Places to stay in Bennington, VT

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Bennington, VT place to stay
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80 Best places to stay in Bennington, VT

Best family friendly Bennington, VT lodging

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

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

The Cozy Cottage @ Woodford Lake

apartment, Woodford
This charming cottage is situated on the shores of Woodford Lake, just a short drive from the town centre and within easy reach of the surrounding hills. The cottage has received excellent ratings for its cleanliness, location and overall experience, making it a popular choice for families and groups.
The cottage offers three bedrooms and one bathroom, comfortably accommodating up to five guests. Enjoy stunning lake views, a cosy living room with a gas fireplace, a fully equipped kitchen, and a private outdoor space perfect for relaxing and enjoying the fresh air.
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.
Cozy Getaway In Woodford - Bennington, VT
10 6 reviews

Cozy Getaway In Woodford

cabin, Woodford
This Woodford lodge is located in a mountain setting, directly across Route 9 from Prospect Mountain for winter activities and 48 kilometres from Mount Snow for skiing.
Accommodating up to seven guests across three bedrooms, this family-friendly cottage offers a well-equipped kitchen, a spacious living area with a fireplace, and amenities including a washer, dryer, and Wi-Fi.
Sold. Not Taking Any Stays - Bennington, VT
9.3 21 reviews

Sold. Not Taking Any Stays

house, Bennington
This five-bedroom home is located in a friendly neighbourhood in Bennington, just a short drive from the town centre and the Bennington Museum. The property has consistently received excellent ratings for its cleanliness, location and overall experience.
This spacious house can comfortably accommodate up to seven guests and features a large living area, a well-equipped kitchen, a charming three-season porch and a large deck with a barbecue grill. Guests can enjoy access to a shared garden, a fitness centre, parking and a wood-burning stove.

Best Bennington, VT accommodations with a kitchen

The Crik House: Modern Digs, American Farm Country - Bennington, VT
10 44 reviews

The Crik House: Modern Digs, American Farm Country

apartment, Hoosick Falls
The Crik House, a newly renovated self-catering property in White Creek's historic farming district, is situated 8 minutes from Bennington College and 15 minutes (approx. 13 and 24 km respectively) from the Southwestern Vermont Medical Center.
This single-storey holiday home, sleeping four in two bedrooms and one bathroom, boasts a Scandinavian-modern design, high-speed internet, a fully equipped kitchen, EV charging, and is within walking distance of the White Creek Country Store; accessibility features include a low-threshold entry and walk-in shower.
Cozy Loft Steps From Vt Downtown - Bennington, VT
9.9 101 reviews

Cozy Loft Steps From Vt Downtown

apartment, Bennington
This one-bedroom loft apartment in Bennington is located within walking distance of the historic Old Bennington district, offering easy access to shops, restaurants, and historical landmarks. The apartment features a private balcony with views of Mount Anthony and the Bennington Monument, as well as a spacious living area with high vaulted ceilings and a large bay window.
Serene Getaway In The Vermont National Forrest - Bennington, VT
9.4 10 reviews

Serene Getaway In The Vermont National Forrest

apartment, Woodford
This four-bedroom apartment is located near Williamstown, Vermont, just a short distance from the Appalachian Trail, MASS MOCA, the Clark Art Museum, the Williamstown Summer Theater, and a world-class Nordic centre. The apartment has received excellent user and location ratings, and a very good cleanliness rating.
The property is a spacious home with two bathrooms, suitable for up to eight guests. The apartment comes with a fully equipped kitchen, a Jacuzzi, a garden, a sauna, parking, and internet access, making it ideal for families or groups seeking a relaxing and comfortable stay.
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.

Frequently asked questions about accommodations in Bennington, VT

  • What are the most characteristic landscapes and terrains found in Bennington, Vermont?

    Bennington's landscape is characterised by rolling hills, typical of Vermont's Green Mountains. Expect to see lush forests, picturesque farmland, and the dramatic presence of Mount Anthony, offering stunning views of the surrounding area. The terrain is generally hilly, so be prepared for some inclines if you plan on exploring on foot or by bicycle.
  • What are the best accommodations in Bennington, VT?

    Among the accommodations in Bennington, VT, Hampton Inn Bennington, Hotel Vervana - Trademark Collection By Wyndham and Harwood Hill Motel are the most popular ones.

  • What are the best outdoor activities in Bennington, Vermont?

    Hiking and mountain biking trails abound around Mount Anthony. There are also opportunities for scenic drives along the many country roads, offering breathtaking views. Exploring the numerous hiking trails in the Green Mountain National Forest, which borders Bennington, is another popular outdoor activity.
  • What are the best accommodations with a pool in Bennington, VT?

    Hampton Inn Bennington, Hotel Vervana - Trademark Collection By Wyndham and Best Western Bennington are the best accommodations with a pool in Bennington, VT.

  • What is the best time of year to visit Bennington, Vermont with kids?

    Summer (June to August) offers the warmest weather, ideal for outdoor activities like hiking and exploring the town. Autumn (September to October) provides stunning foliage, creating a picturesque backdrop for family outings and scenic drives. However, be aware that some attractions may have limited hours outside of peak season.
  • What are the best accommodations with a jacuzzi in Bennington, VT?

    The best accommodations with a jacuzzi in Bennington, VT are Hampton Inn Bennington, South Shire and E And E’s B And B Queen Bed Rm+ Pool & Hot Tub.

  • Are there local customs to be aware of in Bennington, Vermont?

    Bennington is a friendly and welcoming town. There aren't any specific unusual local customs to be overly concerned about. However, as with any small town, a polite and respectful attitude towards residents and their surroundings is always appreciated.
  • What are the best accommodations for families and kids in Bennington, VT?

    The best accommodations for families and kids in Bennington, VT are Four Chimneys Inn, South Shire and Knotty Pine Motel.

  • What are the best ways to interact with locals and learn about their culture in Bennington, Vermont?

    Visiting local businesses, such as the many independent shops and restaurants in the town centre, is a great way to interact with residents. Attending local events, like the Bennington Battle Day Parade, provides an opportunity to engage with the community and experience the town's spirit. Striking up conversations with people at local establishments is generally well-received.
  • What are the best pet friendly accommodations in Bennington, VT?

    The best pet friendly accommodations in Bennington, VT are Hampton Inn Bennington, Hotel Vervana - Trademark Collection By Wyndham and Harwood Hill Motel.

  • What are some lesser-known attractions or hidden gems in Bennington, Vermont?

    The Monument Hill area, while not entirely unknown, is often overlooked. It offers lovely walking trails and a quieter, more secluded experience compared to the more prominent attractions. Exploring the smaller, independent shops and art galleries dotted around the town can also uncover some unexpected gems.
  • What are the best accommodations with parking in Bennington, VT?

    Hampton Inn Bennington, Hotel Vervana - Trademark Collection By Wyndham and Harwood Hill Motel are the best accommodations with parking in Bennington, VT.

  • What are some must-try local dishes in Bennington, Vermont?

    Vermont is known for its maple syrup, so trying pancakes or waffles drenched in local maple syrup is a must. Many restaurants in Bennington serve classic New England fare, including hearty stews and locally sourced meats. Look for restaurants featuring Vermont cheddar cheese in their dishes – it's a local favourite.

Nearby regions

Best Bennington, VT lodgings with a pool

Among the 80 accommodations in Bennington, VT, here are the 3 best ones with a pool

Private Indoor Heated Pool + Hot Tub + Fire Pit + Pond, On 35 Acres - Sleeps 20 - Bennington, VT
9.4 9 reviews

Private Indoor Heated Pool + Hot Tub + Fire Pit + Pond, On 35 Acres - Sleeps 20

apartment, Hoosick Falls
This six-bedroom property is situated in Hoosick Falls, a short drive from the Berkshires and Vermont Mountains, offering a peaceful escape in the scenic countryside. The property has received excellent reviews from previous guests.
The spacious home can accommodate up to 20 guests, making it perfect for large families or groups of friends. Guests can enjoy a range of amenities, including an indoor heated pool and hot tub, a game room, a fishing pond, and a fire pit, ensuring a comfortable and entertaining stay.
Vt Hilltop Retreat, Views, Fireplace, Near Mt Snow - Bennington, VT
No reviews

Vt Hilltop Retreat, Views, Fireplace, Near Mt Snow

apartment, Stamford
This southern Vermont hilltop lodge offers panoramic Green Mountain views, situated 35 kilometres from Mount Snow and close to Stratton, hiking trails, and the Massachusetts Museum of Contemporary Art.
This 418 square metre holiday home features 3 bedrooms, a bonus sleeping room, and a capacity for 8 guests, with amenities including a private in-ground swimming pool, a floor-to-ceiling stone fireplace, a den with a bar, and fast WiFi.
Artist Bunkhouse Southern Vermont - Bennington, VT
9.9 98 reviews

Artist Bunkhouse Southern Vermont

farm, Pownal
This Pownal, Vermont bunkhouse-style guesthouse, situated above a working pottery studio, offers four private bedrooms, a fully equipped kitchen, and a shared entrance with a full-time tenant, but completely private guest spaces (kitchen, bathroom).
Sleeping eight guests, this self-catering property boasts a swimming pool, garden, parking, and excellent user, location, and cleanliness ratings; guests can also enjoy private pottery classes from the owner.

Best Bennington, VT accommodations with a balcony

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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