Vacation rentals in Bennington, VT

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Bennington, VT vacation rentals
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Best Vacation rentals and Airbnb offers in Bennington, VT

Best family friendly Bennington, VT vacation rentals

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

Memes High Mountain Lake House - Bennington, VT
9.8 100 reviews

Memes High Mountain Lake House

apartment, Woodford
Meme's Lake House is a mountaintop retreat located in a private community near Wilmington, Vermont, less than 30 minutes from Mount Snow and a short drive from Stratton. The property consistently receives excellent ratings for location, cleanliness, and overall experience.
This 3-bedroom, 2-bathroom vacation rental comfortably accommodates up to 9 guests in its 1700 square feet of space. The property offers a fully equipped kitchen, a cozy wood-burning stove, a terrace, a garden, and access to a variety of seasonal activities including snowmobiling, ice fishing, and kayaking.
Quiet Apartment Getaway - Bennington, VT
9.6 62 reviews

Quiet Apartment Getaway

apartment, Bennington
This Bennington apartment rental offers a convenient Southern Vermont base for exploring nearby New York and Massachusetts, with easy access to Bennington's town center—though precise distances to specific landmarks require further inquiry.
The two-bedroom, one-bathroom unit sleeps five, features a full kitchen with fridge, freezer, microwave, and dishwasher, includes parking, internet access, and boasts a unique birch forest wall for guests to personalize.
Walkable Modern 2br In Downtown - Right Unit - Bennington, VT
9.7 65 reviews

Walkable Modern 2br In Downtown - Right Unit

apartment, Bennington
This Bennington apartment is conveniently located in the heart of town, just a short walk from Walmart and Hannaford, with easy access to nearby ski areas, mountains, hiking trails, and lakes. The apartment has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travelers.
This comfortable rental features two bedrooms and one bathroom, comfortably accommodating up to six guests. The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, a shared garden, and parking, ensuring a pleasant and convenient stay.
Green Mtn Farm House. Convenient To Ski Resorts - Bennington, VT
9.8 55 reviews

Green Mtn Farm House. Convenient To Ski Resorts

apartment, Woodford
This renovated farmhouse sits just across the street from Prospect Ski area, a short drive from Mount Snow and Manchester, offering a peaceful escape in the Vermont countryside. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The entire home is available for guest use, comfortably accommodating up to 6 people. Amenities include a fully equipped kitchen, a private garden, a fitness center, parking, and access to a trout pond, while nearby hiking trails and winter sports activities provide ample opportunities for exploration and recreation.

Best pet friendly Bennington, VT vacation rentals

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

Green Mountain Getaway - Bennington, VT
9.9 60 reviews

Green Mountain Getaway

apartment, Bennington
The Green Mountain Getaway is a three-bedroom, one-bathroom house in Bennington, Vermont, offering easy access to attractions like the Bennington Battle Monument and Oldcastle Theatre Company.
This Bennington vacation rental sleeps six, features a fully equipped kitchen with a fridge, microwave, and dishwasher, in-unit laundry, air conditioning, and a garden with parking; high-speed internet is also available.
1769 Henry House/tavern / Near Manchester - Bennington, VT
10 78 reviews

1769 Henry House/tavern / Near Manchester

apartment, Bennington
The Henry House, a historic landmark built in 1769, sits on 25 acres of meadows and mountains near the Walloomsac River and the Burt Henry Covered Bridge in Bennington, Vermont. The property has received excellent ratings for location, cleanliness, and overall user experience.
This charming house offers five bathrooms and can accommodate up to 10 guests. The Henry House features a fully equipped kitchen, air conditioning, a garden, parking, and internet access, along with access to the entire house and surrounding outdoor space.
!Charming Cabin,  Great Views - Bennington, VT
9.5 190 reviews

!Charming Cabin, Great Views

cabin, Shaftsbury
This Shaftsbury cabin is located just 20-30 minutes from both Bennington and Manchester, offering a peaceful escape in the Vermont countryside. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The 1150-square-foot cabin comfortably accommodates up to 7 guests with 2 bedrooms and 1 bathroom. Enjoy a range of amenities including a full kitchen, a fire pit, a porch swing, a hammock, and access to hiking trails, a pond, and a working farm with chickens, ducks, and goats.
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 is located in a peaceful rural setting near Bennington, Vermont, just 2 miles from local breweries and a short walk from Bennington College. The property boasts excellent ratings for user experience, location, and cleanliness.
This charming home features 5 bedrooms and 3 bathrooms, accommodating up to 13 guests. Enjoy modern amenities like a new kitchen, gas fireplace, under-floor heating, updated bathrooms, and a large southern-facing window gallery, as well as scenic views, wildlife viewing, and access to a working hemp farm.

Frequently Asked Questions about vacation rentals in Bennington, VT

  • 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 hiking trails. Layers are key, as temperatures can fluctuate. Don't forget insect repellent, especially during warmer months.
  • What are the best Airbnb and vacation 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 vacation rentals in Bennington, VT among travelers.

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

    Bennington hosts the Bennington Battle Day Parade each August, commemorating a significant Revolutionary War battle. Check local listings for smaller, community events throughout the year. The town also participates in the broader Vermont fall foliage celebrations.
  • 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 $150-$300 per person is a reasonable estimate, depending on your lodging choices and dining preferences. This includes accommodation, meals, local transportation (car rental recommended for exploring the surrounding area), and entry fees for attractions. Budget-conscious travelers can certainly spend less.
  • What are the best vacation rentals with a pool in Bennington, VT?

    The best vacation 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 for upscale dining, while the Four Chimneys Inn offers a more casual atmosphere. Many local restaurants feature Vermont cheese and maple syrup in their dishes. Try the Vermont cheddar or a maple-glazed anything!
  • 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 the visit?

    The Bennington Center for the Arts offers a glimpse into the local art scene. Exploring the charming downtown area with its unique shops is also a rewarding experience. A drive along Vermont Route 9 offers scenic overlooks of the Green Mountains.
  • What are the best rentals or Airbnbs with a jacuzzi in Bennington, VT?

    Two Brooks Lodge and Historic Inn Wbar Room - Hot Tub - 6 Bedrooms are the best vacation rentals or Airbnb with a jacuzzi in Bennington, VT.

  • What are the best activities for engaging with locals and understanding their culture in Bennington, Vermont?

    Visiting local farmers' markets allows you to interact with residents and sample local produce. Attending community events or festivals offers opportunities to connect with locals. Striking up conversations at local restaurants and shops is a great way to learn more about Bennington's culture.
  • What unique natural landscapes and terrain features can travelers explore in and around Bennington, Vermont?

    The Green Mountains offer a variety of hiking trails, from easy walks to challenging climbs. The area is known for its forests, rolling hills, and scenic overlooks. Nearby Mount Equinox offers spectacular views from its summit.
  • How many days are ideal for visiting Bennington, Vermont, and what are some itinerary suggestions?

    Two to three days allows for a good exploration of Bennington and its surroundings. Day one could focus on the town itself, visiting the museum and historical sites. Day two could involve hiking or exploring the Green Mountains. A third day could be dedicated to exploring nearby towns or relaxing.

Nearby regions

Best Bennington, VT vacation rentals with a pool

Among the 48 accommodations in Bennington, VT, here are the 4 best rentals with a pool

A Cozy Home Nestled In The Green Mountains Of Vermont! - Bennington, VT
8.8 3 reviews

A Cozy Home Nestled In The Green Mountains Of Vermont!

apartment, Pownal
This Williamstown vacation rental is located in the peaceful countryside of Pownal, just a short drive from the town's museums and attractions. It's received excellent guest ratings, making it a popular choice for travelers.
The apartment has four bedrooms and two bathrooms, accommodating up to seven guests comfortably. Enjoy the amenities like a swimming pool, a terrace, and a garden, as well as activities like hiking, biking, and skiing in the surrounding area.
24 Acre Southern Vermont Luxury Hilltop Retreat - Private Pool & Panoramic Views - Bennington, VT
10 1 review

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

apartment, Stamford
This secluded hillside residence in Stamford, Vermont, sits on 24 private acres with Green Mountain views, located 7 minutes from Mass MoCA and 20 minutes from The Clark Art Institute.
This 4500 sq ft home accommodates up to 8 guests with 4 bedrooms, 3 bathrooms, a bonus sleeping room, a stone fireplace, a bar area, and a private in-ground swimming pool, with nearby access to hiking, skiing at Mount Snow (22 miles) and Stratton Mountain (38 miles), and golf.
Karin's Place: Unique And Grand Guest House W/pool - Bennington, VT
9.8 51 reviews

Karin's Place: Unique And Grand Guest House W/pool

apartment, Pownal
Karin's Place is a spacious 8,000 square-foot estate located in the woods of Bennington, Vermont, just four miles from the town of Bennington and nine miles from Williamstown, Massachusetts. It has received excellent ratings for location, cleanliness, and user experience.
This large home can accommodate up to 12 guests and features a unique design with two separate living spaces. Karin's Place offers a variety of amenities, including a private pool, hot tub, sauna, playground, farm animals, and access to cross-country ski trails.
Farm-to-table Eating, Good Hot Tub Soak, S'mores Around Fire Pit, Seasonal Pool! - Bennington, VT
9.4 88 reviews

Farm-to-table Eating, Good Hot Tub Soak, S'mores Around Fire Pit, Seasonal Pool!

apartment, Pownal
This Pownal apartment is a short drive from both Williamstown and Bennington, offering easy access to the attractions and amenities of these vibrant towns while still enjoying the peace and quiet of the Vermont countryside. The apartment has earned excellent user ratings for its comfort, amenities, and location.
The spacious 1,000 square foot apartment can accommodate up to six guests with a queen bedroom, a king-sized bed in a large alcove, and a comfortable double pull-out sofa. Enjoy amenities like a private deck, hot tub, and access to a seasonal pool, along with a fully equipped kitchen, laundry room, and a heated mudroom for storage.

Best Bennington, VT vacation rentals with parking

Walkable Modern 2br In Downtown - Left Unit - Bennington, VT
9.7 52 reviews

Walkable Modern 2br In Downtown - Left Unit

apartment, Bennington
This modern apartment is located in central Bennington, within walking distance of Walmart, Hannaford, and various retail stores, making it a convenient base for exploring the town. The apartment is part of a two-family home, offering a sense of privacy while still being close to other guests, with a capacity of 6 people. The apartment features a fully equipped kitchen, air conditioning, and free parking, and is pet-friendly, making it a comfortable and convenient option for families and groups.
< 1 Mi To Historic District! Retreat In Bennington - Bennington, VT
8.0 2 reviews

< 1 Mi To Historic District! Retreat In Bennington

cottage, Bennington
This Bennington vacation home offers convenient access to Green Mountain National Forest (a 5-minute walk), the Hemmings Motor News Car Lover's Convenience Store & Vehicle Display (a 5-minute walk), and Fiddlehead at Four Corners and Harmon Hill (within a 10-minute drive).
The fully equipped kitchen includes an oven, stovetop, microwave, and dishwasher; free Wi-Fi is available in public areas, and free on-site parking is provided.
Mountain Sanctuary Dome Rustic Solitude 5br - Bennington, VT
9.8 11 reviews

Mountain Sanctuary Dome Rustic Solitude 5br

apartment, Bennington
This Pownal vacation home, near Green Mountain National Forest and within six miles of Taconic Ridge State Forest and Southern Vermont College, offers easy access to outdoor recreation and cultural attractions like the Solomon Wright Public Library and Bennington Center for the Arts.
This five-bedroom, two-bathroom house sleeps twelve guests and features a fully equipped kitchen with a refrigerator and stovetop, free WiFi, a fireplace, a terrace, a garden, parking, and a washing machine; on-site amenities include barbecue grills.
Two Brooks Lodge - Bennington, VT
9.1 188 reviews

Two Brooks Lodge

house, Bennington
Two Brooks Lodge is located in a peaceful rural area near Bennington, Vermont, just a short drive from attractions like the Bennington Battle Monument and the Bennington Museum. The property has received very good ratings for cleanliness, user experience, and location.
This 3-bedroom home, with a total floor area of 1350 square feet, comfortably sleeps up to 8 guests. Enjoy modern amenities like free Wi-Fi, a fully equipped kitchen, and a private terrace with views of the river and surrounding mountains.
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