Vacation Rentals in Bennington, VT

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

Best family friendly Bennington, VT holiday rentals

Among the 37 accommodations in Bennington, VT, here are the 4 best family friendly rentals

North Bennington, Vt Conveniently Located Unit. - Bennington, VT
9.7 82 reviews
Bennington, VT
01/07 – 08/07
A$184/nighttotal: A$1288 (7 )

North Bennington, Vt Conveniently Located Unit.

1 2
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.
Walkable Modern 2br In Downtown - Right Unit - Bennington, VT
9.7 62 reviews
Bennington, VT
05/10 – 07/10
A$408/nighttotal: A$816 (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.
3-bedroom Country  Home With Mountain Views - Bennington, VT
10 63 reviews
Bennington, VT
27/06 – 04/07
A$295/nighttotal: A$2065 (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.
Awesome 3 Bedroom Apartment Close To It All - Bennington, VT
10 61 reviews
Bennington, VT
05/10 – 07/10
A$524/nighttotal: A$1048 (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.

Best pet friendly Bennington, VT holiday rentals

Among the 37 accommodations in Bennington, VT, here are the 4 best pet friendly rentals

Vermont🍁🌲 - Bennington, VT
9.9 35 reviews
Bennington, VT
01/07 – 08/07
A$499/nighttotal: A$3493 (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.
Modern, Stylish Apartment On Stunning Horse Farm In Shaftsbury Vermont. - Bennington, VT
10 3 reviews
Bennington, VT
27/06 – 04/07
A$351/nighttotal: A$2457 (7 )

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.
New Log Cabin - Privacy, Views, Trails - Bennington, VT
Bennington, VT
27/06 – 04/07
A$772/nighttotal: A$5404 (7 )

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.
Large Country Ranch On 2 Acres - Bennington, VT
9.7 6 reviews
Bennington, VT
01/07 – 08/07
A$348/nighttotal: A$2436 (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.

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

Historic Downtown Apartment Near Skatepark - Bennington, VT
8.5 27 reviews
Bennington, VT
01/07 – 08/07
A$240/nighttotal: A$1680 (7 )

Historic Downtown Apartment Near Skatepark

4 2
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.

Best Bennington, VT holiday rentals with parking

The Old Pine House - Bennington, VT
10 56 reviews
Bennington, VT
05/10 – 07/10
A$508/nighttotal: A$1016 (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.
Charming 2-bedroom Apartment In Superb Bennington With Wifi - Bennington, VT
9.8 7 reviews
Bennington, VT
05/10 – 07/10
A$234/nighttotal: A$468 (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.
Green Mountain Getaway - Bennington, VT
9.7 27 reviews
Bennington, VT
05/10 – 07/10
A$463/nighttotal: A$926 (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.
Cozy Loft Steps From Vt Downtown - Bennington, VT
9.6 5 reviews
Bennington, VT
05/10 – 07/10
A$338/nighttotal: A$676 (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.
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