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Bennington holiday lettings

We found 936 holiday rentals — enter your dates for availability

Discover a selection of 1,000 holiday rentals in Bennington that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including internet/WiFi and pool. Prices start at £ 132 per night, and houses and cabins are popular options for a stay in Bennington. Either way, you'll find a rental for everyone's needs.
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Find the best place to stay — Bennington

Romantic Private Vermont Cottage, dogs welcome

Sleeps 4 · 1 Bedroom · 1 Bathroom
£ 202 avg/night
(122)

Cozy Converted Barn on Secluded 6.5 acres

Sleeps 8 · 1 Bedroom · 1 Bathroom
£ 152 avg/night
(127)

Victorian Home in Bennington, Vermont

Sleeps 7 · 3 Bedrooms · 3 Bathrooms
£ 284 avg/night
(33)

Two Brooks Lodge - Beautiful Waterfront Vermont Retreat

Sleeps 6 · 3 Bedrooms · 1 Bathroom
£ 132 avg/night

Great Place to get away and have clean fresh air surround you!

Sleeps 6 · 1 Bedroom · 1 Bathroom
£ 175 avg/night
(91)

Bennington Guest Farmhouse

Sleeps 9 · 5 Bedrooms · 2 Bathrooms
£ 195 avg/night
(15)

Search 936 holiday rentals

Top rated rentals — Bennington
Stayed Mar 2021

Beautiful historic getaway

What a find! A beautiful historic home with a covered bridge just across the street. The hosts were gracious and responsive. We really enjoyed exploring the area, hiking, and Mass MOCA. They really left no detail out. From hammock to lights and firep...

Cindy K.
Cindy K.
Stayed Feb 2021

Hiking in the Green Mountains

We stayed at the Cloud Compound for 3 nights. What a perfectly sized little space for two hikers. The accommodations were very comfortable and perfect to come back to after a long day of hiking/ice fishing/ winter activities. And there were fresh e...

Elena R.
Elena R.
Stayed Feb 2021

Winter Wonderland

Ideally located near great cross country ski area. The property was comfortable, extremely well-stocked with whatever we might have needed in the kitchen and bathroom. Linda Jane was always helpful and easy to deal with. The contemporary fireplace ke...

Ronald S.
Ronald S.
Stayed Feb 2021

AMAZING!!

We just had the most perfect long weekend getaway at Lars’ place. Everything was just as described and even better than I could’ve expected. It’s such a great location to get away from it all but also close enough to other areas if you want to do mor...

Sandra L.
Sandra L.
Stayed Feb 2021

Beautiful Bennington

This is our 2nd time staying in this beautiful home, and we will certainly be back. The house is spacious, very clean, and has everything you need. We were an easy 30 minutes to Mt. Snow, and got to enjoy the great vibe of Bennington. Excellent commu...

ashley z.
ashley z.
Stayed Jan 2021

Perfect cozy cabin!

This cabin was so cute and much more spacious than expected. It had everything you could possibly need and the neighborhood was gorgeous after a fresh 2 feet of snow! We loved the wood burning stove. Stephanie was available for all our questions and ...

Arianna R.
Arianna R.
Stayed Dec 2020

Perfect for families

We had a really great stay at the Penthouse. It’s often hard to find a big enough space to stay with our teens, but this was perfect! We had plenty of space and the space had everything needed. The kitchen is fully stocked, there are laundry faciliti...

Courtney M.
Courtney M.
Stayed Dec 2020

Easy-going relaxing trip

Our family really enjoyed our stay at the property. The house was very clean upon arrival and the location was convenient to stores, activities, and parks. The kids loved the swing set and running in the spacious backyard. The thermostat worked great...

Anna D.
Anna D.
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Destination guide

Why people love visiting friendly Bennington

The area's museums and monuments are just some of the reasons to come on holiday to Bennington. Well known for its shopping, university setting and restaurants, this welcoming city won't disappoint. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities

Activities and attractions in Bennington

Are you looking for attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that makes Bennington a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Prospect Mountain Cross-Country Ski Center (6.1 mi / 9.8 km)
  • Clarksburg State Park (11.7 mi / 18.9 km)
  • Waubeeka Golf Links (15.4 mi / 24.9 km)
  • Haystack Golf and Country Club (15.7 mi / 25.3 km)
  • Mount Snow (16.6 mi / 26.8 km)
  • Mount Snow Golf Course (17.2 mi / 27.7 km)
Natural features

Exploring the natural landscape of Bennington

Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Bennington. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Harmen Hills Trail (4.1 mi / 6.7 km)
  • Howard Park (4.9 mi / 7.8 km)
  • Lake Shaftsbury State Park (10 mi / 16.1 km)
  • Clarksburg State Park (11.7 mi / 18.9 km)
  • Natural Bridge State Park (13.2 mi / 21.3 km)
  • Western Gateway Heritage State Park (13.3 mi / 21.5 km)
How to get there

How to get to and around Bennington

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 31.7 mi (51 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Albany, NY (ALB-Albany Intl.), which is 32.4 mi (52.1 km) away.

Can I find a vacation rental around Bennington?

Yes, our 2021 property listings offer a large selection of 936 vacation rentals near Bennington. From 660 houses to 102 cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Bennington for a holiday or a weekend are on Vrbo.