Vacation Rentals in Bennington, VT

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Bennington, VT holiday rentals
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48 Holiday rentals and Airbnb in Bennington, VT

Best family friendly Bennington, VT holiday rentals

Among the 48 accommodations in Bennington, VT, here are the 4 best family friendly rentals

"The Chambers" - Bennington, VT
9.8 110 reviews

"The Chambers"

apartment, Pownal
This charming apartment is located in Pownal, Vermont, just a short distance from Williamstown, Massachusetts, home to Williams College, the Williamstown Theatre Festival, and the Clark Art Museum. The apartment enjoys excellent ratings for location, cleanliness, and overall user experience.
This second-floor flat offers a private entrance and features a unique curved staircase. Guests can enjoy a fully equipped kitchen, Wi-Fi, satellite TV, outdoor seating, a chiminea, and a BBQ area.
Mountains, Pond, Old Barn, Hiking Trails- Quintessential Vermont - Bennington, VT
9.5 191 reviews

Mountains, Pond, Old Barn, Hiking Trails- Quintessential Vermont

cabin, Shaftsbury
This charming cabin is situated in Shaftsbury, Vermont, just 20-30 kilometres from Bennington and Manchester, offering a peaceful retreat in a rural setting. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The property spans 107 square metres and comfortably accommodates up to seven guests in its two bedrooms and one bathroom. Enjoy the modern conveniences, farm animal encounters, and outdoor activities, including hiking trails, a pond, and a fire pit.
1920's Bennington Vermont Guest Barn - Bennington, VT
9.6 207 reviews

1920's Bennington Vermont Guest Barn

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.
Suite Sunset
311 Rice Lane
Bennington Vt - Bennington, VT
9.9 112 reviews

Suite Sunset 311 Rice Lane Bennington Vt

apartment, Bennington
This Bennington apartment is situated on a private 50-acre property, less than 1.6 kilometres from Bennington College and close to the town centre.
The self-contained apartment offers a private entrance, spacious living areas, and a fully equipped kitchen, comfortably accommodating up to three guests.

Best pet friendly Bennington, VT holiday rentals

Among the 48 accommodations in Bennington, VT, here are the 4 best pet friendly rentals

Meme's High Mountain Lake House - Bennington, VT
9.8 101 reviews

Meme's High Mountain Lake House

apartment, Woodford
Meme's lake house is a mountaintop retreat in Vermont, located just 48 kilometres from Mount Snow and 24 kilometres from the town of Wilmington. The property has consistently received excellent user ratings for its location, cleanliness, and overall experience.
This spacious three-bedroom, two-bathroom holiday home can accommodate up to nine guests and spans 158 square metres. It offers a range of amenities, including a fully equipped kitchen, a terrace, a garden, and a private lakefront with a sandy beach and a screened-in gazebo.
Guest Cottage - Mountain Views, History & Hiking - Bennington, VT
10 94 reviews

Guest Cottage - Mountain Views, History & Hiking

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.
Private 1800s Family Farmhouse, Lush Rolling Hills - Bennington, VT
9.9 59 reviews

Private 1800s Family Farmhouse, Lush Rolling Hills

gîte, Bennington
This renovated farmhouse, located just two miles from three local breweries and a 45-minute walk from Bennington College, offers a tranquil escape in a rural setting near Bennington, Vermont. With excellent user, location, and cleanliness ratings, this property provides a comfortable and enjoyable stay for visitors.
The farmhouse, suitable for up to 13 guests, features five bedrooms and three bathrooms, making it ideal for families or groups. Enjoy modern amenities such as a fully equipped kitchen, under-floor heating, high-speed Wi-Fi, and a gas fireplace, while also experiencing the charm of a historic property with stunning views of Mt. Anthony and opportunities for wildlife viewing.
Large Country Ranch On 2 Acres - Bennington, VT
9.7 6 reviews

Large Country Ranch On 2 Acres

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.

Frequently asked questions about holiday rentals in Bennington, VT

  • What essentials should you bring along for a trip to Bennington, Vermont?

    Pack for all types of weather, as Vermont experiences distinct seasons. Comfortable walking shoes are a must for exploring the town and its trails. Layers of clothing are recommended, including a waterproof jacket and warm sweater, even in summer. Don't forget insect repellent, especially during warmer months.
  • What are the best Airbnb and holiday rentals in Bennington, VT?

    Cozy Modern Sugar House With Spectacular Views, Victorian Home In Bennington - Vermont and Scenic Vermont Studio are the most popular Airbnb and holiday rentals in Bennington, VT among travellers.

  • What famous events or festivals are happening in Bennington, Vermont?

    Bennington hosts several local events throughout the year. The Bennington Battle Day Parade is a significant annual event commemorating the battle. Many smaller, local festivals and craft fairs occur throughout the summer and autumn, celebrating local produce and artistry. Check local listings for specific dates.
  • What are the most popular Airbnbs in Bennington, VT?

    Among the Airbnbs in Bennington, VT, Cozy Modern Sugar House With Spectacular Views, Scenic Vermont Studio and Cooper's Place are the most popular ones.

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Bennington, Vermont?

    A daily budget of approximately £150-£300 per person should comfortably cover accommodation, meals, local transportation (consider car rental for exploring the surrounding areas), and entry fees for attractions. This is just an estimate, and costs can vary depending on your choices.
  • What are the best holiday rentals with a pool in Bennington, VT?

    The best holiday rental with a pool in Bennington, VT is Historic Home In Old Bennington - Vermont.

  • 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 dining experience, try the Four Corners Restaurant, which offers classic American fare with a Vermont twist. Be sure to sample local cheeses, maple syrup products, and hearty stews – quintessential Vermont flavours.
  • What are the best rentals for families and kids in Bennington, VT?

    The best rentals for families and kids in Bennington, VT are Suite Sunset 311 Rice Lane Bennington Vt, Two Brooks Lodge and Awesome 3 Bedroom Apartment Close To It All.

  • What are some less-famous attractions in Bennington, Vermont that are worth a visit?

    The Bennington Museum, while not entirely unknown, often gets overlooked. It houses a significant collection of Vermont art and history. Exploring the town's charming streets and discovering local shops and galleries can also be a rewarding experience. Consider a hike on a less-traveled trail in the nearby Green Mountains.
  • What are the best rentals or Airbnbs with a jacuzzi in Bennington, VT?

    The best holiday rentals or Airbnb with a jacuzzi in Bennington, VT are Two Brooks Lodge, Perfect For Leaf Peeping W\/bar Room - Hot Tub and Historic Inn Wbar Room - Hot Tub - 6 Bedrooms.

  • 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 interact with residents and learn about local produce and traditions. Attending a local event or festival allows for immersion in the community spirit. Striking up conversations with staff at local businesses can also lead to interesting insights into the local culture.
  • What unique natural landscapes and terrain features can travellers explore in Bennington, Vermont?

    Bennington's location in the Green Mountains offers opportunities for hiking, with trails ranging in difficulty. The area features rolling hills, forests, and scenic overlooks. Exploring the Mount Anthony State Park provides access to stunning views and hiking opportunities.
  • How many days are ideal for a visit to Bennington, Vermont, and what are some itinerary suggestions?

    Two to three days provide enough time to explore Bennington's key attractions and enjoy some of the surrounding natural beauty. A possible itinerary could include a day exploring the town's historical sites, a day hiking in the Green Mountains, and a day relaxing and enjoying local cuisine.

Nearby regions

Best Bennington, VT holiday rentals with a pool

Among the 48 accommodations in Bennington, VT, here are the 1 best rentals with a pool

24 Acre Southern Vermont Luxury Hilltop Retreat - Private Pool & Panoramic Views - Bennington, VT
9.0 2 reviews

24 Acre Southern Vermont Luxury Hilltop Retreat - Private Pool & Panoramic Views

apartment, Stamford
This expansive four-bedroom residence in Stamford offers a secluded hillside setting on 9.7 hectares with Green Mountain views, located 7 minutes from Mass MoCA and 32 kilometres from The Clark Art Institute and towns such as Wilmington and Williamstown.
This 418 square metre holiday home accommodates up to eight guests and features a swimming pool, terrace, fireplace, and bar area, providing an ideal base for outdoor pursuits including hiking, skiing at Mount Snow (35 kilometres) and Stratton (61 kilometres), and golf at Stamford Valley Golf Course.

Best Bennington, VT holiday rentals with parking

< 1 Mi To Historic District! Retreat In Bennington - Bennington, VT
10 1 review

< 1 Mi To Historic District! Retreat In Bennington

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.
Charming 3-bedroom Vermont House With Outdoor Sauna And Mountain Views - Bennington, VT
9.6 5 reviews

Charming 3-bedroom Vermont House With Outdoor Sauna And Mountain Views

apartment, Stamford
This renovated three-bedroom flat in Stamford offers an excellent user rating and is situated 48 kilometres from the ski slopes, with the North Adams Public Library and East Hoosac Quaker Meetinghouse within easy reach.
This accommodation, suitable for up to seven guests, features a sauna, internet, kitchen, and parking, and is conveniently located near North Adams Centre and North Adams Gateway Centre for shopping, as well as Hopkins Observatory and the 62 Centre for Theatre and Dance.
"Daylight Shaftsbury Apartment" - Bennington, VT
10 6 reviews

"Daylight Shaftsbury Apartment"

apartment, Shaftsbury
This Shaftsbury dwelling offers a private, 100-square-meter open-concept living space on the lower level of a Vermont home, boasting breathtaking views overlooking Furnace Brook and East Mountain.
Guests can enjoy exclusive access to a private garden, fire pit, and hot tub, with opportunities for wildlife viewing, accommodating up to three people with one bedroom and one bathroom.
The Shepherd's Retreat - Bennington, VT
9.9 206 reviews

The Shepherd's Retreat

apartment, Pownal
This self-contained ground-floor apartment in Pownal, Vermont, is minutes from Bennington and a short drive (approximately 30-45 minutes depending on traffic and exact location within the Berkshires) from MASS MoCA.
The one-bedroom flat features an open-plan kitchen and living area, sleeping up to six guests with a queen bed, air mattresses, and a sofa bed, and includes a private patio with BBQ, on-site laundry facilities (small charge for supplies), and free parking.
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