Bennington holiday rentals: compare the best deals
9.3 32 reviews
Bennington
06/27 – 06/29
HK$14285/nightTotal: HK$28570 (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.
10 6 reviews
Bennington
07/01 – 07/08
HK$880/nightTotal: HK$6160 (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.
9.9 35 reviews
Bennington
07/01 – 07/08
HK$2428/nightTotal: HK$16996 (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.
9.8 52 reviews
Bennington
10/05 – 10/07
HK$2120/nightTotal: HK$4240 (2 )
Green Mountain Getaway
1 2
apartment , Bennington
The Green Mountain Getaway is a three-bedroom house in Bennington, Vermont, offering easy access to Bennington's museums and the Green Mountains' hiking trails, distances varying depending on the precise location within the town. This self-catering property sleeps six, boasting a fully equipped kitchen with fridge, microwave, and dishwasher, plus a washing machine, air conditioning, Wi-Fi, garden, and parking.
10 59 reviews
Bennington
10/05 – 10/07
HK$2888/nightTotal: HK$5776 (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.
9.6 127 reviews
Bennington
07/01 – 07/08
HK$1065/nightTotal: HK$7455 (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 90 reviews
Bennington
10/05 – 10/07
HK$1657/nightTotal: HK$3314 (2 )
Guest Cottage - Mountain Views, History & Hiking
1 2
house , Bennington
This renovated cottage is situated in Old Bennington, a short walk from the Bennington Monument, First Church, Robert Frost's grave, and the Bennington Museum, offering a peaceful and historic setting. The property has received excellent ratings for user experience, location, and cleanliness. The cottage is a private and secluded dwelling with its own entrance, accommodating up to two guests. Amenities include a fully equipped kitchen, air conditioning, a garden, a fitness centre, parking, and internet access, along with sustainable practices and charming design features.
10 82 reviews
Bennington
07/01 – 07/08
HK$2821/nightTotal: HK$19747 (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.
10 131 reviews
Bennington
07/01 – 07/08
HK$3106/nightTotal: HK$21742 (7 )
White Rock Farm
1 1
gîte , Bennington
This family-friendly farmhouse is situated just 4.7km from Bennington Potters Yard and within 10km of several other attractions including Fiddlehead at Four Corners, Howard Park, Robert Frost Stone House Museum, and the Bennington Museum. The property has received excellent ratings for its location, cleanliness, and overall user experience. This spacious farmhouse spans 223 square metres, comfortably accommodating up to 12 guests across five bedrooms and three bathrooms. Guests can enjoy a range of amenities including air conditioning, a terrace, a garden, and parking, as well as a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher.
8.5 27 reviews
Bennington
07/01 – 07/08
HK$1170/nightTotal: HK$8190 (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.
Bennington
07/01 – 07/08
HK$1640/nightTotal: HK$11480 (7 )
Bennington Gem W/ Smart Tv Near Historic District!
1 1
, Bennington
This Bennington cottage offers contactless check-in and is within walking distance of Bennington's town centre, close to the Bennington Arts Guild Gallery and Hemmings Motor News. The self-catering property sleeps two, includes a kitchen with fridge, microwave, and dishwasher, one bathroom, free on-site parking, and Wi-Fi; guests can easily explore Harmon Hill from this convenient location.
9.7 6 reviews
Bennington
07/01 – 07/08
HK$1694/nightTotal: HK$11858 (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.
Best family friendly Bennington holiday rentals
Among the 37 accommodations in Bennington, here are the 4 best family friendly rentals
9.6 201 reviews
Bennington
07/01 – 07/08
HK$1534/nightTotal: HK$10738 (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.
9.7 81 reviews
Bennington
07/01 – 07/08
HK$978/nightTotal: HK$6846 (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.
9.8 7 reviews
Bennington
10/05 – 10/07
HK$1290/nightTotal: HK$2580 (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.
10 9 reviews
Bennington
10/05 – 10/07
HK$2829/nightTotal: HK$5658 (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.
Best pet friendly Bennington holiday rentals
Among the 37 accommodations in Bennington, here are the 4 best pet friendly rentals
9.8 60 reviews
Bennington
07/01 – 07/08
HK$1179/nightTotal: HK$8253 (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.
10 3 reviews
Bennington
06/27 – 06/29
HK$2747/nightTotal: HK$5494 (2 )
Modern, Stylish Apartment On Stunning Horse Farm In Shaftsbury Vermont.
1 2
apartment , Shaftsbury
This Shaftsbury apartment, ideally situated near Harmon Hill and Prospect Mountain Cross-Country Ski Centre, offers convenient access to both outdoor pursuits and local shopping at Bennington Potters Yard and Fiddlehead at Four Corners. The one-bedroom flat sleeps four guests, boasting a queen-size bed, a luxurious shower, a living room with a futon, and a private outdoor sitting area, plus shared access to gazebos, gardens, and a pond.
Bennington
06/27 – 06/29
HK$5706/nightTotal: HK$11412 (2 )
New Log Cabin - Privacy, Views, Trails
1 2
cabin , Searsburg
This secluded mountain lodge in Searsburg, Vermont, offers breathtaking views and is situated 3 kilometres from the towns of Bennington and Wilmington, with close proximity to Woodford State Park and Molly Stark State Park. This rustic yet modern lodge accommodates 16 guests, featuring 2 bathrooms, a cosy fireplace with large windows, a spacious deck, and direct access to snowmobile trails, with nearby Nordic ski trails at Woodford State Park and opportunities for hiking, fishing, and swimming, as well as convenient access to Stratton and Mount Snow ski resorts.
9.7 49 reviews
Bennington
10/05 – 10/07
HK$2245/nightTotal: HK$4490 (2 )
Walkable Modern 2br In Downtown - Left Unit
2 2
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.
Frequently asked questions about holiday rentals in Bennington
What essentials should you bring along for a trip to Bennington, Vermont?
Pack for all types of weather, as Vermont's climate can be unpredictable. Comfortable walking shoes are a must for exploring the town and surrounding areas. Layers of clothing are essential, as temperatures can fluctuate significantly, especially during shoulder seasons. Don't forget sunscreen, insect repellent, and a rain jacket.
What are the best Airbnb and vacation rentals in Bennington?
What famous events or festivals are happening in Bennington, Vermont?
Bennington hosts several events throughout the year. The Bennington Battle Day Parade is a significant annual event commemorating a pivotal Revolutionary War battle. Check local listings for smaller, community-based events and festivals that might coincide with your visit.
What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Bennington, Vermont?
A daily budget of £150-£300 per person should cover accommodation, meals, local transport, and entry fees to attractions. This is a broad estimate, and costs can vary depending on your choices of accommodation, dining, and activities.
What are the best vacation rentals with a pool in Bennington?
Where can you find the best restaurants serving local dishes in Bennington, Vermont, and what are the must-try specialties?
The Walloomsac Inn is a popular choice, known for its refined New England cuisine. For a more casual setting, try the Four Chimneys Inn, which offers hearty, traditional dishes. Maple syrup, cheddar cheese, and locally sourced produce are regional staples you should definitely sample.
What are the best rentals for families and kids in Bennington?
What are some less-famous attractions in Bennington, Vermont that are worth a visit?
The Grandma Moses House and Studio is a fascinating look into the life of the renowned folk artist. The Monument and its grounds provide a tranquil escape, and exploring the nearby trails offers a chance to connect with nature. Many smaller galleries and craft shops in the town centre are worth browsing.
What are the best rentals or Airbnbs with a jacuzzi in Bennington?
What are the best activities for engaging with locals and understanding their culture in Bennington, Vermont?
Visiting local farmers' markets is a great way to meet residents and sample local produce. Attending community events or festivals provides opportunities for interaction. Striking up conversations with staff at local businesses can also offer insights into the local culture.
What unique natural landscapes and terrain features can travellers explore in and around Bennington, Vermont?
The Green Mountains offer a variety of landscapes, from rolling hills to steeper, more challenging terrain. Hiking trails abound, providing opportunities to explore forests, streams, and scenic overlooks. Mount Equinox offers panoramic views and various hiking trails to suit different fitness levels.
How many days are ideal for a trip to Bennington, Vermont, and what are some itinerary suggestions?
Two to three days allow for a good exploration of Bennington and its surroundings. A possible itinerary could include a day exploring the town's historical sites, a day hiking in the Green Mountains, and a day dedicated to relaxing and enjoying local cuisine. Adjust this based on your interests and available time.
Nearby regions
Best Bennington holiday rentals with a pool
Among the 37 accommodations in Bennington, here are the 1 best rentals with a pool
9.4 7 reviews
Bennington
07/01 – 07/08
HK$1332/nightTotal: HK$9324 (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 holiday rentals with parking
10 1 review
Bennington
07/01 – 07/08
HK$1696/nightTotal: HK$11872 (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.
9.7 27 reviews
Bennington
10/05 – 10/07
HK$2553/nightTotal: HK$5106 (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.
10 56 reviews
Bennington
10/05 – 10/07
HK$2798/nightTotal: HK$5596 (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.
9.6 5 reviews
Bennington
07/01 – 07/08
HK$1135/nightTotal: HK$7945 (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.