Bennington Vacation Rentals

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Vacation 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.
$404 nightly
The price is $453
Dec 2 - Dec 3
Total with taxes and fees
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.
$378 nightly
The price is $404
Nov 30 - Dec 1
Total with taxes and fees
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.
$256 nightly
The price is $272
Dec 14 - Dec 15
Total with taxes and fees
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
House (1 Bedroom) | 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 traveler
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
House (2 Bedrooms) | 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
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
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
$409 nightly
The price is $462
Nov 30 - Dec 1
Total with taxes and fees
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.
$687 nightly
The price is $776
Dec 3 - Dec 4
Total with taxes and fees
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.
$247 nightly
The price is $279
Nov 30 - Dec 1
Total with taxes and fees
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

Hampton Inn Bennington

Hampton Inn Bennington

10/10 Excellent
"Friendly staff, clean comfortable room, great location."
Sam 1-night trip
Posted 3 days ago
Hampton Inn Bennington

Find out more about Bennington

Everything you need to know about Bennington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bennington vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bennington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bennington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bennington. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Bennington in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $272 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bennington rentals

At Expedia, we put the best Bennington vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Bennington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bennington vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bennington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Bennington?

Yes, we have vacation rentals close to popular attractions in Bennington, or you can go with a more secluded option if you want 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?

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable: Visitors like this Bennington vacation home rental. It is located in the city center 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals will I find in Bennington?

With 15 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 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 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.