Bed and Breakfast in Bennington, VT

16 available b&b offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Bennington, VT bed and breakfast
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

16 Bed and Breakfasts in Bennington, VT

Best Bennington, VT bed and breakfasts with breakfast included

Knotty Pine Motel - King Suite W/kitchenette - Bennington, VT
No reviews

Knotty Pine Motel - King Suite W/kitchenette

B&B, Bennington
This guest house in Bennington offers a peaceful retreat, located just 800 meters from the town centre, providing convenient access to local amenities and historical sites.
The property features one bedroom and one bathroom, accommodating up to two guests, with amenities including air conditioning, Wi-Fi, a kitchen, and a swimming pool, ideal for a comfortable stay.

Best Bennington, VT bed and breakfasts with a pool

Among the 16 accommodations in Bennington, VT, here are the 2 best B&B with a pool

E And Es B And B Queen Bed Rm+ Pool & Hot Tub - Bennington, VT
10 140 reviews

E And Es B And B Queen Bed Rm+ Pool & Hot Tub

B&B, Bennington
This charming bed and breakfast is situated on East Street in Bennington, Vermont, just a few minutes from Route 7 and Route 9 and within a 48km drive of Mass MoCA, Williams College, and the Observatory. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property features a kitchen, a lounge, and a seasonal patio deck, providing multiple dining options for guests. The bed and breakfast can accommodate up to two guests and offers a range of amenities, including a swimming pool, a hot tub, a garden, and modern conveniences like air conditioning, internet access, and USB phone plug-ins.
Knotty Pine Motel - King Suite W/kitchenette - Bennington, VT
No reviews

Knotty Pine Motel - King Suite W/kitchenette

B&B, Bennington
This guest house in Bennington offers a peaceful retreat, located just 800 meters from the town centre, providing convenient access to local amenities and historical sites.
The property features one bedroom and one bathroom, accommodating up to two guests, with amenities including air conditioning, Wi-Fi, a kitchen, and a swimming pool, ideal for a comfortable stay.

Frequently asked questions about bed and breakfast in Bennington, VT

  • Are there any famous festivals in Bennington, Vermont?

    Bennington's calendar features several events. The Bennington Battle Day Parade, commemorating the Battle of Bennington, is a significant annual event. There's also the Bennington Free Concert Series, offering various musical performances throughout the summer. Specific dates vary yearly, so checking local event listings closer to your travel dates is recommended.
  • What are the best bed and breakfasts in Bennington, VT?

    Among the B&Bs in Bennington, VT, Leslie’s Bright & Cozy: Queen Room, South Shire and The Farm Cottage are the most popular ones.

  • Are there unique cultural experiences or workshops available in Bennington, Vermont?

    The Bennington Museum offers insightful exhibitions on regional history and art, providing a unique cultural experience. The Oldcastle Theatre Company provides regular theatre productions. For workshops, checking local community centres and the college's event listings might reveal pottery, art, or other craft workshops.
  • What are the best bed and breakfasts with a pool in Bennington, VT?

  • Which local specialties should not be missed in Bennington, Vermont?

    You should definitely try the maple products; Bennington is in prime maple syrup territory. Many local restaurants and shops offer maple-flavoured treats, from candy to ice cream. Also, look for local cheeses from Vermont farms; they're often available at farmers' markets and some shops.
  • What are the best bed and breakfasts with a jacuzzi in Bennington, VT?

  • What kinds of terrain and natural landscapes does Bennington, Vermont offer?

    Bennington sits in the foothills of the Green Mountains, offering a mix of rolling hills, forests, and mountain views. The area is known for its scenic beauty, with opportunities for hiking and exploring the natural environment. Expect varied terrain, from gentle slopes to more challenging inclines, especially as you head further into the mountains.
  • What are the best bed and breakfasts for families and kids in Bennington, VT?

    The best B&Bs for families and kids in Bennington, VT are South Shire, A Real Farm Vacation and Private 1800s Family Farmhouse - Lush Rolling Hills.

  • Are there any family-friendly hiking trails in Bennington, Vermont?

    Yes, there are several. The trails around Mount Anthony offer various difficulty levels, with some easier options suitable for families with younger children. Always check trail conditions and difficulty ratings before setting out. Specific trail names and details are best found on local hiking websites or maps.
  • What are the best pet friendly bed and breakfasts in Bennington, VT?

    The best pet friendly B&Bs in Bennington, VT are South Shire, The Farm Cottage and E And E’s B And B Queen Bed Rm+ Pool & Hot Tub.

  • Are there any safety tips for women travelling solo in Bennington, Vermont?

    Bennington is generally a safe place, but standard precautions are always advisable. Stick to well-lit areas at night, let someone know your itinerary, and be aware of your surroundings. As with any travel, trust your instincts and don't hesitate to ask for help if needed.
  • What are the best bed and breakfasts with parking in Bennington, VT?

    Leslie’s Bright & Cozy: Queen Room, South Shire and The Farm Cottage are the best B&Bs with parking in Bennington, VT.

  • What is the perfect week-long itinerary for Bennington, Vermont?

    A week allows for a good exploration. Days could include: exploring the Bennington Battle Monument, visiting the Bennington Museum, hiking in the Green Mountains, attending a performance at the Oldcastle Theatre Company, exploring local shops and restaurants, and perhaps a day trip to a nearby town like Manchester. This is a suggestion and can be tailored to individual interests.
  • Are there any one-of-a-kind cultural experiences or workshops to try in Bennington, Vermont?

    The Bennington Museum's collection of Vermont art and history is unique to the region. Checking local listings for craft workshops or demonstrations at the time of your visit may reveal opportunities to learn about local crafts, such as quilting or woodworking.
  • What are some great opportunities to engage with locals and explore the culture of Bennington, Vermont?

    Visiting local farmers' markets is a great way to meet people and sample regional produce. Stopping at local cafes and restaurants allows interaction with staff and other patrons. Attending local events, such as concerts or festivals, offers further opportunities to engage with the community and experience the local culture firsthand.

Nearby regions

Best Bennington, VT bed and breakfasts with parking

South Shire - Bennington, VT
9.0 346 reviews

South Shire

B&B, Bennington
South Shire is a charming bed and breakfast in Bennington, Vermont, located just two miles from the Bennington Battle Monument. The property enjoys excellent ratings for cleanliness, location, and overall experience.
The guest house offers one bedroom and bathroom, perfect for a couple or solo traveller. Guests can enjoy a range of amenities including a spa, fitness centre, bar, and garden, as well as access to a terrace, jacuzzi, and free parking.
South Shire - Bennington, VT
No reviews

South Shire

B&B, Bennington
South Shire is conveniently located in the centre of Bennington, within walking distance of the Bennington Arts Guild Gallery, Harmon Hill, and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display. The bed and breakfast offers a charming and comfortable stay in the heart of this historic town.
The guest house has a single bathroom and provides a restaurant on-site, free Wi-Fi, parking, air conditioning, and concierge services. Guests can enjoy a pet-friendly atmosphere, press services, and the option to arrange transfers through the hotel staff.
Welcome To Woodford Rest Suite 5! - Bennington, VT
10 5 reviews

Welcome To Woodford Rest Suite 5!

B&B, Woodford
Woodford Rest is a private suite located in Woodford, 1.6 kilometres from Prospect Mountain Ski Area and 3.2 kilometres from the Appalachian Trail and Long Trail, with direct access to snowmobile routes within the national forest.
This accommodation for up to five guests offers air conditioning, internet access, a kitchen, and one bathroom, with additional space for toy haulers and opportunities for outdoor fires.
E And Es B And B Queen Bed Rm+ Pool & Hot Tub - Bennington, VT
10 140 reviews

E And Es B And B Queen Bed Rm+ Pool & Hot Tub

B&B, Bennington
This charming bed and breakfast is situated on East Street in Bennington, Vermont, just a few minutes from Route 7 and Route 9 and within a 48km drive of Mass MoCA, Williams College, and the Observatory. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property features a kitchen, a lounge, and a seasonal patio deck, providing multiple dining options for guests. The bed and breakfast can accommodate up to two guests and offers a range of amenities, including a swimming pool, a hot tub, a garden, and modern conveniences like air conditioning, internet access, and USB phone plug-ins.

Best Bennington, VT bed and breakfasts with a garden

E And Es B And B Queen Bed Rm+ Pool & Hot Tub - Bennington, VT
10 140 reviews

E And Es B And B Queen Bed Rm+ Pool & Hot Tub

B&B, Bennington
This charming bed and breakfast is situated on East Street in Bennington, Vermont, just a few minutes from Route 7 and Route 9 and within a 48km drive of Mass MoCA, Williams College, and the Observatory. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property features a kitchen, a lounge, and a seasonal patio deck, providing multiple dining options for guests. The bed and breakfast can accommodate up to two guests and offers a range of amenities, including a swimming pool, a hot tub, a garden, and modern conveniences like air conditioning, internet access, and USB phone plug-ins.
South Shire - Bennington, VT
9.0 346 reviews

South Shire

B&B, Bennington
South Shire is a charming bed and breakfast in Bennington, Vermont, located just two miles from the Bennington Battle Monument. The property enjoys excellent ratings for cleanliness, location, and overall experience.
The guest house offers one bedroom and bathroom, perfect for a couple or solo traveller. Guests can enjoy a range of amenities including a spa, fitness centre, bar, and garden, as well as access to a terrace, jacuzzi, and free parking.
©2026 cozycozy.com