Find short term rentals in Bennington, VT at the best prices
31 available short term rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Short term and Weekly rentals in Bennington, VT
9.4 69 reviews
Bennington, VT
01/07 – 08/07
$321/nighttotal: $2247 (7 )
Spacious & Spectacular Master Suite
1 1
apartment , Bennington
This charming bed and breakfast is situated in Old Bennington, a short walk from the Bennington Battle Monument and Robert Frost’s grave, and a short drive from Bennington College and downtown Bennington. It has received excellent ratings for its location, cleanliness, and overall experience. The property offers a spacious master bedroom suite with a private bathroom featuring a jacuzzi bath and separate shower, and guests have access to the entire house, including a chef’s kitchen, music room with two grand pianos, fireplaces, a screened porch, and an outdoor grill. The three-acre grounds offer opportunities for outdoor activities like cycling, with maps provided for local routes.
9.7 27 reviews
Bennington, VT
05/10 – 07/10
$455/nighttotal: $910 (2 )
Green Mountain Getaway
3 2
apartment , Bennington
This Bennington apartment is situated less than 1.6km from Green Mountain National Forest, Bennington Potters Yard, and Fiddlehead at Four Corners, offering easy access to local attractions. This three-bedroom property boasts 135 square metres of floor space, sleeping up to six guests and including a fully equipped kitchen, in-unit laundry, free parking, and complimentary Wi-Fi.
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.
9.3 15 reviews
Bennington, VT
08/08 – 09/08
$282/nightfor 1 night
Woodford Rest
2 4
aparthotel , Woodford
Woodford Rest, situated in Woodford, Vermont, is conveniently located within 16 kilometres of the Bennington Battle Monument and Bennington Museum. This family-friendly motel offers 46 square metre rooms, sleeping up to seven guests, each with a private bathroom, fridge, microwave, air conditioning, and access to a garden and free parking; nearby attractions include the Clark Art Institute (35km) and Mount Equinox (48km).
9.9 156 reviews
Bennington, VT
01/07 – 08/07
$287/nighttotal: $2009 (7 )
The Hubbell Barn In Bennington Vt East Room
1 1
house , Bennington
The Hubbell Homestead barn suites are situated on the west side of Bennington, just a short drive from the Bennington Battle Monument and the historic downtown area. The property has received excellent ratings for its location, cleanliness, and overall experience. Each suite at the Hubbell Homestead can accommodate two guests and features a king-sized bed, a private bathroom with a walk-in shower and Jacuzzi tub, and a cosy sitting area. Guests can enjoy a shared kitchenette, a large wrap-around porch, and a range of amenities including plush bathrobes, clean linens, Wi-Fi, and cable TV.
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.
10 9 reviews
Bennington, VT
05/10 – 07/10
$505/nighttotal: $1010 (2 )
Vermont Downtown Oasis - Two Bedroom In Picturesque Downtown
2 2
apartment , Bennington
This Bennington apartment, situated above Haberdasher Wine and Provisions in the town centre, is within walking distance of restaurants, shops, and breweries, and a short drive from the Green Mountain National Forest and several ski resorts including Mount Snow. The self-catering flat, occupying the entire second floor of a historic building on the state historic register, offers two bedrooms, one bathroom, and sleeps four, complete with a fully equipped kitchen including a fridge, microwave, and dishwasher, plus air conditioning, parking and internet access.
10 82 reviews
Bennington, VT
01/07 – 08/07
$503/nighttotal: $3521 (7 )
Dreamy & Stylish Log Cabin Near Town W/ Fast Wifi
1 1
apartment , Bennington
This log cabin is tucked away in the woods near Bennington, Vermont, less than an hour from the New York Thruway, 40 minutes from Mount Snow, 30 minutes from Manchester Center, and 30 minutes from Mass MOCA. This highly-rated property boasts excellent reviews for its location, cleanliness, and overall experience. The home has two bedrooms and two bathrooms, comfortably accommodating up to six guests. The property boasts modern amenities, including a fully-equipped kitchen, super-fast Wi-Fi, and a basement entertainment area with a pool table, pinball machine, darts, and ping pong table.
9.7 149 reviews
Bennington, VT
01/07 – 08/07
$216/nighttotal: $1512 (7 )
Bennington Village Home On Vt Rt.9
1 1
house , Bennington
This apartment is conveniently located just a short walk from Bennington's downtown area, offering easy access to the Bennington Museum and the historic Old First Church, while still enjoying a peaceful, quiet neighbourhood. Guests consistently rate the apartment excellent for cleanliness, location, and overall experience. The two-bedroom flat can comfortably accommodate up to six guests, making it a great option for families or groups of friends. The well-equipped kitchen includes a fridge, microwave oven, and dishwasher, while air conditioning and a ceiling fan keep the space cool and comfortable.
10 59 reviews
Bennington, VT
05/10 – 07/10
$515/nighttotal: $1030 (2 )
Awesome 3 Bedroom Apartment Close To It All
1 2
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.
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.
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.
Best family friendly Bennington, VT Short term rentals
Among the 31 accommodations in Bennington, VT, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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?
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
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.
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.
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.
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
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.
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.
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.
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.