Best Holiday rentals and Airbnb offers in Middlebury, VT
Middlebury, VT
01/08 – 30/09
SG$335/nightTotal: SG$20100 (60 )
Modern Woodland Escape W Wshr Dryer And Large Yard
1 2
apartment , Ripton
This secluded craftsman bungalow in Ripton offers privacy on a wooded lot, situated minutes from the Ripton General Store, 8 kilometres from the Breadloaf campus, a 15-minute drive to Middlebury, and 40 minutes to Sugarbush ski resort, with convenient access to Green Mountain National Forest for outdoor pursuits. This detached dwelling spans 139 square metres, accommodates up to four guests with one bedroom and one bathroom, and features a fully equipped kitchen, in-unit laundry, central air conditioning, parking, and a dedicated electric vehicle charger.
10 45 reviews
Middlebury, VT
25/06 – 27/06
SG$427/nightTotal: SG$854 (2 )
Renovated East Middlebury House
1 2
apartment , Middlebury
This recently renovated Middlebury house is situated in a walkable village, a short distance from the Waybury Inn pub and restaurant, and within a few kilometres of Middlebury College and the Middlebury College Snow Bowl. The two-bedroom, two-bathroom property sleeps four guests and offers a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, and access to outdoor space; winter sports enthusiasts will appreciate its proximity to the Snow Bowl.
10 7 reviews
Middlebury, VT
25/06 – 27/06
SG$242/nightTotal: SG$484 (2 )
Walk To Middlebury College
1 2
apartment , Middlebury
This Middlebury studio apartment is conveniently located within walking distance of Middlebury College and the town centre, offering easy access to shops, restaurants, and cultural attractions. The self-contained unit, sleeping up to two guests, features a kitchen, air conditioning, and private entrance, and benefits from parking nearby (confirmation required).
10 20 reviews
Middlebury, VT
25/06 – 27/06
SG$1247/nightTotal: SG$2494 (2 )
In Town, Sparrow’s Nest Lovely 2/1 Apt
1 2
apartment , Middlebury
This two-bedroom flat is situated in Middlebury, just a short walk from the college campus, athletic fields, and the town centre, and is a five-minute drive from Porter Hospital. It has received excellent ratings for location, cleanliness, and user experience. The self-catering property sleeps four guests and is equipped with a modern kitchen, a comfortable living area with a smart TV, and a private gym with a Peloton, rowing machine, and free weights. Guests can also enjoy the shared backyard with a fire pit and benefit from the convenience of a washer and dryer.
Middlebury, VT
01/08 – 30/09
SG$260/nightTotal: SG$15600 (60 )
Easy Access To Middlebury
1 2
apartment , Middlebury
This two-bedroom flat in Middlebury is centrally located, offering easy access to the town centre and Middlebury College, which is within a 5-minute drive or a walkable distance via the Trail Around Middlebury (TAM). This pet-friendly apartment accommodates up to four guests and includes internet, air conditioning, and a kitchen, with the added benefit of a fitness centre and proximity to outdoor pursuits on the TAM.
9.9 95 reviews
Middlebury, VT
01/08 – 30/09
SG$124/nightTotal: SG$7440 (60 )
Miss Dee's Retreat
1 2
house , Salisbury
This detached garage apartment is situated in a wooded area just outside Salisbury, offering a tranquil setting with proximity to woodland sounds and wildlife. This family-friendly accommodation for three guests includes a fully equipped kitchen, a queen-sized bed, a fold-out sleeper chair, a patio with a charcoal grill and fire pit, and access to light exercise equipment, all complemented by complimentary fresh eggs from on-site hens and reliable WiFi.
10 12 reviews
Middlebury, VT
01/08 – 30/09
SG$672/nightTotal: SG$40320 (60 )
Cape Style Vermont Farm House
1 2
apartment , Cornwall
This Cornwall farmhouse, a ten-minute drive from Middlebury, Vermont (note: the original listing incorrectly states Cornwall as the destination), offers stunning Green Mountain views and proximity to Lake Champlain. Sleeping eight guests across three bedrooms and two bathrooms, this self-catering property boasts a fitness centre, air conditioning, and ample parking, alongside on-site recreational opportunities including lawn games and a campfire.
10 8 reviews
Middlebury, VT
25/06 – 27/06
SG$411/nightTotal: SG$822 (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.
Middlebury, VT
01/08 – 30/09
SG$540/nightTotal: SG$32400 (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.
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.
9.9 15 reviews
Middlebury, VT
25/06 – 27/06
SG$345/nightTotal: SG$690 (2 )
Midd Manor
1 2
apartment , Middlebury
This Middlebury apartment is conveniently located within walking distance of the town centre and the TAM trails, offering easy access to restaurants such as Fire and Ice and 2 Brothers Tavern, and is approximately 72–80 km from both Killington and Sugarbush ski resorts. The self-catering flat comprises one bedroom, one bathroom, and sleeps two guests, featuring amenities including air conditioning, parking, and internet access; nearby attractions include the American Flatbread restaurant and a natural food co-op.
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.
Best family friendly Middlebury, VT holiday rentals
Among the 31 accommodations in Middlebury, VT, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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).
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.
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?
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?
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
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
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.
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.
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.