Find short term rentals in Bennington, VT at the best prices

41 available short term rental offers

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Bennington, VT short term rentals
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Best Short term and Weekly rentals in Bennington, VT

Best family friendly Bennington, VT Short term rentals

Among the 41 accommodations in Bennington, VT, here are the 4 best family friendly rentals

Memes High Mountain Lake House - Bennington, VT
9.8 102 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.
"The Triple Chambers" - Bennington, VT
9.8 110 reviews

"The Triple Chambers"

apartment, Pownal
This charming apartment is located in Pownal, Vermont, just a short distance from Williamstown, Massachusetts, home to Williams College, the Williamstown Theatre Festival, and the Clark Art Museum. The apartment enjoys excellent ratings for location, cleanliness, and overall user experience.
This second-floor flat offers a private entrance and features a unique curved staircase. Guests can enjoy a fully equipped kitchen, Wi-Fi, satellite TV, outdoor seating, a chiminea, and a BBQ area.
Sold. Not Taking Any Stays - Bennington, VT
9.3 21 reviews

Sold. Not Taking Any Stays

apartment, 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.
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.

Best Bennington, VT lodging with a balcony

Mid Century Modern  4 Bedroom Home With Sweeping Mountain Views In Williamstown - Bennington, VT
9.8 16 reviews

Mid Century Modern 4 Bedroom Home With Sweeping Mountain Views In Williamstown

apartment, Williamstown
This Williamstown apartment, a 13-minute walk (approx. 2.1km) from Green Mountain National Forest and an 8-minute drive (approx. 6.4km) from Buxton Gardens, offers convenient access to local attractions. This four-bedroom, two-bathroom property sleeps seven guests and includes amenities such as Wi-Fi, parking, a fully equipped kitchen with dishwasher, and an outdoor barbecue.

Frequently Asked Questions about short term rentals in Bennington, VT

  • Can visitors to Bennington, Vermont witness any unique natural cycles, like cherry blossom season or autumn colors?

    Absolutely! Bennington experiences vibrant autumn foliage typically peaking in mid-October. While cherry blossoms aren't as prominent as in some other regions, you'll find beautiful spring blooms throughout the area. The changing leaves in the fall are a major draw, transforming the Green Mountains into a breathtaking spectacle.
  • What are the best short term rentals in Bennington, VT?

    Among the short term rentals in Bennington, VT, Romantic Private Vermont Cottage - Waterfront, Scenic Vermont Studio and Cooper's Place are the most popular ones.

  • What are the most meaningful ways to engage with locals and discover the culture in Bennington, Vermont?

    To connect with the local culture, visit the Bennington Farmers' Market to meet producers and sample local goods. Attend a performance at the Oldcastle Theatre Company or a concert at the Bennington Performing Arts Center. Strike up conversations with staff at local shops and restaurants; many are long-time residents. Consider exploring the historical sites and learning about the town's rich history.
  • What are the best short term rentals for families and kids in Bennington, VT?

  • Are there any distinctive cultural activities or hands-on workshops in Bennington, Vermont?

    Bennington offers various cultural activities. The Bennington Museum frequently hosts workshops and events. Check their calendar for pottery classes, art demonstrations, or historical talks. The area also has several craft studios and artisan shops where you might find workshops or demonstrations. Many local farms offer seasonal activities like apple picking or maple sugaring demonstrations.
  • What are some secret spots or hidden treasures to visit in Bennington, Vermont?

    While Bennington doesn't have many truly 'secret' spots, some lesser-known gems include the smaller hiking trails branching off from the main paths in the Green Mountain National Forest. Explore the backroads to find charming country stores and antique shops. The local libraries often have hidden collections or historical documents worth exploring.
  • What should not be left out of your suitcase if you are going to Bennington, Vermont?

    Pack comfortable walking shoes for exploring the town and hiking trails. Layers of clothing are essential, as the weather in Vermont can change quickly. Don't forget a rain jacket, even during summer months. A good book is always a plus for those quiet moments. And of course, a camera to capture the stunning scenery.
  • Where should one try the best local food in Bennington, Vermont?

    For a taste of local fare, try the Walloomsac Inn for upscale dining or the Four Chimneys Inn for a more casual atmosphere. Several smaller cafes and restaurants in downtown Bennington also offer delicious local options. Exploring the Bennington Farmers' Market is a great way to sample local produce and baked goods.

Nearby regions

Best Bennington, VT lodging with a kitchen

Brand-new, Private 3-bed Mountain Retreat W/ Hiking Trails, Hot Tub, Fire Pit! - Bennington, VT
10 7 reviews

Brand-new, Private 3-bed Mountain Retreat W/ Hiking Trails, Hot Tub, Fire Pit!

apartment, Pownal
This new mountain retreat in Pownal, Vermont, offers rural seclusion just a short drive from Williams College, the Williamstown Theatre Festival, and the Clark Art Institute.
This three-bedroom flat accommodates up to six guests and features a brand-new kitchen with state-of-the-art appliances, a hot tub, and is conveniently located 8 kilometres from Williams College, providing easy access to ski resorts and Bennington.
Quiet, Cozy, Conveniently Located - Bennington, VT
No reviews

Quiet, Cozy, Conveniently Located

apartment, Shaftsbury
This one-bedroom flat in Shaftsbury, Southern Vermont, offers a prime location for exploring the region's year-round attractions, including skiing and hiking opportunities.
This stylish apartment accommodates two guests and features a kitchen and internet, serving as an excellent base for outdoor enthusiasts and those seeking a comfortable and memorable stay.
Historic Apt. Close To Downtown Bennington - Bennington, VT
8.5 29 reviews

Historic Apt. Close To Downtown Bennington

apartment, Bennington
This four-bedroom flat is located in downtown Bennington, Vermont, just a short walk from the new walking trail that connects to North Bennington and Main Street, where you'll find local restaurants and shops.
The apartment can accommodate up to six guests and has a laundry/breezeway area, a kitchen with a fridge and microwave oven, and air conditioning. The apartment also has parking and internet access, making it a convenient and comfortable choice for your stay.
Farm-to-table Eating, Good Hot Tub Soak, S'mores Around Fire Pit, Seasonal Pool! - Bennington, VT
9.4 90 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.

Best Bennington, VT lodging with laundry available

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.
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.
E And Es B And B Queen Bed Rm+ Pool & Hot Tub - Bennington, VT
10 139 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.
Lake Life At Woodford Cottage - Bennington, VT
9.6 16 reviews

Lake Life At Woodford Cottage

cottage, Woodford
This Bennington cottage is located just 1.4 miles from the Prospect Mountain Nordic Ski Center, with other attractions like the Prospect Mountain Cross-Country Ski Center and Harmen Hills Trail within easy reach. The cottage has received excellent ratings for its location, cleanliness and overall user experience.
The two-bedroom cottage has one bathroom and a comfortable living space. Guests can enjoy a garden, barbecue grills, a fireplace, a fully equipped kitchen and free WiFi.
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