Bennington Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Bennington

Property grounds
Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!

Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!

Woodford
10.0 out of 10, Exceptional, (1)
"This Cozy Cabin was amazing. Chris and Nicole were great hosts who were very responsive and courteous to make our trip as relaxing as we needed. They left detailed instructions on how the place operated and made sure the place was ready to go for when we arrived. If you want to get away for some peace and quiet whether it be for a day or a week, I highly recommend this spot. We would absolutely book with them again!! "
United States
Evan M.
The price is HK$2,202
HK$3,520 total
includes taxes & fees
2 Dec - 3 Dec
Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!
Exterior
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Woodford
8.8 out of 10, Excellent, (3)
"Perfect cottage on the water!! Enjoyed kayaking and pedal boat with family. Beautiful greenery! Very quick respond."
United States
Elzbieta M.
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Smart TV, fireplace
Lake life at Woodford Cottage

Lake life at Woodford Cottage

Bennington
9.6 out of 10, Exceptional, (15)
"We enjoyed our time at this cottage. Well-equipped, clean and comfortable. Very private and located just outside Bennington and not too far from the art scene in Williamstown and North Adams."
United States
Mary D.
Lake life at Woodford Cottage
Outdoor dining
Green Mountain Getaway

Green Mountain Getaway

2.0 star property
Bennington
9.6 out of 10, Exceptional, (18)
"Great one night stay for a work trip. Common living space and bedrooms are very large. Very clean especially the bathroom. "
United States
Robyn H.
The price is HK$1,602
HK$3,139 total
includes taxes & fees
30 Nov - 1 Dec
Green Mountain Getaway
Interior
Mountain Sanctuary Dome Rustic Solitude 5BR

Mountain Sanctuary Dome Rustic Solitude 5BR

Pownal
9.6 out of 10, Exceptional, (9)
"The facilities were as described; everything that was needed was easily accessible. When we couldn't find something, Nate was on hand to give us the guidance we needed."
United States
Cyndi L.
Mountain Sanctuary Dome Rustic Solitude 5BR
Fridge, microwave, oven, stovetop
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

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

Bennington
8.6 out of 10, Excellent, (34)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
United States
Ransom W.
The price is HK$778
HK$2,113 total
includes taxes & fees
14 Dec - 15 Dec
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Interior
Bennington Gem w/ Smart TV Near Historic District!

Bennington Gem w/ Smart TV Near Historic District!

3.0 star property
Bennington
8.0 out of 10, Very good, (2)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
United States
Anonymous traveller
Bennington Gem w/ Smart TV Near Historic District!
Interior
Meme's High Mountain Lake House

Meme's High Mountain Lake House

Woodford
10.0 out of 10, Exceptional, (9)
"We stayed in the house for 3 nights and it felt like being at home. It is a quiet place with beautiful lake view. The kitchen has all you need. Thank you, Jessica for a nice welcome gift!"
United States
Nataliya K.
Meme's High Mountain Lake House
Outdoor dining
VT at its best! Near hiking trails, museums & colleges.

VT at its best! Near hiking trails, museums & colleges.

Bennington
10.0 out of 10, Exceptional, (1)
"The property was even more beautiful than the detailed photos depicted. It is secluded and private and yet, only a short drive to downtown.The interior finishes were homey and classy at the same time.Courtney is a fantastic host, who communicated thoroughly and responded promptly.If you’re looking for a quiet get away, you will love this property. "
United States
Kyle W.
VT at its best! Near hiking trails, museums & colleges.
Exterior
Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!

Woodford
10.0 out of 10, Exceptional, (77)
"We had an absolutely incredible vacation staying at Linda's cabin right on Big Pond. Having all the boats to use was great, our dog loved swimming everyday, and Linda was the best host"
United States
Cathy G.
Perfect for a peaceful get away in clean fresh Vermont air!
Smart TV, books
Charming 2-bedroom apartment in superb Bennington with WiFi

Charming 2-bedroom apartment in superb Bennington with WiFi

Bennington
9.6 out of 10, Exceptional, (4)
"The pictures don’t do the listing justice, much bigger than the puctures suggest. The location is great with minutes away from Main St. (bars restaurants). Robin is also a great host! Really enjoyed our stay look forward to booking again next winter "
United States
Marvin J.
Charming 2-bedroom apartment in superb Bennington with WiFi
Exterior
Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Bennington
10.0 out of 10, Exceptional, (4)
"The apartment was even better than the pictures. The beds were very comfortable and the location was excellent for walking around. There is no other place anyone should stay in Bennington besides this place."
United States
Dustin M.
Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown
Interior
Breathtaking Mtn Views: Stylish Rustic Retreat!

Breathtaking Mtn Views: Stylish Rustic Retreat!

3.0 star property
Bennington
Breathtaking Mtn Views: Stylish Rustic Retreat!
Property grounds
Modern Woodford Estate, Lake, Mountain, VAST entrance

Modern Woodford Estate, Lake, Mountain, VAST entrance

Woodford
Modern Woodford Estate, Lake, Mountain, VAST entrance
Pool
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, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is HK$2,919
HK$3,629 total
includes taxes & fees
11 Dec - 12 Dec
Long Trail House at Stratton Mountain Resort
Outdoor spa tub
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Jamaica
9.6 out of 10, Exceptional, (21)
"House was perfect and just what we were looking for! Very clean, great hot tub, loved the fire pit!Cassie was incredibly helpful with local recommendations and going above and beyond!Highly recommend!"
United States
Neal T.
The price is HK$1,608
HK$6,035 total
includes taxes & fees
3 Dec - 4 Dec
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Fridge, microwave, oven, stovetop
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Sunderland
10.0 out of 10, Exceptional, (127)
"Lovely home with beautiful view! Excellent host. We had a wonderful stay. "
United States
Julia P.
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
TV, fireplace
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
8.6 out of 10, Excellent, (27)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
The price is HK$552
HK$2,173 total
includes taxes & fees
30 Nov - 1 Dec
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Dining
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Winhall
9.6 out of 10, Exceptional, (241)
"As this represents our second stay at the Honeymoon Cottage we are already talking another trip to Winhall. Needless to say we enjoy the rustic appeal and location, with close proximity to the AT and Vermont’s Long Trail; close enough to Manchester for dinner; or tours of the Orvis fly rod factory, American Fly Fishing Museum or Hildene"
United States
E. David B.
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Interior
Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved

Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved

Manchester
10.0 out of 10, Exceptional, (58)
"Great place for a big group. Kids loved exploring and parents loved the space."
United States
John L.
Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved
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

Knotty Pine

Knotty Pine

10/10 Excellent
"We stayed in room 19. It was very clean and worth the money. "
Chris 2-night trip
Posted 9 days ago
Knotty Pine

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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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 close to the most popular sights in Bennington, 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?

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable: This holiday home rental outside of Bennington is located in the city centre, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals will I find in Bennington?

With 15 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 Harmen Hills Trail, or simply take in cultural attractions like Bennington Museum and Robert Frost Stone House Museum. While here, Old First Congregational Church and Bennington Battle Monument 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.