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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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 ￥21,098
￥51,204 total
includes taxes & fees
Sep 21 - Sep 22
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A room with wooden walls, a window with a view of the sky and greenery, a hanging macrame wall decoration, and a vase with flowers on the windowsill.

2. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Laurie was an amazing host, with an amazing property! What an adorable home with an adorable view."
United States
Michaela J.
The price is ￥15,472
￥38,683 total
includes taxes & fees
Sep 22 - Sep 23
Peaceful getaway at birds of a feather
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, (9 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is ￥16,738
￥29,073 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Home in Pownal VT
A red house with a porch, surrounded by a grassy yard and trees.

4. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is ￥19,791
￥61,907 total
includes taxes & fees
Sep 21 - Sep 22
Two Brooks Lodge

5. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (65 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
The price is ￥27,923
￥38,224 total
includes taxes & fees
Sep 21 - Sep 22
Spacious apartment in beautiful, historic Arlington VT
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

6. 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
The price is ￥22,450
￥64,740 total
includes taxes & fees
Sep 21 - Sep 22
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

7. 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 ￥47,597
￥109,845 total
includes taxes & fees
Sep 23 - Sep 24
The Birchwood Cabin - Stunning Mountain Views
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

8. Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
Manchester
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful cozy house with plenty of beds and space. We drove here in a snowstorm and were so thankful that the host had cleared the driveway and walkways for us. Overall a great stay."
United States
Greg W.
The price is ￥52,356
￥79,149 total
includes taxes & fees
Sep 22 - Sep 23
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

9. 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, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is ￥52,868
￥65,715 total
includes taxes & fees
Sep 28 - Sep 29
Long Trail House at Stratton Mountain Resort
A large indoor swimming pool with wooden beams and a central decorative structure.

10. Spacious 2BR Suite with Fireplace & Kitchen

Spacious 2BR Suite with Fireplace & Kitchen
Manchester Village Historic District
The price is ￥132,481
￥167,115 total
includes taxes & fees
Sep 20 - Sep 21
Spacious 2BR Suite with Fireplace & Kitchen
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

11. 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 ￥25,871
￥72,533 total
includes taxes & fees
Sep 20 - Sep 21
Modern Mountain Retreat w/ Chef’s Kitchen
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

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

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is ￥11,565
￥34,817 total
includes taxes & fees
Sep 28 - Sep 29
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A large indoor swimming pool with wooden beams and a central decorative structure.

13. Equinox Getaway | Queen Guest Room w/ Sauna & Spa

Equinox Getaway | Queen Guest Room w/ Sauna & Spa
Manchester Village Historic District
The price is ￥50,417
￥63,172 total
includes taxes & fees
Sep 27 - Sep 28
Equinox Getaway | Queen Guest Room w/ Sauna & Spa
A large white building with green shutters, a central entrance, and a surrounding lawn.

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

ADA King Room w/ Roll-In Shower & Views
Manchester Village Historic District
The price is ￥49,072
￥61,926 total
includes taxes & fees
Sep 22 - Sep 23
ADA King Room w/ Roll-In Shower & Views
A two-story white house with a front porch, a door with a wreath, and a chimney.

15. Cozy farmhouse in Manchester - short drive to multiple ski mountains!

Cozy farmhouse in Manchester - short drive to multiple ski mountains!
Manchester
9.4 out of 10, Exceptional, (3 reviews)
"The hosts were very friendly and responsive during our stay. Loved that the house is close to the main town as well as close to the ski slopes (Bromley). "
United States
Marissa H.
The price is ￥58,639
￥114,819 total
includes taxes & fees
Sep 29 - Sep 30
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

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

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is ￥11,565
￥39,726 total
includes taxes & fees
Sep 20 - Sep 21
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A cabin with a triangular roof, a wooden deck, and a front porch.

17. The Vermont A-Frame Mountain Retreat

The Vermont A-Frame Mountain Retreat
Winhall
9.8 out of 10, Exceptional, (29 reviews)
"Great home, perfect weekend away at Stratton. Host was great and so was the property"
United States
Kevin M.
The price is ￥27,005
￥84,925 total
includes taxes & fees
Sep 23 - Sep 24
The Vermont A-Frame Mountain Retreat
A red barn, a hammock, a fire pit, and a chair in a grassy area with trees and a stream in the background.

18. 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 ￥35,016
￥45,301 total
includes taxes & fees
Sep 30 - Oct 1
Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

19. 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, (34 reviews)
"Great space, great location!"
United States
Jason S.
The price is ￥24,614
￥68,962 total
includes taxes & fees
Sep 21 - Sep 22
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

20. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
The price is ￥61,897
￥79,936 total
includes taxes & fees
Sep 22 - Sep 23
Spectacular Cottage with Swimming Pool and Foosball in Stratton, 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

Hampton Inn Bennington

Hampton Inn Bennington

8/10 Good
"We were on the third floor which had been completely renovated. Everything was like brand new. The lobby was another story. The lobby was in the process of being renovated which was messy. The continental breakfast was sparse compared to other Hampton Inn’s we have stayed at."
Tony 1-night trip
Posted 11 hours ago
Hampton Inn Bennington

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:

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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.