Find short term rentals in Bennington, VT at the best prices
31 available short term rental offers
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Best Short term and Weekly rentals in Bennington, VT
8.5 27 reviews
Bennington, VT
01/07 – 08/07
$209/nighttotal: $1463 (7 )
Historic Downtown Apartment Near Skatepark
1 1
apartment , Bennington
This four-bedroom flat is located in downtown Bennington, Vermont, just a short walk from the new walking trail that connects to North Bennington and Main Street, where you'll find local restaurants and shops. The apartment can accommodate up to six guests and has a laundry/breezeway area, a kitchen with a fridge and microwave oven, and air conditioning. The apartment also has parking and internet access, making it a convenient and comfortable choice for your stay.
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.
9.9 35 reviews
Bennington, VT
01/07 – 08/07
$433/nighttotal: $3031 (7 )
Vermont🍁🌲
1 1
apartment , Bennington
This apartment is located just outside Bennington, within a couple of kilometres of shops and restaurants, offering a peaceful retreat in the woods. It consistently receives excellent ratings for its cleanliness, location, and overall experience. The apartment has three bedrooms and two bathrooms, comfortably accommodating up to four guests. It features a fully equipped kitchen, internet access, and a garden, making it an ideal choice for families or groups looking for a relaxing and convenient base in Bennington.
9.7 6 reviews
Bennington, VT
01/07 – 08/07
$302/nighttotal: $2114 (7 )
Large Country Ranch On 2 Acres
4 1
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.
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.
Bennington, VT
01/07 – 08/07
$198/nighttotal: $1386 (7 )
Knotty Pine Motel - King Suite W/kitchenette
1 1
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.
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.
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.
10 6 reviews
Bennington, VT
01/07 – 08/07
$157/nighttotal: $1099 (7 )
A Cozy Taste Of Vermont
1 1
apartment , Bennington
This Bennington flat offers easy access to downtown, located just a short walk from local amenities. This one-bedroom flat accommodates two guests and features a kitchen, air conditioning, internet, parking, and a gaming system, with unique design considerations for guests of mid-size stature.
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.
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.
9.9 95 reviews
Bennington, VT
01/07 – 08/07
$187/nighttotal: $1309 (7 )
Cozy Loft Steps From Vt Downtown
1 1
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.
Best family friendly Bennington, VT Short term rentals
Among the 31 accommodations in Bennington, VT, here are the 4 best family friendly rentals
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.
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.
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.
9.7 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
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.
8.9 557 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?
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.
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.
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.
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
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.
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.
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.
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.