Bennington holiday homes

We found 1,621 holiday rentals — enter your dates for availability

Discover a selection of 17 homes and other holiday rentals in Bennington that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the amenities that you expect and more, which might include Wi-Fi and a hot tub. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Bennington

Showing deals for:18 Jul - 25 Jul

Image gallery for The Shred Chalet, Walk to Lifts and Ski-in!

Private kitchen
10 out of 10 rating
Exceptional
(5 reviews)

The Shred Chalet, Walk to Lifts and Ski-in!

West Dover, VT

8% off
Price is NZ$11,377
NZ$1,625 per night
includes taxes & fees
The Shred Chalet, Walk to Lifts and Ski-in!

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Adventurous Bennington will entice you

Enjoy the museums and other features of Bennington. This city's skiing, mountain views and hiking draw many visitors. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Bennington

Do you want to find top things to see and do during your stay? Travellers enjoy Bennington for its skiing, hiking and golfing. Venture out of your cosy holiday rental and experience everything that makes Bennington a fun spot to go on holiday. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Prospect Mountain Cross-Country Ski Center (7.2 mi / 11.6 km)
  • Sugar Shack (14.4 mi / 23.1 km)
  • Waubeeka Golf Links (15.7 mi / 25.3 km)
  • Mount Snow (15.7 mi / 25.3 km)
  • The Hermitage Club (15.9 mi / 25.5 km)
  • The Hermitage Golf Club (16.5 mi / 26.6 km)

Exploring the mountains and other natural features in Bennington

Whether you're looking for adventure or just want to take in the scenery, Bennington is a great spot to appreciate mother nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Shaftsbury State Park (9.6 mi / 15.4 km)
  • Grafton Lakes State Park (14.1 mi / 22.7 km)
  • Taconic Lake (14.4 mi / 23.1 km)
  • Windsor Lake Park (15 mi / 24.1 km)
  • Lake Lauderdale (16.4 mi / 26.4 km)
  • Harriman Reservoir (16.5 mi / 26.5 km)

Seasonal weather averages in Bennington

Bennington is well known for its skiing. If you've planned your trip around snowy activities, consider visiting in January, March, February or December, when snowfall averages 21 cm and temperatures average -3°C.

Travelling to and around Bennington

Fly into Albany, NY (ALB-Albany Intl.), the closest airport, located 31.7 mi (51 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 31.9 mi (51.4 km) away.

Frequently asked questions

What is the best area to stay in Bennington when booking a holiday home?
Old Bennington is among the more sought-after neighbourhoods to book a holiday home in Bennington. Spend your getaway here and enjoy the privacy and convenience that comes with having a place all to yourselves.
What is the most popular type of holiday home accommodation in Bennington?
The most sought-after types of holiday homes in Bennington are houses. Ready for more choices? Bookabach has plenty of options to match the diverse needs of our guests, so you’ll see holiday properties in all sizes and shapes. The perfect home away from home is waiting for you — get yours today.
How much does it cost to rent a holiday home in Bennington?
Different factors can influence how much you pay for a holiday home in Bennington, such as the type of property, season and length of stay. But, all our holiday homes have one thing in common — unbeatable value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Bennington?
The average price for a holiday home near the beach in Bennington depends on when you’re going and the style and size of property you’re searching for. Find prices easily on Bookabach by entering your travel dates. Then make use of the filter tool to select the number of bedrooms and amenities essential to you, like a pool, WiFi and air conditioning.
Are there pet-friendly holiday homes in Bennington?
Yes. There are. You’ll have a choice of 418 holiday homes that allow pets in Bennington. Several of our pet-friendly holiday homes even come with space outdoors for your four-legged friend to have fun in, special dog beds, complimentary treats and proximity to parks and green space. Apply the “Pets allowed” filter to find your pawfect digs on Bookabach.
Can I rent a house with a pool in Bennington?
Add a whole new level of fun to your getaway by booking your crew into one of the 130 houses with a private pool in Bennington. Use our handy search filter to find the kind of property you want on Bookabach, and then spend carefree days playing and splashing in a swimming pool that’s for your use only.
What are popular home amenities in Bennington?
The most popular home amenities people are searching for in Bennington include ski-in/ski-out facilities, a chef and a sauna. Whether you’re on a trip with your besties, family or even pets, Bookabach holiday homes provide the best amenities for starting a new adventure with your loved ones.
Are there large group holiday homes in Bennington?
With 158 properties that can host 10 guests or more in Bennington, there’s no need to cross anyone off the invite list. From fun family get-togethers to special events like Christmas and birthday parties, Bookabach will help you find a large group home to match the occasion.
Are there holiday homes in Bennington that welcome kids?
Bennington has 417 family-friendly holiday homes to choose from. And finding a stay that welcomes kiddos is easy with our “Properties good for families” filter. On top of having the whole place to yourselves, you’ll also get perks and amenities like bunk beds, yards and private pools.
What are the top attractions for families in Bennington?
Keep the kids occupied at these fabulous family-friendly attractions in Bennington:

  • Woodford State Park
  • Bennington Centre for the Arts
  • Norman Rockwell Exhibition

Are there one-bedroom holiday homes in Bennington?
Bennington has 44 one-bedroom homes available. Often situated in prime areas due to their compact size, a one-bedroom property is ideal if you’re getting away with your partner or a pal. And with plenty of home comforts like air conditioning and more privacy than a standard hotel, you’ll be able to relax while enjoying this top destination.
Can I find two-bedroom holiday homes in Bennington?
Bennington has 40 two-bedroom holiday homes to select from. Go for a holiday home with all the privacy and comfort you need at a fantastic price on Bookabach.
Are there holiday homes with WiFi in Bennington?
There are 175 holiday homes with WiFi in Bennington. If you want to disconnect from the world on your trip, but still need to be connected to the web, these properties have what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Bennington?
You can choose from 237 Bookabach holiday homes with air conditioning in Bennington offering that cooling breeze and extra element of comfort. Just enter your preferred dates of travel and then use our handy filters to find stays with air conditioning.
How old do you have to be to rent a holiday home in Bennington?
The minimum age permitted can differ between properties on Bookabach, so be sure to check the rules of the holiday home in Bennington you want to book. But normally, it’s 16, 18 or 21.
How long can I rent a holiday home in Bennington for?
The amount of time you can stay in a Bennington holiday home for depends on each property. Simply put in your preferred travel dates to browse options offering extended stays. They come with all you require to make your extended holiday more comfortable and convenient, like air conditioning and laundries. Some Bookabach holiday homes may also offer weekly or monthly discounted prices, so you can stay even longer for less.

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