air conditioning, on-site parking, and complimentary WiFi, with a large garden for outdoor activities.
Middlebury In-town Oasis - Middlebury, VT
9.3 28 reviews
Middlebury, VT
18/07 – 01/08
SG$333/nighttotal: SG$4662 (14 )

Middlebury In-town Oasis

1 1
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

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.
Middlebury Carriage House - Middlebury, VT
10 9 reviews
Middlebury, VT
25/06 – 27/06
SG$415/nighttotal: SG$830 (2 )

Middlebury Carriage House

1 2
apartment , Middlebury
This two-bedroom carriage house is situated just under 3.2 kilometres from Middlebury College, offering easy access to the campus and the Vermont countryside.
This newly renovated apartment accommodates up to four guests, featuring two bedrooms with queen beds, a well-equipped kitchen, a second-story porch with views, and a screened porch with shuffleboard, all within a 1.6-kilometre radius of the college.
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.
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