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

1769 Henry House/tavern / Near Manchester - Bennington, VT
10 78 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.
Bennington Guest Farmhouse 5 Bedrooms - Bennington, VT
9.7 190 reviews

Bennington Guest Farmhouse 5 Bedrooms

apartment, Bennington
This Victorian farmhouse is located just a mile outside of Bennington, Vermont, making it a convenient base for exploring the town and surrounding countryside. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The farmhouse offers spacious accommodation for up to nine guests, with five bedrooms and two bathrooms spread across 251 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a terrace, a garden, and parking, as well as a gas fireplace and air conditioning for comfort.
Lake Life At Woodford Cottage - Bennington, VT
9.6 15 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.
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 lodging with a balcony

South Shire - Bennington, VT
9.1 334 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.
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.
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.

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

Escape The City- Vermont Studio - Bennington, VT
9.9 214 reviews

Escape The City- Vermont Studio

apartment, Bennington
This studio apartment is situated in the Green Mountain National Forest, just a short walk from the Mile Around Woods and a few kilometres from Bennington College. It has received excellent ratings for its location, cleanliness, and overall experience.
The self-catering studio has one bedroom and one bathroom and can accommodate up to two guests. It comes equipped with a kitchen, modern appliances, a private deck, and a range of amenities including high-speed Wi-Fi, a slack line, and a mini smoothie blender.
Suite Sunset
311 Rice Lane
Bennington Vt - Bennington, VT
9.9 112 reviews

Suite Sunset 311 Rice Lane Bennington Vt

apartment, Bennington
This Bennington apartment is situated on a private 50-acre property, less than 1.6 kilometres from Bennington College and close to the town centre.
The self-contained apartment offers a private entrance, spacious living areas, and a fully equipped kitchen, comfortably accommodating up to three guests.
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.
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.

Best Bennington, VT lodging with laundry available

A Charming 1800s Home In True Vermont Style. - Bennington, VT
10 2 reviews

A Charming 1800s Home In True Vermont Style.

B&B, Shaftsbury
This historic 1850s guesthouse in Shaftsbury offers refined wood craftsmanship and is conveniently located approximately 160 kilometres from Albany, and 48 kilometres from both Manchester and Wilmington, with three ski resorts within a 160-kilometre radius.
This Bed and Breakfast provides three guest rooms with air conditioning, internet access, a kitchen, and parking, accommodating up to two guests, and is ideal for those seeking ski breaks or exploring the surrounding areas.
Quiet Apartment Getaway - Bennington, VT
9.6 62 reviews

Quiet Apartment Getaway

apartment, Bennington
This Bennington apartment, ideally situated in southern Vermont, offers easy access to attractions in Vermont, New York, and Massachusetts.
The two-bedroom, one-bathroom flat sleeps five guests and boasts a fully equipped kitchen including a dishwasher, plus free parking and Wi-Fi; a unique birch forest wall feature adds character to this comfortable home-from-home.
Charming 2-bedroom Apartment In Superb Bennington With Wifi - Bennington, VT
9.8 7 reviews

Charming 2-bedroom Apartment In Superb Bennington With Wifi

apartment, Bennington
This Bennington apartment, ideally located near Bennington Potters Yard and Fiddlehead at Four Corners, offers easy access to Green Mountain National Forest and Lake Shaftsbury State Park, though precise distances aren't specified.
The 93 square metre (approx. 1000 sq ft) self-catering flat sleeps up to four guests comfortably in two bedrooms, with a queen, twin, and full bed, and includes a fully equipped kitchen with fridge, microwave, and dishwasher, plus WiFi, a washing machine, and on-site parking.
!Charming Cabin,  Great Views - Bennington, VT
9.5 190 reviews

!Charming Cabin, Great Views

cabin, Shaftsbury
This charming cabin is situated in Shaftsbury, Vermont, just 20-30 kilometres from Bennington and Manchester, offering a peaceful retreat in a rural setting. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The property spans 107 square metres and comfortably accommodates up to seven guests in its two bedrooms and one bathroom. Enjoy the modern conveniences, farm animal encounters, and outdoor activities, including hiking trails, a pond, and a fire pit.
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