Bennington holiday rentals: compare the best deals
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.
10 78 reviews
Bennington
10/05 – 10/07
HK$2817/nighttotal: HK$5634 (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.
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.
Bennington
07/01 – 07/08
HK$1641/nighttotal: HK$11487 (7 )
Bennington Gem W/ Smart Tv Near Historic District!
1 2
, 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.
9.9 97 reviews
Bennington
07/01 – 07/08
HK$1243/nighttotal: HK$8701 (7 )
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.
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.
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.
9.6 201 reviews
Bennington
07/01 – 07/08
HK$1809/nighttotal: HK$12663 (7 )
1920's Bennington Vermont Guest Barn
1 2
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.
9.0 2 reviews
Bennington
06/27 – 06/29
HK$8716/nighttotal: HK$17432 (2 )
Charming Restored Log Cabin In Hoosick Falls Ny On The Vermont Border
4 2
farm , Hoosick Falls
This four-bedroom Vermont farmhouse, near Bennington, offers a family-friendly escape, situated approximately 5km from the Green Mountain National Forest and 10km from Bennington Battlefield Park. Sleeping up to ten guests, this self-catering property boasts a fully equipped kitchen with dishwasher and microwave, air conditioning, a terrace, garden, parking, and Wi-Fi; barbecue facilities are also available for outdoor dining.
9.4 10 reviews
Bennington
06/27 – 07/04
HK$7474/nighttotal: HK$52318 (7 )
Serene Getaway In The Vermont National Forrest
4 2
apartment , Woodford
This four-bedroom apartment is located near Williamstown, Vermont, just a short distance from the Appalachian Trail, MASS MOCA, the Clark Art Museum, the Williamstown Summer Theater, and a world-class Nordic centre. The apartment has received excellent user and location ratings, and a very good cleanliness rating. The property is a spacious home with two bathrooms, suitable for up to eight guests. The apartment comes with a fully equipped kitchen, a Jacuzzi, a garden, a sauna, parking, and internet access, making it ideal for families or groups seeking a relaxing and comfortable stay.
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.
9.9 111 reviews
Bennington
10/05 – 10/07
HK$1603/nighttotal: HK$3206 (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.
Best family friendly Bennington holiday rentals
Among the 37 accommodations in Bennington, here are the 4 best family friendly rentals
10 131 reviews
Bennington
07/01 – 07/08
HK$3422/nighttotal: HK$23954 (7 )
White Rock Farm
1 2
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.
10 82 reviews
Bennington
07/01 – 07/08
HK$3195/nighttotal: HK$22365 (7 )
Dreamy & Stylish Log Cabin Near Town W/ Fast Wifi
1 2
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 61 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.
9.7 49 reviews
Bennington
07/01 – 07/08
HK$1280/nighttotal: HK$8960 (7 )
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.
Best pet friendly Bennington holiday rentals
Among the 37 accommodations in Bennington, here are the 4 best pet friendly rentals
9.7 62 reviews
Bennington
10/05 – 10/07
HK$2245/nighttotal: HK$4490 (2 )
Walkable Modern 2br In Downtown - Right Unit
1 2
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.
9.7 6 reviews
Bennington
07/01 – 07/08
HK$1917/nighttotal: HK$13419 (7 )
Large Country Ranch On 2 Acres
4 2
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.
10 44 reviews
Bennington
06/27 – 07/04
HK$1074/nighttotal: HK$7518 (7 )
The Deer Crib
1 2
cabin , Hoosick Falls
This unique converted corn crib, near Hoosick Falls, New York, offers a tranquil off-grid escape on 230 acres of private land with access to local hiking trails. The one-bedroom dwelling sleeps two guests and features a gas cooktop, wood stove, seasonal outdoor shower, and an outhouse; activities include hiking, snowshoeing, cross-country skiing and horseback riding on the property.
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.
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
9.9 35 reviews
Bennington
07/01 – 07/08
HK$2750/nighttotal: HK$19250 (7 )
Vermont🍁🌲
3 2
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.
Best Bennington holiday rentals with parking
10 63 reviews
Bennington
06/27 – 07/04
HK$1624/nighttotal: HK$11368 (7 )
3-bedroom Country Home With Mountain Views
3 2
apartment , Shaftsbury
This three-bedroom Shaftsbury apartment, ideal for families, enjoys a peaceful countryside setting near mountains perfect for hiking and skiing, with nearby lakes for boating and streams for fishing, all within easy reach of local golf courses, museums and shops. Sleeping six guests, this self-catering property boasts a fully equipped kitchen (fridge, microwave), air conditioning, a garden, parking, and excellent guest reviews; enjoy the tranquil atmosphere and scenic farm views.
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.
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.
9.6 5 reviews
Bennington
10/05 – 10/07
HK$1863/nighttotal: HK$3726 (2 )
Cozy Loft Steps From Vt Downtown
1 2
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.