Compare Vacation Rentals & Airbnb in Middlebury, VT

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Middlebury, VT vacation rentals
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31 Rentals and Airbnb in Middlebury, VT

Best family friendly Middlebury, VT vacation rentals

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

Close To College-cheerful, Quiet, 2 Bedroom Home - Middlebury, VT
10 122 reviews
Middlebury, VT
25/06 – 27/06
$419/nighttotal: $838 (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
$871/nighttotal: $12194 (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.
Green Mountain Village Getaway In Picturesque Bristol, Vermont. - Middlebury, VT
10 7 reviews
Middlebury, VT
18/07 – 01/08
$564/nighttotal: $7896 (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.

Best Middlebury, VT vacation rentals with parking

Middlebury In-town Oasis - Middlebury, VT
9.3 28 reviews
Middlebury, VT
25/06 – 27/06
$514/nighttotal: $1028 (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.
Tasteful Two Bedroom Just Minutes To Middlebury! - Middlebury, VT
Middlebury, VT
18/07 – 01/08
$440/nighttotal: $6160 (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.
Vermont Modern Farmhouse + 46 Acres + Spectacular - Middlebury, VT
10 4 reviews
Middlebury, VT
18/07 – 01/08
$659/nighttotal: $9226 (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.
Middlebury Bungalow - Middlebury, VT
10 8 reviews
Middlebury, VT
25/06 – 27/06
$447/nighttotal: $894 (2 )

Middlebury Bungalow

1 2
apartment , Middlebury
This two-bedroom flat in Middlebury is centrally located in a quiet neighbourhood near the woods, offering convenient access to downtown dining and activities, and is within walking distance of local shops.
This accommodation for up to four guests includes a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, parking, a dedicated office space, and keypad entry, making it an ideal base for skiing, running, and biking the Trail Around Middlebury.

Frequently Asked Questions about vacation rentals in Middlebury, VT

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

    Middlebury is a charming town with plenty to see. You can visit the beautiful Middlebury College campus, explore the Sheldon Museum, or take a stroll through the historic downtown area. For a scenic drive, head to the nearby Bread Loaf Mountain for stunning views of the Green Mountains.
  • 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.

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

    The scenic Otter Creek Trail is a popular choice for both walking and cycling, offering a flat and easy route along the river. For a more challenging ride, try the Middlebury Bike Path, which climbs up to the top of Chipman Hill for panoramic views of the town.
  • 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 great place for outdoor enthusiasts. You can go hiking in the Green Mountains, kayaking on Lake Champlain, or skiing at Snow Bowl, a local ski resort with great views of the Champlain Valley. There are also golf courses and tennis courts available.
  • 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 conveniently located close to other Vermont towns and cities. You can easily drive to Burlington, the largest city in Vermont, which is about a 45-minute drive away. Rutland, another charming town with a vibrant arts scene, is about a 30-minute drive from Middlebury.
  • What amenities are commonly available in vacation rentals in Middlebury, VT?

    Most vacation rentals in Middlebury will offer basic amenities like WiFi, kitchen facilities, and laundry machines. Many also include fireplaces, hot tubs, and private decks or patios. You can often find rentals with mountain or lake views, depending on your preference.
  • What time of year is best to rent a vacation rental Middlebury, VT?

    The best time to visit Middlebury depends on what you're looking for. Spring and autumn are lovely for hiking and enjoying the changing colours of the leaves. Summer is great for swimming in Lake Champlain and enjoying outdoor activities. Winter is perfect for skiing and snowshoeing. Middlebury is a beautiful place to visit year-round.
  • 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. You can try maple-glazed chicken, maple-pecan pancakes, or maple-glazed doughnuts. You should also try Vermont cheddar cheese, which is used in many local dishes, like cheese fondue and mac and cheese.

Destinations nearby

Best Middlebury, VT vacation rentals with a balcony

Tasteful Two Bedroom Just Minutes To Middlebury! - Middlebury, VT
Middlebury, VT
18/07 – 01/08
$440/nighttotal: $6160 (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 vacation rentals

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

Charming One Bedroom Just Minutes To Middlebury! - Middlebury, VT
10 183 reviews
Middlebury, VT
25/06 – 27/06
$314/nighttotal: $628 (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.
Forest Getaway - Middlebury, VT
Middlebury, VT
01/08 – 30/09
$587/nighttotal: $35220 (60 )

Forest Getaway

1 2
apartment , New Haven
This private woodland dwelling is situated 8 kilometres from Middlebury and Bristol, offering proximity to Lake Champlain and numerous state parks.
This apartment accommodates up to 8 guests and features 3 bathrooms, a kitchen, air conditioning, and internet, ideal for exploring Vermont's outdoor activities.
Middlebury Carriage House - Middlebury, VT
10 9 reviews
Middlebury, VT
25/06 – 27/06
$451/nighttotal: $902 (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
$1120/nighttotal: $2240 (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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