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 1 best family friendly rentals

!Charming Cabin,  Great Views - Bennington, VT
9.5 193 reviews

!Charming Cabin, Great Views

cabin, Shaftsbury
This Shaftsbury cabin is located just 20-30 minutes from both Bennington and Manchester, offering a peaceful escape in the Vermont countryside. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The 1150-square-foot cabin comfortably accommodates up to 7 guests with 2 bedrooms and 1 bathroom. Enjoy a range of amenities including a full kitchen, a fire pit, a porch swing, a hammock, and access to hiking trails, a pond, and a working farm with chickens, ducks, and goats.

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).
Stay In An Industrial, Cozy & Artsy Sleeping Loft. - Bennington, VT
9.1 54 reviews

Stay In An Industrial, Cozy & Artsy Sleeping Loft.

apartment, Hoosick Falls
This apartment is located on the second floor of a renovated 19th-century department store in the heart of Hoosick Falls, just steps away from the village's main street and within walking distance of the historic Hoosic River. The apartment has received excellent ratings for location, cleanliness, and overall experience. The apartment has a unique loft-style layout and can comfortably accommodate two guests. Amenities include a fully equipped kitchen, a cozy sleeping loft, complimentary coffee and tea, and access to a first-floor art gallery and artisanal pizza restaurant.

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

Serene Getaway In The Vermont National Forrest - Bennington, VT
9.4 10 reviews

Serene Getaway In The Vermont National Forrest

apartment, Woodford
This 4-bedroom apartment is located near the Vermont National Forest, a short distance from the Appalachian Trail, MASS MOCA, the Clark Art Museum, and the Williamstown Summer Theater. It has received excellent user and location ratings and a very good cleanliness rating.
The apartment comfortably accommodates 8 guests and boasts a fully equipped kitchen, a Jacuzzi, a garden, a sauna, and parking. Enjoy a peaceful retreat with access to nearby hiking trails, cultural attractions, and outdoor recreation opportunities.
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