Vacation rentals in Bennington, VT

48 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 48 accommodations in Bennington, VT, here are the 4 best family friendly rentals

Enjoy Summer & Private, Peace And  Relaxation - Bennington, VT
9.8 42 reviews

Enjoy Summer & Private, Peace And Relaxation

apartment, Hoosick Falls
This secluded vacation rental is located on a private 5-acre lot on the border of New York and Vermont, within a 30-60 minute drive of several ski areas, offering a peaceful escape from the city. This charming home features two bathrooms and can accommodate up to five guests.
The property offers a variety of amenities, including a fully equipped kitchen, air conditioning, free parking, and high-speed internet. Enjoy the expansive deck, relax in the oversized soaking tub, or gather around the fire pit for a memorable evening.
"The Chambers" - Bennington, VT
9.8 112 reviews

"The Chambers"

apartment, Pownal
This apartment is located in Pownal, Vermont, just a short drive from attractions like Williams College, the Williamstown Theatre Festival, and the Clark Art Museum. The apartment enjoys excellent user, location, and cleanliness ratings.
The apartment is housed in a historic inn with original features and a private entrance. Guests can enjoy amenities like Wi-Fi, satellite TV, a laundry room, outdoor seating, a fire pit, and a BBQ.
Sold. Not Taking Any Stays - Bennington, VT
9.3 21 reviews

Sold. Not Taking Any Stays

apartment, Bennington
This 5-bedroom home is located in a friendly Bennington neighborhood, just a short drive from the Bennington Battle Monument and the Bennington Museum. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The home is spacious and comfortably accommodates up to 7 guests. Enjoy the amenities including a fully equipped kitchen, a wood-burning stove, a large deck with a grill, and a shared yard.
The Little Hoosic House - Bennington, VT
9.6 96 reviews

The Little Hoosic House

house, Hoosick Falls
This Hoosick Falls house rental boasts a secluded 3-acre setting along the Little Hoosic River, offering mountain views and proximity to Grafton Lakes State Park, Jiminy Peak, and the Grafton Peace Pagoda.
The one-bedroom, one-bathroom cottage comfortably sleeps two guests and features a fully equipped kitchen with a refrigerator, freezer, and microwave, air conditioning, and internet access, plus a garden.

Best pet friendly Bennington, VT vacation rentals

Among the 48 accommodations in Bennington, VT, here are the 2 best pet friendly rentals

Green Acres Glamping Tent - Bennington, VT
9.9 145 reviews

Green Acres Glamping Tent

glamping, Hoosick Falls
This Hoosick Falls, New York house rental is a one-bedroom, one-bathroom cottage ideal for couples seeking a peaceful retreat near the village center, with potential access to nearby hiking trails and historical sites like the Bennington Battle Monument in Vermont (exact distances require further clarification).
The property offers a tranquil setting, accommodating up to two guests and including amenities such as a fully equipped kitchen and garden (additional details on specific amenities and square footage are needed).
Arnies Adorable Tiny Cabin @ Green Acres - Bennington, VT
9.8 131 reviews

Arnies Adorable Tiny Cabin @ Green Acres

house, Hoosick Falls
This tiny cabin is located in Hoosick Falls, just a short drive from the historic downtown area and a scenic walk to the Hoosic River. The cabin has received excellent ratings for cleanliness, location, and overall user experience.
The cozy cabin features a unique open-concept layout and can accommodate up to three guests. It includes a small fridge, Keurig coffee maker, gas grill, and basic kitchenware, as well as an outdoor shower and fire pit for enjoying the surrounding nature.

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 48 accommodations in Bennington, VT, here are the 1 best rentals with a pool

24 Acre Southern Vermont Luxury Hilltop Retreat - Private Pool & Panoramic Views - Bennington, VT
9.6 5 reviews

24 Acre Southern Vermont Luxury Hilltop Retreat - Private Pool & Panoramic Views

apartment, Stamford
This secluded hillside residence in Stamford, Vermont, sits on 24 private acres with Green Mountain views, located 7 minutes from Mass MoCA and 20 minutes from The Clark Art Institute.
This 4500 sq ft home accommodates up to 8 guests with 4 bedrooms, 3 bathrooms, a bonus sleeping room, a stone fireplace, a bar area, and a private in-ground swimming pool, with nearby access to hiking, skiing at Mount Snow (22 miles) and Stratton Mountain (38 miles), and golf.

Best Bennington, VT vacation rentals with parking

The Cozy Cottage @ Woodford Lake - Bennington, VT
9.3 16 reviews

The Cozy Cottage @ Woodford Lake

apartment, Woodford
This lakefront cabin is located on Woodford Lake, also known as Big Pond, and is just a short drive from the charming town center of Woodford. The cabin has received excellent ratings for its location, cleanliness, and overall experience.
The cabin has three bedrooms and can comfortably accommodate up to five guests. Guests can enjoy a fully equipped kitchen, a cozy gas fireplace, and stunning lake views from the bedrooms and living room, along with direct access to the lake for swimming, fishing, or simply relaxing by the water.
Cozy Loft Steps From Vt Downtown - Bennington, VT
9.8 7 reviews

Cozy Loft Steps From Vt Downtown

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.
Charming Vermont House. Mountain Views And Sauna - Bennington, VT
9.7 21 reviews

Charming Vermont House. Mountain Views And Sauna

apartment, Stamford
This Vermont house rental in Stamford boasts three bedrooms and two bathrooms, sleeping up to seven guests, and offers stunning mountain views from its hilltop location.
The property includes a modern interior, a fully equipped kitchen with a fridge and freezer, plus parking and internet access; specific distances to local attractions are not provided.
Charming 3-bedroom Vermont House With Outdoor Sauna And Mountain Views - Bennington, VT
9.8 7 reviews

Charming 3-bedroom Vermont House With Outdoor Sauna And Mountain Views

apartment, Stamford
This renovated house in Stamford is located 30 miles from ski slopes and near the North Adams Public Library, East Hoosac Quaker Meetinghouse, Hopkins Observatory, and the 62 Center for Theater and Dance.
This 3-bedroom, 2-bathroom house accommodates up to 7 guests with amenities including a private sauna, WiFi, and parking, offering convenient access to North Adams Center and North Adams Gateway Center for shopping.
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