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

Enjoy Summer & Private, Peace And  Relaxation - Bennington, VT
9.8 42 reviews

Enjoy Summer & Private, Peace And Relaxation

apartment, Hoosick Falls
This secluded vacation rental is located on a private 5-acre lot on the border of New York and Vermont, within a 30-60 minute drive of several ski areas, offering a peaceful escape from the city. This charming home features two bathrooms and can accommodate up to five guests.
The property offers a variety of amenities, including a fully equipped kitchen, air conditioning, free parking, and high-speed internet. Enjoy the expansive deck, relax in the oversized soaking tub, or gather around the fire pit for a memorable evening.
Two Brooks Lodge - Bennington, VT
9.1 193 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.
Walkable Modern 2br In Downtown - Left Unit - Bennington, VT
9.8 57 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.
Green Mtn Farm House. Convenient To Ski Resorts - Bennington, VT
9.8 56 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

Breathtaking Mtn Views: Stylish Rustic Retreat! - Bennington, VT
10 31 reviews

Breathtaking Mtn Views: Stylish Rustic Retreat!

house, Pownal
This two-bedroom vacation home near Pownal, Vermont, offers easy access to the Bennington Battle Monument (7.4 miles away) and is conveniently located for exploring both Vermont and nearby New York State.
The 2,000-square-foot property features a fully equipped kitchen, two bathrooms, air conditioning, free Wi-Fi, and parking, comfortably accommodating families or small groups.
Vt Farmhouse Private, Peaceful And Beautiful - Bennington, VT
9.8 175 reviews

Vt Farmhouse Private, Peaceful And Beautiful

apartment, Shaftsbury
This family-friendly farm stay is located near Shaftsbury, Vermont, just 6 miles from Arlington Town Forest, New Skete Monastery, and the Shaftsbury Historical Society Museum. Guests consistently rate this property excellent for location, cleanliness, and overall experience.
This 2,250 square foot vacation rental comfortably accommodates up to 6 guests in its 2 bedrooms and 2 bathrooms. Amenities include a fully equipped kitchen, air conditioning, a private terrace, a garden, and parking, perfect for enjoying the peace and quiet of the surrounding countryside.
!Charming Cabin, Great Views - Bennington, VT
9.5 193 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.
Farm-to-table Eating, Good Hot Tub Soak, S'mores Around Fire Pit, Seasonal Pool! - Bennington, VT
9.2 91 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.

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

Vintage Barn Apt-pool-hottub-firepit-farms-foliage - Bennington, VT
9.4 374 reviews

Vintage Barn Apt-pool-hottub-firepit-farms-foliage

farm, Pownal
This renovated dairy barn is located in the tiny village of Pownal Center, Vermont, close to the borders of Massachusetts and New York, offering a peaceful retreat in a rural setting. The property consistently receives excellent ratings for its location, cleanliness, and overall guest experience.
This unique farmhouse features a 2,100 square foot layout with two bedrooms and one bathroom. Guests can enjoy a chef's kitchen, a spacious outdoor living area with a pool, hot tub, fire pit, and patio, a separate guest apartment, an electric car charging station, and ample parking.
A Cozy Home Nestled In The Green Mountains Of Vermont! - Bennington, VT
9.0 4 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
9.6 5 reviews

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.
Farm-to-table Eating, Good Hot Tub Soak, S'mores Around Fire Pit, Seasonal Pool! - Bennington, VT
9.2 91 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

Clover Hill Farm & Country Inn - Bennington, VT
9.6 1 review

Clover Hill Farm & Country Inn

farm, Williamstown
Farm rental with an excellent rating of 96% based on 1 reviews. You will stay in Williamstown.
Services and facilities include a garden, air conditioning and a terrace.
Studio Style Vintage Garden Bungalow - Bennington, VT
9.1 147 reviews

Studio Style Vintage Garden Bungalow

studio, Shaftsbury
This Shaftsbury Vermont studio guest house is located on a 22-acre farm near Lake Paran, the Arlington Covered Bridge, and several marble quarries, all within walking distance or a short drive.
The renovated unit, sleeping two, offers a kitchenette with microwave and refrigerator, a private bathroom, and access to on-site amenities including a gas grill, bikes (summer), farm-fresh eggs, and a shared barn available for rent for events.
Charming 3-bedroom Lakefront Cottage In Woodford Vt With Wifi Access - Bennington, VT
8.0 7 reviews

Charming 3-bedroom Lakefront Cottage In Woodford Vt With Wifi Access

cottage, Woodford
This three-bedroom Woodford cottage, near Bennington, Vermont, offers waterfront access and proximity to the Robert Frost Stone House Museum and Bennington Museum.
The 3-bedroom, 1-bathroom house sleeps five, features a microwave, WiFi, and parking, and is close to winter sports and shopping at Fiddlehead at Four Corners and Bennington Potters Yard.
< 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 Bennington vacation rental is conveniently located within walking distance of Hemmings Motor News and a short drive from Bennington Potters Yard. The area offers a mix of historical sites, local shops, and restaurants, making it a great base for exploring Bennington.
This one-bedroom apartment offers 1,000 square feet of space and can comfortably accommodate up to four guests. Amenities include a fully equipped kitchen, parking, internet access, and a washer and dryer, ensuring a comfortable and convenient stay.
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