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

Bennington Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Bennington holiday 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

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 HK$1,153
HK$3,294 total
includes taxes & fees
19 Oct - 20 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
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

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.
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
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, (10 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 HK$911
HK$1,609 total
includes taxes & fees
29 Oct - 30 Oct
Cozy Home in Pownal VT
A dirt bike trail in a forested area.

4. 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 HK$2,786
HK$3,463 total
includes taxes & fees
20 Oct - 21 Oct
Long Trail House at Stratton Mountain Resort
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 HK$1,518
HK$2,131 total
includes taxes & fees
21 Oct - 22 Oct
Spacious apartment in beautiful, historic Arlington VT
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

Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
Sandgate
The price is HK$1,753
HK$2,263 total
includes taxes & fees
20 Oct - 21 Oct
Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

7. 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 HK$585
HK$1,770 total
includes taxes & fees
29 Oct - 30 Oct
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Terrace/patio

8. 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 HK$1,916
HK$5,125 total
includes taxes & fees
28 Oct - 29 Oct
The Birchwood Cabin - Stunning Mountain Views
A playground with slides and climbing structures surrounded by trees.

9. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (21 reviews)
"Nice place "
United States
Janja L.
The price is HK$1,010
HK$2,952 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Bromley Retreat
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

10. 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 HK$898
HK$3,143 total
includes taxes & fees
3 Nov - 4 Nov
Historic Home with Colonial Charm in Manchester
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

11. 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 HK$585
HK$2,009 total
includes taxes & fees
25 Oct - 26 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

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

Lovely ski-in/out condo steps from ski lift with trails and amazing views
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 HK$585
HK$2,462 total
includes taxes & fees
30 Oct - 31 Oct
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A white building with green shutters, a covered porch, and a landscaped garden with flowers.

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

ADA King Room w/ Roll-In Shower & Views
Manchester Village Historic District
The price is HK$1,616
HK$1,955 total
includes taxes & fees
4 Nov - 5 Nov
ADA King Room w/ Roll-In Shower & Views
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

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

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very good, (1 review)
The price is HK$1,096
HK$3,179 total
includes taxes & fees
30 Oct - 31 Oct
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

15. 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 HK$1,172
HK$3,497 total
includes taxes & fees
3 Nov - 4 Nov
Modern Mountain Retreat w/ Chef’s Kitchen
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, (2 reviews)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
The price is HK$2,119
HK$4,833 total
includes taxes & fees
19 Oct - 20 Oct
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

17. 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.
The price is HK$1,271
HK$3,671 total
includes taxes & fees
19 Oct - 20 Oct
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A living room with a television, sofa, and coffee table.

18. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (6 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 HK$1,624
HK$3,839 total
includes taxes & fees
25 Oct - 26 Oct
Long Trail House South Wing 2B2B Condo
An outdoor dining area with a wooden deck, a table set with plates, glasses, and a vase of flowers.

19. Tranquil Brookside Retreat with Hot Tub & Firepit

Tranquil Brookside Retreat with Hot Tub & Firepit
Peru
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
The price is HK$1,912
HK$5,461 total
includes taxes & fees
1 Nov - 2 Nov
Tranquil Brookside Retreat with Hot Tub & Firepit
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

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

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (43 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is HK$1,549
HK$5,203 total
includes taxes & fees
19 Oct - 20 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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
"Overnight stay Nice break from a long drive."
Randy 1-night trip
Posted 3 days 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:

  • 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 holiday rental in Bennington?

Yes, there are holiday rentals in Bennington close to Bennington Center for the Arts, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Bennington has to offer?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of Bennington is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Bennington?

With 16 Expedia holiday rentals, you're guaranteed 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 holiday rental in Bennington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bennington. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.