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

Private Home On 37 Acres With Stunning Mountain Views - Bennington, VT
9.3 32 reviews
Bennington, VT
27/06 – 29/06
$2548/nighttotal: $5096 (2 )

Private Home On 37 Acres With Stunning Mountain Views

5 2
apartment , Shaftsbury
This private house is located in Shaftsbury, Vermont, just 18 kilometres from the Bennington Battle Monument and 67 kilometres from Albany International Airport. The property has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The five-bedroom property can accommodate up to twelve guests, offering ample space for families or groups. Guests can enjoy a range of amenities, including a fully equipped kitchen, a terrace with a barbecue, a jacuzzi, a spa, a tennis court, a garden, and free parking and Wi-Fi.
South Shire - Bennington, VT
8.9 605 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.
Quiet Apartment Getaway - Bennington, VT
9.7 55 reviews
Bennington, VT
05/10 – 07/10
$231/nighttotal: $462 (2 )

Quiet Apartment Getaway

1 2
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
Bennington, VT
05/10 – 07/10
$230/nighttotal: $460 (2 )

Charming 2-bedroom Apartment In Superb Bennington With Wifi

2 2
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.

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
8.9 605 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 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 Retreat In Heart Of Town - Bennington, VT
9.9 111 reviews
Bennington, VT
05/10 – 07/10
$286/nighttotal: $572 (2 )

Modern Retreat In Heart Of Town

1 2
apartment , Bennington
This Bennington apartment, a short walk from the town centre and close to The Blue Benn diner, offers easy access to Bennington's amenities and the local bike path.
The two-bedroom, one-bathroom flat sleeps four, features a fully equipped kitchen with high-top table, king-size and twin beds, ample storage, a three-season porch with mountain views, and private off-street parking.
Vermont Downtown Oasis - Bennington, VT
10 78 reviews
Bennington, VT
05/10 – 07/10
$502/nighttotal: $1004 (2 )

Vermont Downtown Oasis

1 2
apartment , Bennington
This Bennington apartment, a luxurious conversion of a historic building on the state register, enjoys a prime downtown location, within walking distance of restaurants and shops, and a short drive (approximately 30-60 km depending on the resort) from Mount Snow, Bromley, Stratton, and Prospect Mountains.
The two-bedroom, one-bathroom flat offers guests the entire top floor, sleeping up to four, and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, parking, and excellent guest reviews.

Best Bennington, VT lodging with laundry available

Comfy Private Large Suite W/kitchen Access Option - Bennington, VT
10 6 reviews
Bennington, VT
05/10 – 07/10
$189/nighttotal: $378 (2 )

Comfy Private Large Suite W/kitchen Access Option

1 2
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.
The Old Pine House - Bennington, VT
10 56 reviews
Bennington, VT
05/10 – 07/10
$499/nighttotal: $998 (2 )

The Old Pine House

1 2
apartment , Bennington
This renovated 1830s house is centrally located in downtown Bennington, Vermont, within walking distance of shops, restaurants, a dispensary, and a brewery.
This 2,000 square foot property boasts three bedrooms, two bathrooms, and sleeps six, featuring an updated kitchen with modern appliances, in-house laundry, and spacious porches.
Cozy Loft Steps From Vt Downtown - Bennington, VT
9.9 95 reviews
Bennington, VT
05/10 – 07/10
$339/nighttotal: $678 (2 )

Cozy Loft Steps From Vt Downtown

1 2
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.
Walkable Modern 2br In Downtown - Right Unit - Bennington, VT
9.8 60 reviews
Bennington, VT
01/07 – 08/07
$210/nighttotal: $1470 (7 )

Walkable Modern 2br In Downtown - Right Unit

1 1
apartment , Bennington
This two-bedroom flat is situated in a central Bennington neighbourhood, just a short walk from Walmart, Hannaford, and other shops, making it a convenient base for exploring the area. The flat has consistently received excellent ratings for its location, cleanliness, and overall experience.
The flat comfortably sleeps up to six guests and features a well-equipped kitchen with a fridge and freezer. Amenities include air conditioning, a garden, parking, and free Wi-Fi, allowing you to relax and enjoy your stay.
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