A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is ￥20,010
￥45,446 total
includes taxes & fees
Nov 3 - Nov 4
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
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

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is ￥18,482
￥82,607 total
includes taxes & fees
Nov 9 - Nov 10
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

3. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (13 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
The price is ￥18,293
￥30,723 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Home in Pownal VT
Exterior

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

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

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (85 reviews)
"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."
United States
Michael
The price is ￥55,934
￥69,526 total
includes taxes & fees
Nov 3 - Nov 4
Long Trail House at Stratton Mountain Resort
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

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

Fourth-floor Stratton Village studio with valley-view balcony
Stratton
The price is ￥13,200
￥35,802 total
includes taxes & fees
Nov 3 - Nov 4
Fourth-floor Stratton Village studio with valley-view balcony
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

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

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is ￥13,200
￥40,609 total
includes taxes & fees
Nov 3 - Nov 4
Long Trail House 368 condo in Stratton Village, walk to the lifts
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

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

Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
Stratton
8.4 out of 10, Very good, (37 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is ￥13,200
￥49,511 total
includes taxes & fees
Nov 3 - Nov 4
Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
Property grounds

9. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (66 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
The price is ￥30,488
￥40,854 total
includes taxes & fees
Nov 3 - Nov 4
Spacious apartment in beautiful, historic Arlington VT
A snow-covered landscape with a cabin surrounded by trees.

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

Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
Pownal
10.0 out of 10, Exceptional, (41 reviews)
"We enjoyed our stay! The home was clean, well-stocked, and very comfortable. I loved the serenity of the location. We took walks on trails through the forest and enjoyed the peace and quiet."
United States
Claudette R.
The price is ￥49,631
￥92,645 total
includes taxes & fees
Nov 5 - Nov 6
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
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

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were absolutely amazing. We had a wonderful time. The home is beautiful. The host is very communicative."
United States
Victor G.
The price is ￥17,002
￥59,272 total
includes taxes & fees
Nov 3 - Nov 4
Historic Home with Colonial Charm in Manchester
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

12. Founders Lodge condo at Stratton Mountain with gas fireplace

Founders Lodge condo at Stratton Mountain with gas fireplace
Stratton
8.0 out of 10, Very good, (1 review)
The price is ￥24,727
￥64,653 total
includes taxes & fees
Nov 3 - Nov 4
Founders Lodge condo at Stratton Mountain with gas fireplace
A playground with slides and climbing structures surrounded by trees.

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

Cozy Bromley Retreat — Ski-In, Ski-Out
Bromley Mountain
9.4 out of 10, Exceptional, (21 reviews)
"The place was clean and had all the essentials. Right across from pool and great stay."
United States
Andrew P.
The price is ￥22,649
￥68,179 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Bromley Retreat — Ski-In, Ski-Out
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

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

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (37 reviews)
"Excellent place! Impeccable!"
United States
Susan F.
The price is ￥30,652
￥85,201 total
includes taxes & fees
Nov 4 - Nov 5
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A living room with a television, sofa, and coffee table.

15. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (8 reviews)
"Very clean 2br 2ba condo in excellent location. Host provided detailed important information that helped us find property and how to access unit. I would definitely recommend staying here."
United States
Eileen R.
The price is ￥29,353
￥69,312 total
includes taxes & fees
Nov 8 - Nov 9
Long Trail House South Wing 2B2B Condo
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

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

Cozy 3 Bedroom Condo in the Heart of Manchester VT
Manchester
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful accommodations. Great communication with host."
United States
Peggy S.
The price is ￥42,541
￥91,697 total
includes taxes & fees
Nov 3 - Nov 4
Cozy 3 Bedroom Condo in the Heart of Manchester VT
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

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
10.0 out of 10, Exceptional, (1 review)
"Communication with Caroline was top notch and speedy! Very clear instructions for accessing the property and check out. Even though this place is connected with two other rooms/units ( I think that is what it is) we never heard them and hopefully we didn't bother them either!The house was amazing inside and out. The location was exceptional!Thank you for a beautiful stay!"
United States
Eva G.
The price is ￥21,983
￥65,435 total
includes taxes & fees
Nov 3 - Nov 4
Modern Mountain Retreat w/ Chef’s Kitchen
Terrace/patio

18. The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
Sunderland
10.0 out of 10, Exceptional, (4 reviews)
"Excellent host very responsive. Beautiful cozy cabin with all the amenities you need. Highly recommend! "
United States
Robert V.
The price is ￥39,138
￥99,069 total
includes taxes & fees
Dec 2 - Dec 3
The Birchwood Cabin - Stunning Mountain Views
A large indoor swimming pool with wooden beams and a central decorative structure.

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

ADA King Room w/ Roll-In Shower & Views
Manchester Village Historic District
The price is ￥36,296
￥42,241 total
includes taxes & fees
Nov 23 - Nov 24
ADA King Room w/ Roll-In Shower & Views
A river flowing through a forested area with a grassy bank.

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

Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
Sandgate
Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bennington Hotel Reviews

Bennington Motor Inn

Bennington Motor Inn

8/10 Good
"I had reserved a room in this motel online and we arrived to see adults and children hanging out in front, indicating that it was home for them. Checking in was awkward, as the clerk had to call the owner or manager to check k that we had a reservation. We were wary about staying because of the noise level but were given a room in the back of the hotel and were delighted to find the room was quiet, immaculate, had all the amenities, and was very nicely decorated. The beds were very comfortable and we would stay there again in this part of the motel."
Hilary 1-night trip
Posted 2 days ago
Bennington Motor Inn

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
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  • 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.