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

Our top choices for Bennington vacation rentals

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

1. 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 AED 460
AED 2,062 total
includes taxes & fees
16 Nov - 17 Nov
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.

2. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (12 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 AED 426
AED 749 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Home in Pownal VT
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

3. 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 AED 1,304
AED 1,621 total
includes taxes & fees
28 Oct - 29 Oct
Long Trail House at Stratton Mountain Resort
Exterior

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

East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
Bennington
The price is AED 1,194
AED 1,530 total
includes taxes & fees
28 Oct - 29 Oct
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
Property grounds

5. 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 AED 711
AED 994 total
includes taxes & fees
28 Oct - 29 Oct
Spacious apartment in beautiful, historic Arlington VT
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

6. 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 AED 274
AED 941 total
includes taxes & fees
2 Nov - 3 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts
A building with a sign reading 'Landmark' and a large spherical sculpture in the center.

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

Fourth-floor Stratton Village studio with valley-view balcony
Stratton
The price is AED 274
AED 824 total
includes taxes & fees
29 Oct - 30 Oct
Fourth-floor Stratton Village studio with valley-view balcony
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, (36 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 AED 274
AED 1,152 total
includes taxes & fees
28 Oct - 29 Oct
Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

9. 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 AED 396
AED 1,444 total
includes taxes & fees
28 Oct - 29 Oct
Historic Home with Colonial Charm in Manchester
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a clear sky.

10. Cozy Bromley Retreat

Cozy Bromley Retreat
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 AED 473
AED 1,595 total
includes taxes & fees
1 Nov - 2 Nov
Cozy Bromley Retreat
Terrace/patio

11. 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 AED 1,603
AED 3,309 total
includes taxes & fees
19 Nov - 20 Nov
The Birchwood Cabin - Stunning Mountain Views
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 AED 513
AED 1,492 total
includes taxes & fees
28 Oct - 29 Oct
Founders Lodge condo at Stratton Mountain with gas fireplace
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

13. 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)
"Great space, great location!"
United States
Jason S.
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A living room with a television, sofa, and coffee table.

14. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (7 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 AED 684
AED 1,699 total
includes taxes & fees
3 Nov - 4 Nov
Long Trail House South Wing 2B2B Condo
A river flowing through a forested area with a grassy bank.

15. 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
The price is AED 1,319
AED 1,700 total
includes taxes & fees
28 Oct - 29 Oct
Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
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 AED 992
AED 2,262 total
includes taxes & fees
29 Oct - 30 Oct
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A large indoor swimming pool with wooden beams and a central decorative structure.

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

ADA King Room w/ Roll-In Shower & Views
Manchester Village Historic District
The price is AED 851
AED 1,019 total
includes taxes & fees
9 Nov - 10 Nov
ADA King Room w/ Roll-In Shower & Views
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

18. 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 AED 552
AED 1,641 total
includes taxes & fees
28 Oct - 29 Oct
Modern Mountain Retreat w/ Chef’s Kitchen
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

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

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.2 out of 10, Wonderful, (44 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is AED 725
AED 2,718 total
includes taxes & fees
28 Oct - 29 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A cozy living room with a sofa, coffee table, and dining area. A ceiling fan is visible, and there are skis leaning against the wall.

20. Two bedroom Condo With Mountain View And Fireplace

Two bedroom Condo With Mountain View And Fireplace
Stratton
9.2 out of 10, Wonderful, (5 reviews)
"Very comfortable stay for four adults. The kitchen is well appointed, great beds and showers. Easy, prompt communication with owner. "
United States
Marie B.
The price is AED 830
AED 2,494 total
includes taxes & fees
1 Nov - 2 Nov
Two bedroom Condo With Mountain View And Fireplace
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

Hampton Inn Bennington

Hampton Inn Bennington

10/10 Excellent
"Breakfast had cooked oatmeal And had 3 main items for breakfast each day"
paul 2-night trip
Posted 2 days ago
Hampton Inn 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.