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Bennington, VT place to stay
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80 Lodgings in Bennington, VT

Best family friendly Bennington, VT lodging

Among the 80 accommodations in Bennington, VT, here are the 4 best for families

Private 1800s Family Farmhouse, Lush Rolling Hills - Bennington, VT
9.9 59 reviews

Private 1800s Family Farmhouse, Lush Rolling Hills

gîte, Bennington
This renovated farmhouse, located just two miles from three local breweries and a 45-minute walk from Bennington College, offers a tranquil escape in a rural setting near Bennington, Vermont. With excellent user, location, and cleanliness ratings, this property provides a comfortable and enjoyable stay for visitors.
The farmhouse, suitable for up to 13 guests, features five bedrooms and three bathrooms, making it ideal for families or groups. Enjoy modern amenities such as a fully equipped kitchen, under-floor heating, high-speed Wi-Fi, and a gas fireplace, while also experiencing the charm of a historic property with stunning views of Mt. Anthony and opportunities for wildlife viewing.
Farm-to-table Eating, Good Hot Tub Soak, S'mores Around Fire Pit, Seasonal Pool! - Bennington, VT
9.4 88 reviews

Farm-to-table Eating, Good Hot Tub Soak, S'mores Around Fire Pit, Seasonal Pool!

apartment, Pownal
This apartment is situated in Pownal, Vermont, a rural mountain town just 6 miles from both Williamstown, Massachusetts and Bennington, Vermont. It has received excellent user ratings, making it a popular choice for travellers.
The apartment is a spacious one-bedroom property with a 93 square metre floor area, comfortably accommodating up to 6 guests. It offers a range of amenities, including a private courtyard, a hot tub, a seasonal pool, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.
Karin's Place: Unique And Grand Guest House W/pool - Bennington, VT
9.8 51 reviews

Karin's Place: Unique And Grand Guest House W/pool

apartment, Pownal
This charming apartment is situated in Bennington, Vermont, just 6.5 kilometres from the town of Bennington and 14.5 kilometres from Williamstown, Massachusetts, offering a peaceful retreat in the Vermont countryside. The property has received excellent ratings for its location, cleanliness, and overall guest experience.
The spacious home can comfortably accommodate up to 12 guests in its four bedrooms and two bathrooms. Enjoy a range of amenities including a private pool, hot tub, sauna, a pirate ship playground, a fireplace, and a large backyard, perfect for relaxing and entertaining.
Memes High Mountain Lake House - Bennington, VT
9.8 100 reviews

Memes High Mountain Lake House

apartment, Woodford
Meme's lake house is a mountaintop retreat in Vermont, located just 48 kilometres from Mount Snow and 24 kilometres from the town of Wilmington. The property has consistently received excellent user ratings for its location, cleanliness, and overall experience.
This spacious three-bedroom, two-bathroom holiday home can accommodate up to nine guests and spans 158 square metres. It offers a range of amenities, including a fully equipped kitchen, a terrace, a garden, and a private lakefront with a sandy beach and a screened-in gazebo.

Best Bennington, VT accommodations with a kitchen

Modern Rustic Hideaway In Town - Bennington, VT
10 97 reviews

Modern Rustic Hideaway In Town

apartment, Bennington
This one-bedroom flat is located in the centre of Bennington, just a 0.8km walk from the town's main attractions and amenities. It has received excellent ratings for its location, cleanliness and overall experience.
The flat has a modern kitchen, a comfortable living space and can accommodate up to two guests. It includes a range of amenities such as air conditioning, a fitness centre, parking, and laundry facilities.
1865 Farmhouse: Mountain, Monument & Meadow Views - Bennington, VT
9.9 25 reviews

1865 Farmhouse: Mountain, Monument & Meadow Views

apartment, Bennington
This private cottage, formerly the caretaker's residence of Colgate's Filmore Farms, offers secluded accommodation on 10 hectares of land at the base of Mount Anthony, providing direct access to hiking trails and a mere 500 metres from the Bennington Monument.
This three-bedroom, one-bathroom flat accommodates up to three guests and features a kitchen, air conditioning, parking, and internet, with expansive views of fields and mountains from its porch, ideal for those seeking winter sports or proximity to downtown Bennington's amenities.
Studio Style Vintage Garden Bungalow - Bennington, VT
9.1 147 reviews

Studio Style Vintage Garden Bungalow

studio, Shaftsbury
This Shaftsbury studio guest house, situated on a 22-acre Vermont farm near Lake Paran and Arlington Covered Bridge, offers easy access to hiking trails, including the Long Trail, and the Park McCullough House (within 1.6km).
The self-catering apartment, sleeping two guests, features a newly renovated kitchenette, a garden, parking, and on-site amenities including a gas grill, bikes (summer), farm-fresh eggs, and complimentary refreshments; a barn is available to rent for events.
Woodford Mountain - Bennington, VT
9.7 23 reviews

Woodford Mountain

apartment, Woodford
This charming Vermont house is located in Woodford, offering stunning lake views and easy access to Route 9, Mount Snow ski resort, and Bennington College. The property has consistently received excellent ratings from previous guests for its location, cleanliness, and overall experience.
The apartment has two bedrooms, two bathrooms, and a pull-out couch, comfortably accommodating up to six guests. Guests can enjoy a fully equipped kitchen, a front porch, and a new back deck, perfect for relaxing and enjoying the fresh Vermont air.

Frequently asked questions about accommodations in Bennington, VT

  • What are the must-see attractions in Bennington, Vermont?

    Bennington boasts several key attractions. The Old First Church, a historic landmark, is a must-see, as is the Bennington Battle Monument, offering panoramic views. The Robert Hull Fleming Museum at the University of Vermont houses a diverse collection, and the Bennington Museum showcases regional art and history. For a taste of local culture, exploring the downtown area with its unique shops and galleries is recommended.
  • Are there any seasonal events or cultural festivals in Bennington, Vermont?

    Bennington has a vibrant events calendar. The Bennington Battle Day Parade, held annually on 16 August, commemorates a significant historical event. The town also hosts various smaller farmers' markets and craft fairs throughout the year, often linked to seasonal harvests. Specific dates for these events vary, so checking local listings closer to your travel dates is advisable.
  • What are the most characteristic landscapes and terrains found in Bennington, Vermont?

    Bennington's landscape is characterised by rolling hills and picturesque Vermont countryside. The Green Mountains provide a stunning backdrop, with forests, meadows, and farmland dominating the scenery. The area around the Walloomsac River offers flatter terrain, contrasting with the steeper slopes found in the mountain regions. Expect a mix of rural charm and natural beauty.
  • What are the best outdoor activities in Bennington, Vermont?

    Hiking and mountain biking trails abound in the Green Mountains surrounding Bennington. The area offers opportunities for scenic drives and exploring the numerous parks and nature reserves. The Walloomsac River is suitable for leisurely walks and picnics. During winter, cross-country skiing and snowshoeing become popular activities.
  • What is the best time of year to visit Bennington, Vermont with kids?

    Summer (June-August) offers warm weather ideal for outdoor activities. Autumn (September-October) provides stunning foliage and a pleasant atmosphere for family walks and exploring the town's attractions. Spring and autumn often have fewer crowds than summer.
  • Are there any local customs to be aware of in Bennington, Vermont?

    Bennington is a friendly and welcoming town, with a strong sense of community. People generally appreciate a polite and respectful approach. There aren't any specific customs to be overly concerned about, but showing consideration for the environment and local businesses is always appreciated.
  • What are the best ways to interact with locals and learn about their culture in Bennington, Vermont?

    Striking up conversations in local shops and cafes is a great way to meet residents. Visiting the Bennington Museum offers insight into the area's history and culture. Attending local events or festivals provides opportunities to interact with the community and experience their traditions firsthand. Simply exploring the town and engaging with its unique atmosphere can offer a good feel for the local culture.
  • What are some lesser-known attractions or hidden gems in Bennington, Vermont?

    The Monument Hill and the views from the top are often overlooked. Exploring the smaller, independent shops and galleries throughout the town can reveal unique finds. Several smaller hiking trails offer stunning views without the crowds of the more popular routes. Looking beyond the main tourist attractions can lead to some pleasant surprises.
  • What are some must-try local dishes in Bennington, Vermont?

    Vermont is known for its maple products, so trying maple-flavoured treats is a must. Local cheese and craft beers are also popular choices. Many restaurants offer hearty New England-style meals, featuring locally sourced ingredients. Exploring the various restaurants and cafes in Bennington will reveal a range of culinary options.

Nearby regions

Best Bennington, VT lodging with a pool

Among the 80 accommodations in Bennington, VT, here are the 2 best ones with a pool

A Cozy Home Nestled In The Green Mountains Of Vermont! - Bennington, VT
8.8 3 reviews

A Cozy Home Nestled In The Green Mountains Of Vermont!

apartment, Pownal
This four-bedroom apartment is situated in Pownal, a peaceful rural area just 10 kilometres from Williamstown, offering easy access to its attractions. The apartment has received excellent user ratings and is perfect for families or groups of up to seven people.
The property is comfortably furnished and includes a well-equipped kitchen, a fireplace, a garden, a terrace, and a swimming pool. Guests can enjoy a range of activities in the surrounding area, including hiking, skiing, and exploring local shops and restaurants.
24 Acre Southern Vermont Luxury Hilltop Retreat - Private Pool & Panoramic Views - Bennington, VT
10 1 review

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

apartment, Stamford
This expansive four-bedroom residence in Stamford offers a secluded hillside setting on 9.7 hectares with Green Mountain views, located 7 minutes from Mass MoCA and 32 kilometres from The Clark Art Institute and towns such as Wilmington and Williamstown.
This 418 square metre holiday home accommodates up to eight guests and features a swimming pool, terrace, fireplace, and bar area, providing an ideal base for outdoor pursuits including hiking, skiing at Mount Snow (35 kilometres) and Stratton (61 kilometres), and golf at Stamford Valley Golf Course.

Best Bennington, VT accommodations with a balcony

Vt Farmhouse Private, Peaceful And Beautiful - Bennington, VT
9.8 173 reviews

Vt Farmhouse Private, Peaceful And Beautiful

apartment, Shaftsbury
This charming gîte is situated in a peaceful rural setting just six miles from Arlington Town Forest, New Skete Monastery, and the Shaftsbury Historical Society Museum. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
This spacious two-bedroom holiday home can comfortably accommodate six guests and spans 209 square metres. The gîte features a fully equipped kitchen, a terrace, a garden, and parking, as well as air conditioning and internet access, making it ideal for families and groups looking for a relaxing and enjoyable stay.
Cozy A-frame With Loft Views! - Bennington, VT
No reviews

Cozy A-frame With Loft Views!

cabin, Pownal
This secluded A-frame lodge in Pownal, Vermont, offers an 'off-the-grid' experience at the end of a private dirt road, situated approximately 9.6 kilometres from the Clark Art Institute in Williamstown, Massachusetts, and Hoosick Falls, New York.
This family-friendly accommodation for up to five guests boasts two bedrooms, one bathroom, a full kitchen, air conditioning, Wi-Fi, and a garden, with easy access to hiking, skiing, and other Green Mountain activities.
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins To Williamstown - Bennington, VT
10 34 reviews

Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins To Williamstown

apartment, Pownal
This three-bedroom apartment is situated in Pownal, Vermont, just five minutes from Williams College and a 27-kilometre drive to Jiminy Peak ski resort, offering a tranquil escape in the scenic countryside. This property has received excellent guest reviews, indicating a high standard of comfort and service.
The apartment spans 167 square metres and comfortably accommodates up to eight guests. It features a fully equipped kitchen, a fireplace, a Jacuzzi, a garden, parking, high-speed internet, and access to a private 45-acre estate with direct access to the Mountain Meadow Preserve, offering a range of outdoor activities such as swimming, fishing, hiking, and birdwatching.
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, situated in the town centre, offers easy walking access to Historic Old Bennington and its amenities, with major highways and nearby ski resorts also conveniently accessible.
The third-floor flat features a high-vaulted ceiling, a private balcony with Mount Anthony and the Bennington Monument views, accommodating two guests with one bedroom, one bathroom, fiber Wi-Fi, and Chromecast with YouTube TV.
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