Bennington Vacation Rentals from $441: Search Short-Term Rentals

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Our top choices for Bennington vacation rentals

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

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

Bennington

Malika R.

A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

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

Woodford

Dana W.

$481 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

3. Cozy Home in Pownal VT

Pownal

Jeri R.

$174 nightly

Nov 8 - Nov 9

Total with taxes and fees

A covered porch with wooden beams, a pool, and chairs.

4. West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub

Bennington

$245 nightly

Nov 5 - Nov 6

Total with taxes and fees

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

5. Long Trail House at Stratton Mountain Resort

Stratton

Michael

$391 nightly

Nov 5 - Nov 6

Total with taxes and fees

A snow-covered landscape with a cabin surrounded by trees.

6. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

Pownal

Claudette R.

$525 nightly

Nov 5 - Nov 6

Total with taxes and fees

7. Spacious apartment in beautiful, historic Arlington VT

Arlington

Mike K.

$231 nightly

Nov 5 - Nov 6

Total with taxes and fees

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

8. Long Trail House 368 condo in Stratton Village, walk to the lifts

Stratton

$232 nightly

Nov 5 - Nov 6

Total with taxes and fees

A building with a sign reading 'Landmark' and a large spherical sculpture in the center.

9. Fourth-floor Stratton Village studio with valley-view balcony

Stratton

$205 nightly

Nov 5 - Nov 6

Total with taxes and fees

A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

10. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

Stratton

eric m.

$283 nightly

Nov 5 - Nov 6

Total with taxes and fees

A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

11. Historic Home with Colonial Charm in Manchester

Manchester

Victor G.

$332 nightly

Nov 10 - Nov 11

Total with taxes and fees

12. East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

Bennington

$245 nightly

Nov 5 - Nov 6

Total with taxes and fees

13. The Birchwood Cabin - Stunning Mountain Views

Sunderland

Robert V.

$606 nightly

Nov 16 - Nov 17

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a clear sky.

14. Cozy Bromley Retreat — Ski-In, Ski-Out

Bromley Mountain

Andrew P.

$383 nightly

Nov 5 - Nov 6

Total with taxes and fees

A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

15. Founders Lodge condo at Stratton Mountain with gas fireplace

Stratton

$367 nightly

Nov 5 - Nov 6

Total with taxes and fees

A river flowing through a forested area with a grassy bank.

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

Sandgate

$420 nightly

Nov 5 - Nov 6

Total with taxes and fees

A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

17. Modern Mountain Retreat w/ Chef’s Kitchen

Manchester

Eva G.

$360 nightly

Nov 10 - Nov 11

Total with taxes and fees

A room with a large window, a wooden table, two chairs, and a woven basket on the table.

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

Manchester

Peggy S.

$576 nightly

Nov 8 - Nov 9

Total with taxes and fees

A living room with a television, sofa, and coffee table.

19. Long Trail House South Wing 2B2B Condo

Stratton

Eileen R.

$389 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

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

Stratton Mountain

Susan F.

$489 nightly

Nov 5 - Nov 6

Total with taxes and fees

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Top Bennington Hotel Reviews

Hampton Inn Bennington

10/10 Excellent

"Everyone was great. Breakfast was delicious. They all go the extra mile. Thank you! See you in December"

Mountain Sanctuary Dome Rustic Solitude 5BR

8/10 Good

"We had an excellent stay at Nate’s place! Our group loved the architecture and the beautiful scenery. Kitchen tools could have been better, but we managed fine cooking for a group of 8. Plenty of sleeping space for a big group. Would recommend for a weekend away in VT!"

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."

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

10/10 Excellent

"We had a great family getaway here! The hot tub was amazing and the views from the hot tub were perfect. What a beautiful location - quiet, peaceful and a fun space for kids to explore. We had an amazing time trekking out in the woods in the snow.Kitchen was well stocked and the treats, coffee and tea were a nice bonus. My kids enjoyed the extra games as well! Extremely quick responses from the host as well! Thanks for a good time, we are already thinking about coming back in the summer."

Find out more about Bennington

Everything you need to know about Bennington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bennington vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bennington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bennington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bennington. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Bennington in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $441 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bennington rentals

At Expedia, we put the best Bennington vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Bennington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bennington vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bennington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Things to do 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.

Bennington Vacation Rentals

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Check prices for these dates

Our top choices for Bennington vacation rentals

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

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

3. Cozy Home in Pownal VT

4. West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub

5. Long Trail House at Stratton Mountain Resort

6. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

7. Spacious apartment in beautiful, historic Arlington VT

8. Long Trail House 368 condo in Stratton Village, walk to the lifts

9. Fourth-floor Stratton Village studio with valley-view balcony

10. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

11. Historic Home with Colonial Charm in Manchester

12. East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

13. The Birchwood Cabin - Stunning Mountain Views

14. Cozy Bromley Retreat — Ski-In, Ski-Out

15. Founders Lodge condo at Stratton Mountain with gas fireplace

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

17. Modern Mountain Retreat w/ Chef’s Kitchen

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

19. Long Trail House South Wing 2B2B Condo

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

Find vacation rentals that suit your style

Top Bennington Hotel Reviews

Hampton Inn Bennington

Find out more about Bennington

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