Bennington Vacation Rentals from ￥35,466: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Bennington vacation rentals

A bedroom with a bed, bedside tables, a window, and a radiator.

1. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Woodford

Dana W.

￥65,352 total

includes taxes & fees

Oct 20 - Oct 21

A two-story house with a porch, surrounded by trees and snow.

2. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Bennington

Malika R.

￥54,075 total

includes taxes & fees

Oct 20 - Oct 21

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

3. Cozy Home in Pownal VT

Pownal

Jeri R.

￥32,405 total

includes taxes & fees

Oct 20 - Oct 21

A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

4. Long Trail House at Stratton Mountain Resort

Stratton

Michael

￥69,730 total

includes taxes & fees

Oct 20 - Oct 21

5. Spacious apartment in beautiful, historic Arlington VT

Arlington

Mike K.

￥42,920 total

includes taxes & fees

Oct 21 - Oct 22

A red barn, a hammock, a fire pit, and a chair in a grassy area with trees and a stream in the background.

6. Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont

Sandgate

￥45,358 total

includes taxes & fees

Oct 20 - Oct 21

A building with a sign reading 'Fire Tower Restaurant & Tavern.'

7. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Stratton

￥35,466 total

includes taxes & fees

Oct 22 - Oct 23

8. The Birchwood Cabin - Stunning Mountain Views

Sunderland

Robert V.

￥99,590 total

includes taxes & fees

Oct 28 - Oct 29

View all properties

Find vacation rentals that suit your style

Cabins

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Bennington Hotel Reviews

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

10/10 Excellent

"Perfect location - walking distance to restaurants and shops. Chris was very responsive and helpful! Will definitely stay here again even visiting my son."

Knotty Pine

8/10 Good

"I felt a little abandoned by the manager because she had very limite hours when she was available. The was pleasant and responsive when we did see her, but . . . Bathroom was clean and all, but design didn't allow space for a woman to lay out makeup and personal items. Very limited. Beds were very comfortable. Glad to have frig and microwave."

Perfect for a peaceful get away in clean fresh Vermont air!

10/10 Excellent

"We had such an enjoyable and peaceful get away at the Honey Bear Cabin! It was so warm and inviting right from entering the cabin with its warm, cozy atmosphere. Waking up and enjoying the sunrise on the pond with a great cup of coffee was the best! The bed was so comfy and the decor was rustic and adorable. We felt like it was a little peace of heaven with the beautiful pond, bees and dragonflies surrounding the property. LindaJane was an exceptional and thoughtful host. She made our 40th wedding anniversary very special. The communication was prompt and LindaJane checked into make sure our stay was comfortable and enjoyable. Our dog Luna loved the dog toys and snacks that were supplied by Linda and she loved her walks amongst the property and country road. We’re so glad we had such a relaxing and fun time! We’ll definitely be back!"

Starlight Inn

8/10 Good

"Very nice old school Vermont motor inn. Dated decor, but all clean and well maintained. Except the shower. The shower was clean, but even with only a few people in the motel getting consistent hot/cold water was difficult. Literally our only complaint. Very good location to downtown, too. Only about 4 1/2 miles from Bennington College if you are visiting."

Find out more about Bennington

Search for holiday rentals in Bennington on Expedia! You can easily find your home rentals, villas, holiday apartments in Bennington using one of the methods below:

View our selection of featured holiday rentals in Bennington
Use the map to find apartments and other holiday homes in the Bennington neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Bennington while they last

Look no further and take a look at our great range of rental properties in Bennington!

Frequently asked questions

Can I find a vacation rental in Bennington?

Yes, we have vacation rentals in Bennington close to Bennington Center for the Arts, or you can select a more remote option if you'd like a relaxing place to stay. Tourists who visit Bennington speak highly of the ski slopes and array of shops. While you're in the area, you can also enjoy the majestic mountain landscape and museums.

What are some of the best vacation rentals in Bennington?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: Visitors like this Bennington vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Bennington?

With 16 Expedia vacation rentals, you're sure to find just the right place for your Bennington stay.

What’s there to see and do in Bennington?

Enjoy the outdoors at Green Mountain National Forest and Harmon Hill, or simply take in cultural attractions like Bennington Museum and Robert Frost Stone House Museum. While here, Prospect Mountain Cross-Country Ski Center and Woodford State Park are other places worth a visit.

What’s a vacation rental in Bennington like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Bennington. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family trip.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Bennington vacation rentals

1. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

2. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

3. Cozy Home in Pownal VT

4. Long Trail House at Stratton Mountain Resort

5. Spacious apartment in beautiful, historic Arlington VT

6. Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont

7. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

8. The Birchwood Cabin - Stunning Mountain Views

9. Cozy Bromley Retreat

10. Historic Home with Colonial Charm in Manchester

11. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

12. Lovely ski-in/out condo steps from ski lift with trails and amazing views

13. ADA King Room w/ Roll-In Shower & Views

14. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

15. Modern Mountain Retreat w/ Chef’s Kitchen

16. Cozy 3 Bedroom Condo in the Heart of Manchester VT

17. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

18. Long Trail House South Wing 2B2B Condo

19. Tranquil Brookside Retreat with Hot Tub & Firepit

20. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Find vacation rentals that suit your style

Top Bennington Hotel Reviews

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Hampton Inn Bennington

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Knotty Pine

South Shire

Perfect for a peaceful get away in clean fresh Vermont air!

Starlight Inn

Cozy Loft steps from VT Downtown

The Four Chimneys Inn

Find out more about Bennington

Frequently asked questions

Go further with the Expedia app