Best Vacation rentals and Airbnb offers in Bennington, VT
9.7 81 reviews
Bennington, VT
07/01 – 07/08
$125/nighttotal: $875 (7 )
North Bennington, Vt Conveniently Located Unit.
1 1
apartment , Bennington
This ground-level apartment is located in North Bennington, a short distance from Bennington College and within walking distance of Park McCullough Mansion and downtown amenities. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment features a bedroom and a bathroom, comfortably accommodating up to four guests. Enjoy a peaceful environment, a fully equipped kitchen, and a spacious backyard with a patio, fire pit, and access to walking trails, a nearby lake, and a kayak for your use.
Bennington, VT
07/01 – 07/08
$209/nighttotal: $1463 (7 )
Bennington Gem W/ Smart Tv Near Historic District!
1 1
, Bennington
This Bennington cottage offers contactless check-in/out and is within walking distance of downtown Bennington, near Hemmings Motor News, Harmon Hill, and the Bennington Arts Guild Gallery. The 2-guest cottage features a kitchen with a fridge, microwave, and dishwasher, one bathroom, free on-site parking, and Wi-Fi.
9.9 95 reviews
Bennington, VT
07/01 – 07/08
$134/nighttotal: $938 (7 )
Cozy Loft Steps From Vt Downtown
1 1
apartment , Bennington
This one-bedroom loft apartment is situated in the heart of Old Bennington, within walking distance of the Bennington Monument and the downtown area. The apartment boasts a spacious bay window sitting area, a private balcony with views of Mount Anthony, and modern furnishings, making it perfect for a couple's getaway.
Bennington, VT
06/27 – 06/29
$728/nighttotal: $1456 (2 )
New Log Cabin - Privacy, Views, Trails
1 2
cabin , Searsburg
This lodge in Searsburg offers a 5-minute walk to Green Mountain National Forest and is a short drive to Woodford State Park and Mount Snow. This cabin accommodates 16 guests with 2 bathrooms and provides convenient access to cultural attractions like the Jim McGrath Gallery and Studio.
9.8 7 reviews
Bennington, VT
10/05 – 10/07
$165/nighttotal: $330 (2 )
Charming 2-bedroom Apartment In Superb Bennington With Wifi
2 2
apartment , Bennington
This Bennington apartment rental is conveniently located near Bennington Potters Yard and Fiddlehead at Four Corners, providing easy access to Green Mountain National Forest and Lake Shaftsbury State Park. This 1000-square-foot unit sleeps up to four guests comfortably in two bedrooms and one bathroom, offering amenities such as WiFi, a full kitchen (including a fridge, microwave, and dishwasher), a washer, and on-site parking, plus a spa.
9.3 32 reviews
Bennington, VT
06/27 – 06/29
$1823/nighttotal: $3646 (2 )
Private Home On 37 Acres With Stunning Mountain Views
5 2
apartment , Shaftsbury
This Shaftsbury home is located 11 miles from the Bennington Battle Monument and 42 miles from Albany International Airport, offering a peaceful retreat in the Vermont countryside. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This 5-bedroom house can accommodate up to 12 guests, providing ample space for families or groups of friends. Amenities include a fully equipped kitchen, a Jacuzzi, a terrace, a garden, a spa, a tennis court, and free parking, making it ideal for relaxation and outdoor activities.
10 90 reviews
Bennington, VT
10/05 – 10/07
$212/nighttotal: $424 (2 )
Guest Cottage - Mountain Views, History & Hiking
1 2
house , Bennington
This historic cottage is located in the heart of Old Bennington. It's surrounded by renowned attractions like the Bennington Monument and just minutes from downtown amenities. It has excellent user, location, and cleanliness ratings. With one bathroom and sleeping two people, this cottage is a great choice for couples. The cottage offers amenities like air conditioning, a fitness center, parking, and a garden. Guests also have access to a kitchen and a balcony with views of the mountains.
10 6 reviews
Bennington, VT
10/05 – 10/07
$126/nighttotal: $252 (2 )
A Cozy Taste Of Vermont
1 2
apartment , Bennington
This one-bedroom, one-bathroom apartment in Bennington provides easy access to downtown attractions and local amenities. This rental offers a Vermont-themed decor, an in-unit gaming system, and accommodations designed for mid-size individuals, including considerations for doorway heights and commode accessibility, with parking and air conditioning included for up to two guests.
9.7 27 reviews
Bennington, VT
10/05 – 10/07
$326/nighttotal: $652 (2 )
Green Mountain Getaway
3 2
apartment , Bennington
This Bennington apartment rental is located within one mile of Green Mountain National Forest, Bennington Potters Yard, and Fiddlehead at Four Corners, offering easy access to outdoor recreation and local arts and crafts. This 1450-square-foot, three-bedroom, one-bathroom unit sleeps six and includes a fully equipped kitchen, in-unit laundry, free parking, and complimentary Wi-Fi.
8.5 27 reviews
Bennington, VT
07/01 – 07/08
$149/nighttotal: $1043 (7 )
Historic Downtown Apartment Near Skatepark
1 1
apartment , Bennington
This upstairs apartment is located in downtown Bennington, just off the New Walking Trail, which leads to North Bennington and is within walking distance of Main Street and its local restaurants. The apartment is situated in an older historic building, adding a unique character to the experience. The apartment features a living room, three bedrooms, a kitchen, a bathroom, and a laundry/breezeway area, providing ample space for up to six guests. The apartment offers amenities such as a fridge, microwave, internet, air conditioning, parking, and laundry facilities, making it a convenient and comfortable stay for travelers.
10 96 reviews
Bennington, VT
07/01 – 07/08
$154/nighttotal: $1078 (7 )
Modern Rustic Hideaway In Town
1 1
apartment , Bennington
This charming Bennington apartment is located just a 5-minute walk from the town center, making it easy to explore shops, restaurants, and attractions. Guests consistently rate the apartment excellent for location, cleanliness, and overall experience. The apartment features one bedroom and one bathroom, comfortably accommodating up to two guests. Amenities include a fully equipped kitchen, a fitness center, parking, and laundry facilities, ensuring a convenient and enjoyable stay.
9.7 6 reviews
Bennington, VT
07/01 – 07/08
$216/nighttotal: $1512 (7 )
Large Country Ranch On 2 Acres
4 1
apartment , Bennington
This Bennington, Vermont house is located within an hour's drive of Saratoga Springs, New York, and offers easy access to horse racing and skiing. It has excellent user, location, and cleanliness ratings. The house has four bedrooms and two bathrooms and can accommodate up to eight guests. It features a large living room with a fireplace and wraparound leather couch, an eat-in kitchen, and a wrap-around deck with mountain views. The kitchen is equipped with a bay window offering a beautiful view, and there is a full bath and laundry room off the kitchen. The house has a large bird feeder where guests can observe birds up close.
Best family friendly Bennington, VT vacation rentals
Among the 37 accommodations in Bennington, VT, here are the 4 best family friendly rentals
10 131 reviews
Bennington, VT
07/01 – 07/08
$396/nighttotal: $2772 (7 )
White Rock Farm
1 1
gîte , Bennington
This family-friendly farmhouse is located just a short drive from Bennington, Vermont, offering easy access to attractions like Bennington Potters Yard, Fiddlehead at Four Corners, and Howard Park. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The 2400 square foot farmhouse has five bedrooms, three bathrooms, and can accommodate up to 12 guests. Enjoy the riverfront location, outdoor amenities like the garden and barbecue grills, and the peacefulness of a quiet rural setting.
9.0 2 reviews
Bennington, VT
06/27 – 06/29
$1112/nighttotal: $2224 (2 )
Charming Restored Log Cabin In Hoosick Falls Ny On The Vermont Border
4 2
farm , Hoosick Falls
This four-bedroom Vermont mountain house rental near Bennington, three miles from the Green Mountain National Forest and six miles from Bennington Battlefield Park, offers a tranquil farm stay experience. Sleeping ten guests, this Hoosick Falls vacation home boasts a fully equipped kitchen with a microwave and dishwasher, air conditioning, a terrace, a garden, parking, and high-speed internet; barbecue grills are available for outdoor cooking.
10 9 reviews
Bennington, VT
10/05 – 10/07
$361/nighttotal: $722 (2 )
Vermont Downtown Oasis - Two Bedroom In Picturesque Downtown
2 2
apartment , Bennington
This downtown Bennington apartment, located in a historic building on the state register, is steps from restaurants, shops, and breweries, and a short drive from Mt. Snow, Bromley, Stratton, and Prospect Mountain ski resorts. The two-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, plus air conditioning, parking, and internet access; it offers complete privacy on the second floor above Haberdasher Wine and Provisions.
9.7 55 reviews
Bennington, VT
10/05 – 10/07
$166/nighttotal: $332 (2 )
Quiet Apartment Getaway
1 2
apartment , Bennington
This Bennington apartment rental offers a convenient Southern Vermont base for exploring nearby New York and Massachusetts, with easy access to Bennington's town center—though precise distances to specific landmarks require further inquiry. The two-bedroom, one-bathroom unit sleeps five, features a full kitchen with fridge, freezer, microwave, and dishwasher, includes parking, internet access, and boasts a unique birch forest wall for guests to personalize.
Best pet friendly Bennington, VT vacation rentals
Among the 37 accommodations in Bennington, VT, here are the 4 best pet friendly rentals
10 3 reviews
Bennington, VT
06/27 – 06/29
$351/nighttotal: $702 (2 )
Modern, Stylish Apartment On Stunning Horse Farm In Shaftsbury Vermont.
1 2
apartment , Shaftsbury
This Shaftsbury apartment rental is conveniently located near Harmon Hill and Prospect Mountain Cross-Country Ski Center, offering easy access to outdoor recreation and the Bennington Potters Yard and Fiddlehead at Four Corners. The one-bedroom unit features a queen bed, luxurious shower, cozy living room with futon, private outdoor sitting space, and access to shared gazebos, gardens, and a pond; it comfortably sleeps four guests.
9.7 49 reviews
Bennington, VT
10/05 – 10/07
$287/nighttotal: $574 (2 )
Walkable Modern 2br In Downtown - Left Unit
2 2
apartment , Bennington
This modern apartment is located in central Bennington, within walking distance of Walmart, Hannaford, and various retail stores, making it a convenient base for exploring the town. The apartment is part of a two-family home, offering a sense of privacy while still being close to other guests, with a capacity of 6 people. The apartment features a fully equipped kitchen, air conditioning, and free parking, and is pet-friendly, making it a comfortable and convenient option for families and groups.
9.6 201 reviews
Bennington, VT
07/01 – 07/08
$196/nighttotal: $1372 (7 )
1920's Bennington Vermont Guest Barn
1 1
apartment , Bennington
This charming vacation home is located in a rural setting just a mile from the Robert Frost Museum and a short drive from Bennington's downtown attractions. The property enjoys excellent user, location, and cleanliness ratings, making it a popular choice for travelers seeking a comfortable and convenient stay. The 3-bedroom, 1-bathroom apartment spans 970 square feet and comfortably accommodates up to 7 guests. The apartment offers a fully equipped kitchen, a spacious living area with cable TV, a private patio with a barbecue grill, and access to a shared garden, spa, and fire pit.
9.9 35 reviews
Bennington, VT
07/01 – 07/08
$310/nighttotal: $2170 (7 )
Vermont🍁🌲
1 1
apartment , Bennington
This apartment is located just outside of Bennington, close to shops and restaurants, offering a peaceful retreat from the town's bustle. It has received excellent ratings for location, cleanliness, and overall experience. The apartment has three bedrooms and two bathrooms, accommodating up to four guests. Amenities include a fully equipped kitchen, internet access, a garden, and parking, making it a comfortable and convenient choice for your stay.
Frequently Asked Questions about vacation rentals in Bennington, VT
What essentials should you bring along for a trip to Bennington, Vermont?
Pack for all types of weather, as Vermont's climate can be unpredictable. Comfortable walking shoes are a must for exploring the town and hiking trails. Layers are key, as temperatures can fluctuate. Don't forget insect repellent, especially during warmer months.
What are the best Airbnb and vacation rentals in Bennington, VT?
What famous events or festivals are happening in Bennington, Vermont?
Bennington hosts the Bennington Battle Day Parade each August, commemorating a significant Revolutionary War battle. Check local listings for smaller, community events throughout the year. The town also participates in the broader Vermont fall foliage celebrations.
What are the most popular Airbnbs in Bennington, VT?
What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Bennington, Vermont?
A daily budget of $150-$300 per person is a reasonable estimate, depending on your lodging choices and dining preferences. This includes accommodation, meals, local transportation (car rental recommended for exploring the surrounding area), and entry fees for attractions. Budget-conscious travelers can certainly spend less.
What are the best vacation rentals with a pool in Bennington, VT?
Where can you find the best restaurants serving local dishes in Bennington, Vermont, and what are the must-try specialties?
The Walloomsac Inn is a popular choice for upscale dining, while the Four Chimneys Inn offers a more casual atmosphere. Many local restaurants feature Vermont cheese and maple syrup in their dishes. Try the Vermont cheddar or a maple-glazed anything!
What are the best rentals for families and kids in Bennington, VT?
What are some less-famous attractions in Bennington, Vermont that are worth the visit?
The Bennington Center for the Arts offers a glimpse into the local art scene. Exploring the charming downtown area with its unique shops is also a rewarding experience. A drive along Vermont Route 9 offers scenic overlooks of the Green Mountains.
What are the best rentals or Airbnbs with a jacuzzi in Bennington, VT?
What are the best activities for engaging with locals and understanding their culture in Bennington, Vermont?
Visiting local farmers' markets allows you to interact with residents and sample local produce. Attending community events or festivals offers opportunities to connect with locals. Striking up conversations at local restaurants and shops is a great way to learn more about Bennington's culture.
What unique natural landscapes and terrain features can travelers explore in and around Bennington, Vermont?
The Green Mountains offer a variety of hiking trails, from easy walks to challenging climbs. The area is known for its forests, rolling hills, and scenic overlooks. Nearby Mount Equinox offers spectacular views from its summit.
How many days are ideal for visiting Bennington, Vermont, and what are some itinerary suggestions?
Two to three days allows for a good exploration of Bennington and its surroundings. Day one could focus on the town itself, visiting the museum and historical sites. Day two could involve hiking or exploring the Green Mountains. A third day could be dedicated to exploring nearby towns or relaxing.
Nearby regions
Best Bennington, VT vacation rentals with a pool
Among the 37 accommodations in Bennington, VT, here are the 1 best rentals with a pool
10 1 review
Bennington, VT
10/05 – 10/07
$262/nighttotal: $524 (2 )
< 1 Mi To Historic District! Retreat In Bennington
1 2
apartment , Bennington
This charming Bennington vacation rental is conveniently located within walking distance of Hemmings Motor News and a short drive from Bennington Potters Yard. The area offers a mix of historical sites, local shops, and restaurants, making it a great base for exploring Bennington. This one-bedroom apartment offers 1,000 square feet of space and can comfortably accommodate up to four guests. Amenities include a fully equipped kitchen, parking, internet access, and a washer and dryer, ensuring a comfortable and convenient stay.
Best Bennington, VT vacation rentals with parking
10 59 reviews
Bennington, VT
10/05 – 10/07
$369/nighttotal: $738 (2 )
Awesome 3 Bedroom Apartment Close To It All
1 2
apartment , Bennington
This Bennington apartment is located above a popular deli and gourmet market in the heart of downtown, putting you within walking distance of historic sights, restaurants, and a short drive to the ski mountains. The apartment has received excellent ratings for cleanliness, location, and user experience. The apartment features three bedrooms and one bathroom, comfortably accommodating up to five guests. You will enjoy a well-equipped kitchen, a three-season porch, a dedicated office/sitting room, a large living room, a washer/dryer, and a smart TV with WiFi.
9.6 5 reviews
Bennington, VT
07/01 – 07/08
$145/nighttotal: $1015 (7 )
Cozy Loft Steps From Vt Downtown
1 1
apartment , Bennington
This renovated Bennington loft apartment, located in downtown Bennington's historic district, offers easy walking access to Old Bennington's shops and restaurants, and is minutes from major highways and area ski resorts. The one-bedroom, one-bathroom unit sleeps two guests and features high vaulted ceilings, skylights, a private balcony with Mount Anthony and Bennington Monument views, fiber Wi-Fi, Chromecast with YouTube TV, and proximity to the Bennington Museum and Robert Frost Stone House Museum.
9.8 52 reviews
Bennington, VT
10/05 – 10/07
$271/nighttotal: $542 (2 )
Green Mountain Getaway
1 2
apartment , Bennington
The Green Mountain Getaway is a three-bedroom, one-bathroom house in Bennington, Vermont, offering easy access to attractions like the Bennington Battle Monument and Oldcastle Theatre Company. This Bennington vacation rental sleeps six, features a fully equipped kitchen with a fridge, microwave, and dishwasher, in-unit laundry, air conditioning, and a garden with parking; high-speed internet is also available.
10 56 reviews
Bennington, VT
10/05 – 10/07
$357/nighttotal: $714 (2 )
The Old Pine House
1 2
apartment , Bennington
This renovated 1830s home is centrally located in downtown Bennington, Vermont, within walking distance of shops, restaurants, a dispensary, and a brewery. This 2,000-square-foot house features three bedrooms, two bathrooms, and can comfortably accommodate six guests, offering a first-floor primary bedroom with an ensuite bathroom, a fully equipped kitchen, and large front and side porches.