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

31 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 31 accommodations in Bennington, VT, here are the 4 best family friendly rentals

1920's Bennington Vermont Guest Barn - Bennington, VT
9.6 201 reviews
Bennington, VT
01/07 – 08/07
$274/nighttotal: $1918 (7 )

1920's Bennington Vermont Guest Barn

1 1
apartment , Bennington
This spacious apartment is situated in a peaceful rural setting just outside Bennington, Vermont, within easy reach of the Bennington Museum and Robert Frost Museum, and a short drive from popular ski resorts. It enjoys excellent ratings for location, cleanliness, and overall user experience.
The apartment has three bedrooms and one bathroom, spanning 90 square metres and comfortably accommodating up to seven guests. It comes equipped with a range of modern amenities, including a fully equipped kitchen, a private terrace and garden, and a spa, offering everything you need for a relaxing and enjoyable stay.
South Shire - Bennington, VT
8.9 557 reviews
Bennington, VT
01/07 – 08/07
$360/nighttotal: $2520 (7 )

South Shire

1 1
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.
North Bennington, Vt Conveniently Located Unit. - Bennington, VT
9.7 81 reviews
Bennington, VT
01/07 – 08/07
$175/nighttotal: $1225 (7 )

North Bennington, Vt Conveniently Located Unit.

1 1
apartment , Bennington
This ground-floor flat is located in the quiet town of North Bennington, just a short walk from the Park McCullough Mansion and less than 1.6km from Bennington College. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
The flat is fully furnished and can accommodate up to four guests, making it perfect for families or groups of friends. Enjoy the peace and quiet of the private patio with a fire pit, explore the nearby lake with the provided kayak, or take advantage of the convenient proximity to local restaurants, shops, and attractions.
Walkable Modern 2br In Downtown - Left Unit - Bennington, VT
9.7 49 reviews
Bennington, VT
01/07 – 08/07
$229/nighttotal: $1603 (7 )

Walkable Modern 2br In Downtown - Left Unit

1 1
apartment , Bennington
This Bennington apartment is conveniently located just a short distance from supermarkets like Walmart and Hannaford, as well as a range of shops, making it easy to pick up essentials and explore the local area. The surrounding area also offers opportunities for outdoor recreation, with ski areas, mountains, hiking trails and lakes all within easy reach.
This comfortable self-catering property is ideal for families or groups of up to six people. The apartment has a kitchen with a fridge, freezer and microwave oven, as well as air conditioning, parking, and internet access.

Best Bennington, VT lodging with a balcony

Cozy Loft Steps From Vt Downtown - Bennington, VT
9.6 5 reviews
Bennington, VT
01/07 – 08/07
$202/nighttotal: $1414 (7 )

Cozy Loft Steps From Vt Downtown

1 1
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.
South Shire - Bennington, VT
8.9 557 reviews
Bennington, VT
01/07 – 08/07
$360/nighttotal: $2520 (7 )

South Shire

1 1
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

Leslie’s Bright & Cozy: King Room - Bennington, VT
9.9 125 reviews
Bennington, VT
01/07 – 08/07
$127/nighttotal: $889 (7 )

Leslie’s Bright & Cozy: King Room

1 1
apartment , Bennington
This charming guesthouse is located just 5 kilometres from Bennington town centre, making it ideal for exploring the area's historical landmarks, bustling shops, and restaurants. The property also enjoys easy access to outdoor activities like skiing at Stratton Mountain, hiking on the Long Trail, and cross-country skiing at Prospect Mountain. It has received excellent ratings for its location, cleanliness and overall experience.
The guesthouse has a private King Room, a full kitchen, dining room, living room, and two decks. Guests can also enjoy the benefits of a fitness centre, a garden, and a pet-friendly environment.
< 1 Mi To Historic District! Retreat In Bennington - Bennington, VT
10 1 review
Bennington, VT
01/07 – 08/07
$302/nighttotal: $2114 (7 )

< 1 Mi To Historic District! Retreat In Bennington

1 1
apartment , Bennington
This charming flat is situated in Bennington, just a short walk from Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and a 14.5km drive from Bennington Potters Yard. The area is known for its car enthusiasts and pottery lovers, offering a unique blend of modern and historical attractions.
The apartment spans 93 square metres and comfortably accommodates up to 4 guests, with one bedroom and one bathroom. It comes equipped with a kitchen, a washing machine, a dryer, and free parking, ensuring a comfortable and convenient stay.
Charming 2-bedroom Suite In Old Bennington - Bennington, VT
10 1 review
Bennington, VT
01/07 – 08/07
$464/nighttotal: $3248 (7 )

Charming 2-bedroom Suite In Old Bennington

1 1
apartment , Bennington
This charming bed and breakfast is situated in a peaceful residential area of Bennington, just a short walk from the Bennington Museum and a few minutes' drive from the historic Old First Church. It consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The property offers a private upstairs suite for up to four guests, providing a comfortable and independent space. Guests have access to a fully equipped kitchen, a cosy living room with a fireplace, a music room, an outdoor deck with a barbecue and fire pit, a screened-in porch, and a spacious garden.
< 1 Mi To Historic District! Retreat In Bennington - Bennington, VT
9.4 7 reviews
Bennington, VT
01/07 – 08/07
$238/nighttotal: $1666 (7 )

< 1 Mi To Historic District! Retreat In Bennington

1 1
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.

Best Bennington, VT lodging with laundry available

Holly's Retreat - Bennington, VT
9.9 27 reviews
Bennington, VT
01/07 – 08/07
$171/nighttotal: $1197 (7 )

Holly's Retreat

1 1
apartment , Bennington
This Bennington guesthouse is ideally situated near the town centre, a short 1.6km walk from the Manchester Athletic Club golf course and within easy reach of Old Bennington's historic sites and the Bennington Museum.
Offering a one-bedroom, one-bathroom suite sleeping two guests, this property features a private deck, fire pit, gas grill, and excellent access to local hiking, kayaking, and skiing at resorts such as Mount Snow, Bromley, and Stratton Mountain, all within an hour's drive.
1 Bedroom Guest House On Dead-end Rd - Bennington, VT
9.6 127 reviews
Bennington, VT
01/07 – 08/07
$190/nighttotal: $1330 (7 )

1 Bedroom Guest House On Dead-end Rd

1 1
apartment , Bennington
This one-bedroom flat is situated in a peaceful residential area in Bennington, just 5km from the Southwestern VT Medical Center, 40km from Mount Snow, 25km from MassMoca, and a 15-minute walk from the town centre. Guests consistently rate the apartment highly for its cleanliness, location, and overall experience.
The self-contained flat has a private patio and can accommodate up to two guests. Amenities include a fully equipped kitchen, on-site parking, and easy access to a range of attractions in the surrounding area.
Modern Rustic Hideaway In Town - Bennington, VT
10 96 reviews
Bennington, VT
01/07 – 08/07
$215/nighttotal: $1505 (7 )

Modern Rustic Hideaway In Town

1 1
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.
Comfy Private Large Suite W/kitchen Access Option - Bennington, VT
10 6 reviews
Bennington, VT
01/07 – 08/07
$162/nighttotal: $1134 (7 )

Comfy Private Large Suite W/kitchen Access Option

1 1
apartment , Bennington
This Bennington guesthouse offers budget-friendly single occupancy in a private room with en-suite bathroom (a short walk from the bedroom), featuring a fridge and microwave.
The property includes parking, air conditioning, Wi-Fi, and a porch; small dogs are present.
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