Vacation rentals in Bennington, VT

37 available vacation rental offers

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Bennington, VT vacation rentals
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Best Vacation rentals and Airbnb offers in Bennington, VT

Best family friendly Bennington, VT vacation rentals

Among the 37 accommodations in Bennington, VT, here are the 4 best family friendly rentals

White Rock Farm - Bennington, VT
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.
Charming Restored Log Cabin In Hoosick Falls Ny On The Vermont Border - Bennington, VT
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.
Vermont Downtown Oasis - Two Bedroom In Picturesque Downtown - Bennington, VT
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.
Quiet Apartment Getaway - Bennington, VT
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

Modern, Stylish Apartment On Stunning Horse Farm In Shaftsbury Vermont. - Bennington, VT
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.
Walkable Modern 2br In Downtown - Left Unit - Bennington, VT
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.
1920's Bennington Vermont Guest Barn - Bennington, VT
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.
Vermont🍁🌲 - Bennington, VT
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?

    Cozy Modern Sugar House With Spectacular Views, Victorian Home In Bennington - Vermont and Scenic Vermont Studio are the most popular Airbnb and vacation rentals in Bennington, VT among travelers.

  • 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?

    Among the Airbnbs in Bennington, VT, Cozy Modern Sugar House With Spectacular Views, Scenic Vermont Studio and Cooper's Place are the most popular ones.

  • 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?

    The best vacation rental with a pool in Bennington, VT is Historic Home In Old Bennington - Vermont.

  • 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?

    The best rentals for families and kids in Bennington, VT are Suite Sunset 311 Rice Lane Bennington Vt, Two Brooks Lodge and Awesome 3 Bedroom Apartment Close To It All.

  • 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?

    Two Brooks Lodge and Historic Inn Wbar Room - Hot Tub - 6 Bedrooms are the best vacation rentals or Airbnb 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

< 1 Mi To Historic District! Retreat In Bennington - Bennington, VT
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

Awesome 3 Bedroom Apartment Close To It All - Bennington, VT
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.
Cozy Loft Steps From Vt Downtown - Bennington, VT
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.
Green Mountain Getaway - Bennington, VT
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.
The Old Pine House - Bennington, VT
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.
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