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

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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

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.
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.
1769 Henry House/tavern / Near Manchester - Bennington, VT
10 79 reviews

1769 Henry House/tavern / Near Manchester

apartment, Bennington
The Henry House is a historic home situated on 25 acres of meadows and mountains, overlooking the Walloomsac River and the Henry Covered Bridge, a short distance from Bennington's historic downtown area. This property has received excellent ratings for its location, cleanliness and overall experience.
The house has a variety of rooms, including a cozy first-floor room, a grand ballroom/bridal suite, and a spacious upstairs room with exposed woodwork, accommodating up to 10 guests. Amenities include a fully equipped kitchen, a garden, parking, and a private bathroom for several rooms.
Awesome 3 Bedroom Apartment Close To It All - Bennington, VT
10 62 reviews

Awesome 3 Bedroom Apartment Close To It All

apartment, Bennington
This three-bedroom apartment is located above The Elm Street Market in downtown Bennington, putting you within easy walking distance of restaurants, historical sights, and the town centre. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
The flat has a spacious living room, a well-equipped kitchen, and a three-season porch, comfortably accommodating up to five guests. You'll have access to a range of modern amenities, including Wi-Fi, a smart TV, and a gourmet deli downstairs, offering everything from breakfast sandwiches to gourmet espresso.

Best Bennington, VT lodging with a balcony

Spacious Mountain Retreat With Hot Tub, Fire Pit & Hiking Trails - Bennington, VT
10 27 reviews

Spacious Mountain Retreat With Hot Tub, Fire Pit & Hiking Trails

apartment, Pownal
This Pownal holiday home boasts a mountainside location, situated within 3.2km of the Green Mountain National Forest and 3.9km from the Solomon Wright Public Library.
The 223 square metre property sleeps 12 guests in four bedrooms and two bathrooms, offering a fitness centre, tennis court, Jacuzzi, and a fully equipped kitchen alongside free Wi-Fi; enjoy stunning views and easy access to outdoor activities.
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.
A Cozy Home Nestled In The Green Mountains Of Vermont! - Bennington, VT
9.0 4 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.
South Shire - Bennington, VT
9.1 343 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.

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

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.
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.
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.
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 lodging with laundry available

Large Country Ranch On 2 Acres - Bennington, VT
9.7 6 reviews

Large Country Ranch On 2 Acres

apartment, Bennington
This charming four-bedroom house is located in Bennington, Vermont, just an hour from Saratoga Springs and its horse races, and within easy reach of ski resorts like Mt. Snow and Bromley Mountain. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The house features a spacious living area with a fireplace, a large wraparound deck with stunning mountain views, and a fully equipped kitchen. Guests can enjoy a range of amenities, including WiFi, a laundry room, a large parking lot, and easy access to various outdoor activities like skiing, hiking, and horse shows in nearby towns.
Mountain Sanctuary Dome Rustic Solitude 5br - Bennington, VT
9.8 11 reviews

Mountain Sanctuary Dome Rustic Solitude 5br

apartment, Bennington
This five-bedroom Pownal house, perfect for large groups, is situated near Green Mountain National Forest, with Taconic Ridge State Forest and Southern Vermont College within 9.6km.
Sleeping up to 12 guests, this property boasts two bathrooms, a fully equipped kitchen including a fridge and stovetop, free Wi-Fi, a terrace, garden, parking, and on-site barbecue grills; enjoy the in-house fireplace and proximity to outdoor activities.
< 1 Mi To Historic District! Retreat In Bennington - Bennington, VT
9.4 7 reviews

< 1 Mi To Historic District! Retreat In Bennington

apartment, Bennington
This holiday home in Bennington, Vermont is conveniently located just a short drive from the Bennington Museum, the Robert Frost Trailhead, and the Bradford Putnam Wetlands. Enjoy the peace and quiet of the surrounding area, with easy access to local attractions.
The property has one bedroom and one bathroom, comfortably accommodating up to four guests. Enjoy the well-equipped kitchen, dedicated workspace, mountain views, and outdoor seating, perfect for a relaxing 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.
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