Holiday Rentals in Bennington, VT

37 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Bennington, VT holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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
112 €/nighttotal: 784 € (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.
Vermont Downtown Oasis - Two Bedroom In Picturesque Downtown - Bennington, VT
10 10 reviews
Bennington, VT
05/10 – 07/10
312 €/nighttotal: 624 € (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.
1920's Bennington Vermont Guest Barn - Bennington, VT
9.6 204 reviews
Bennington, VT
01/07 – 08/07
200 €/nighttotal: 1400 € (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.
Charming 2-bedroom Apartment In Superb Bennington With Wifi - Bennington, VT
9.8 7 reviews
Bennington, VT
05/10 – 07/10
142 €/nighttotal: 284 € (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.

Best pet friendly Bennington, VT holiday rentals

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

Walkable Modern 2br In Downtown - Right Unit - Bennington, VT
9.7 62 reviews
Bennington, VT
01/07 – 08/07
130 €/nighttotal: 910 € (7 )

Walkable Modern 2br In Downtown - Right Unit

2 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.
Private Home On 37 Acres With Stunning Mountain Views - Bennington, VT
9.3 33 reviews
Bennington, VT
27/06 – 29/06
1577 €/nighttotal: 3154 € (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.
The Deer Crib - Bennington, VT
10 44 reviews
Bennington, VT
27/06 – 04/07
118 €/nighttotal: 826 € (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.
Green Mountain Getaway - Bennington, VT
9.9 55 reviews
Bennington, VT
05/10 – 07/10
234 €/nighttotal: 468 € (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.

Frequently asked questions about holiday rentals in Bennington, VT

  • What are the must-see sights in Bennington, Vermont?

    Bennington boasts several must-see attractions. The Old First Church, a beautiful example of New England architecture, is a popular spot. The Bennington Battle Monument, a towering structure commemorating a pivotal Revolutionary War battle, offers stunning views. The Robert Hull Fleming Museum at the University of Vermont's Bennington campus showcases diverse art and exhibits. For history buffs, the Bennington Museum is a great choice, detailing the area's rich past.
  • 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.

  • Are there any unique natural phenomena in Bennington, Vermont?

    While Bennington doesn't have dramatic, unique natural phenomena like geysers, its landscape itself is quite distinctive. The Green Mountains provide breathtaking scenery, offering hiking trails with varied difficulty levels and panoramic views. The area's numerous forests and rivers also provide opportunities for nature lovers to enjoy the peaceful surroundings. Specific locations like Mount Anthony State Park offer great hiking and scenic overlooks.
  • 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 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, including a waterproof jacket and warm sweater, even during summer. Don't forget sunscreen, insect repellent, and a hat for sun protection. A reusable water bottle is also highly recommended.
  • 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.

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

    Bennington hosts several events throughout the year. The Bennington Battle Day Parade, a significant historical commemoration, is a notable annual event. Local farmers' markets offer a taste of regional produce and crafts. Check local listings for smaller, community-based events that may be happening during your visit.
  • What are the best rentals for families and kids in Bennington, VT?

    The best rentals for families and kids in Bennington, VT are Two Brooks Lodge, Suite Sunset 311 Rice Lane Bennington Vt and Perfect For Leaf Peeping W\/bar Room - Hot Tub.

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

    A daily budget will vary greatly depending on your travel style. Accommodation costs can range from £50 to £200 per night, food can range from £25 to £75 per day, and activities and transportation can add another £20 to £50 per day. Therefore, a reasonable daily budget could range from £100 to £300 per person, depending on your choices.
  • What are the best rentals or Airbnbs with a jacuzzi in Bennington, VT?

  • Where can you find the best restaurants serving local dishes in Bennington, Vermont, and what are the must-try specialties?

    Bennington has several charming restaurants. The Walloomsac Inn is a well-regarded option, known for its upscale dining experience. For more casual fare, there are various cafes and pubs around town. Local specialties often feature Vermont cheese, maple syrup, and seasonal produce. Look for dishes incorporating these ingredients for an authentic taste of the region.
  • What are some less-famous attractions in Bennington, Vermont that are worth a visit?

    Beyond the main attractions, explore the charming streets of downtown Bennington. Discover hidden gems like local art galleries and independent shops. The Bennington College campus is architecturally interesting and worth a stroll. Consider visiting some of the smaller, local museums or historical societies in the area.
  • 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 community events or local festivals allows for engaging with the community. Striking up conversations with staff at local businesses or restaurants is another easy way to learn about daily life in Bennington.
  • What unique natural landscapes and terrain features can travellers explore in Bennington, Vermont?

    Bennington's landscape is characterised by the Green Mountains, offering hiking trails and scenic overlooks. The area's forests and rivers provide opportunities for outdoor activities such as hiking, fishing, and kayaking. Mount Anthony State Park is a great starting point for exploring the natural beauty of the area.
  • How many days are ideal for a visit to Bennington, Vermont, and what are some itinerary suggestions?

    Two to three days is a good amount of time to experience Bennington's highlights. Day one could focus on historical sites like the Bennington Battle Monument and the Bennington Museum. Day two could involve exploring the natural surroundings, perhaps with a hike in Mount Anthony State Park. A third day could be dedicated to exploring the town, visiting local shops and restaurants.

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

Dreamy & Stylish Log Cabin Near Town W/ Fast Wifi - Bennington, VT
10 82 reviews
Bennington, VT
01/07 – 08/07
311 €/nighttotal: 2177 € (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.

Best Bennington, VT holiday rentals with parking

The Old Pine House - Bennington, VT
10 56 reviews
Bennington, VT
05/10 – 07/10
309 €/nighttotal: 618 € (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.
Awesome 3 Bedroom Apartment Close To It All - Bennington, VT
10 61 reviews
Bennington, VT
05/10 – 07/10
319 €/nighttotal: 638 € (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.
Cozy Loft Steps From Vt Downtown - Bennington, VT
9.6 5 reviews
Bennington, VT
01/07 – 08/07
131 €/nighttotal: 917 € (7 )

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.
< 1 Mi To Historic District! Retreat In Bennington - Bennington, VT
10 1 review
Bennington, VT
01/07 – 08/07
183 €/nighttotal: 1281 € (7 )

< 1 Mi To Historic District! Retreat In Bennington

1 2
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.
©2026 cozycozy.com