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

Dreamy & Stylish Log Cabin Near Town W/ Fast Wifi - Bennington, VT
10 82 reviews
Bennington, VT
07/01 – 07/08
$408/nighttotal: $2856 (7 )

Dreamy & Stylish Log Cabin Near Town W/ Fast Wifi

1 2
apartment , Bennington
This log cabin is located near Bennington, Vermont, just a short drive from Mount Snow, Manchester Center, and Mass MOCA, offering easy access to the area's attractions. The cabin boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The cabin offers a spacious open floor plan perfect for family gatherings or relaxing evenings with friends, accommodating up to six guests. The fully equipped kitchen, entertainment options in the basement, and a peaceful wooded setting provide everything you need for a memorable vacation.
Private Home On 37 Acres With Stunning Mountain Views - Bennington, VT
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.
Walkable Modern 2br In Downtown - Right Unit - Bennington, VT
9.7 62 reviews
Bennington, VT
10/05 – 10/07
$287/nighttotal: $574 (2 )

Walkable Modern 2br In Downtown - Right Unit

1 2
apartment , Bennington
This Bennington apartment is conveniently located in the heart of town, just a short walk from Walmart and Hannaford, with easy access to nearby ski areas, mountains, hiking trails, and lakes. The apartment has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travelers.
This comfortable rental features two bedrooms and one bathroom, comfortably accommodating up to six guests. The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, a shared garden, and parking, ensuring a pleasant and convenient stay.
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

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.
The Deer Crib - Bennington, VT
10 44 reviews
Bennington, VT
06/27 – 07/04
$137/nighttotal: $959 (7 )

The Deer Crib

1 2
cabin , Hoosick Falls
This off-grid cabin is located near Hoosick Falls, on 230 acres of meadows and woods, offering a secluded and tranquil escape. It boasts excellent user, location, and cleanliness ratings. This charming cabin is perfect for couples seeking a peaceful getaway. The cabin provides a wood-burning stove for warmth, potable water for convenience, and outdoor activities like hiking, snowshoeing, and cross-country skiing.
New Log Cabin - Privacy, Views, Trails - Bennington, VT
Bennington, VT
06/27 – 07/04
$543/nighttotal: $3801 (7 )

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.

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 Bedroom Guest House On Dead-end Rd - Bennington, VT
9.6 129 reviews
Bennington, VT
07/01 – 07/08
$154/nighttotal: $1078 (7 )

1 Bedroom Guest House On Dead-end Rd

1 2
apartment , Bennington
This Bennington apartment is conveniently located just 5 minutes from Southwestern Vermont Medical Center and a 15-minute walk from the lively Main Street, offering easy access to shops, restaurants, and local attractions. The apartment consistently receives excellent ratings for cleanliness, location, and overall user experience.
The apartment features a private patio, a full kitchen, and parking. It comfortably accommodates up to two guests and is perfect for those seeking a peaceful and private stay close to Bennington's attractions, including Mount Snow for skiing and MassMoCA, a contemporary art museum.

Best Bennington, VT vacation rentals with parking

Bennington Gem W/ Smart Tv Near Historic District! - Bennington, VT
Bennington, VT
10/05 – 10/07
$257/nighttotal: $514 (2 )

Bennington Gem W/ Smart Tv Near Historic District!

1 2
, 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.
Cozy Loft Steps From Vt Downtown - Bennington, VT
9.6 5 reviews
Bennington, VT
10/05 – 10/07
$238/nighttotal: $476 (2 )

Cozy Loft Steps From Vt Downtown

1 2
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.
< 1 Mi To Historic District! Retreat In Bennington - Bennington, VT
10 1 review
Bennington, VT
07/01 – 07/08
$212/nighttotal: $1484 (7 )

< 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.
Charming 2-bedroom Apartment In Superb Bennington With Wifi - Bennington, VT
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.
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