Bennington Holiday Rentals

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Holiday Rentals in Bennington

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

Woodford
The price is NZ$787
includes taxes & fees
17 Nov - 18 Nov
Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!

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

Green Mountain Getaway

2.0 star property
Bennington
9.6 out of 10, Exceptional, (17)
"The inside was nice and met our needs. The lawn and landscaping could use some attention. If you love large screen tvs, you will love this house."
United States
Jim K.
The price is NZ$711
includes taxes & fees
17 Nov - 18 Nov
Green Mountain Getaway

Mountain Sanctuary Dome Rustic Solitude 5BR

Pownal
9.6 out of 10, Exceptional, (9)
"My friends and I stayed at the dome home for a weekend during August. The home is as advertised: uniquely constructed and had 6 individual bedrooms. We also loved visiting the swimming hole which is about a 30 minute walk or 4 minute drive from the property. Would recommend planning ahead to minimize driving on and off the property (i.e. get all groceries before arriving) because the road is fairly rocky."
United States
Matthew D.
Mountain Sanctuary Dome Rustic Solitude 5BR

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

Bennington
8.6 out of 10, Excellent, (34)
"We had a lovely stay. The brook on the property is beautiful and peaceful. It was close to town but felt miles away."
United States
Sarah P.
The price is NZ$474
includes taxes & fees
17 Nov - 18 Nov
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Lake life at Woodford Cottage

Bennington
9.6 out of 10, Exceptional, (15)
"Great little cabin. Comfortable for 5-6 people. Quick drive to Mt Snow. Lots of charm!"
United States
K F.
Lake life at Woodford Cottage

Bennington Gem w/ Smart TV Near Historic District!

3.0 star property
Bennington
8.0 out of 10, Very good, (2)
"Two things can improved: 1). The bathroom needs to be renovated. It has a dirty look. 2). The security alarm was beeping irritatingly all the first night. This prevented us from getting anywhere near a good night sleep. I did not find the owner very responsive. He said someone would be there by 4 PM the next day"
United States
Michael
Bennington Gem w/ Smart TV Near Historic District!

Meme's High Mountain Lake House

Woodford
10.0 out of 10, Exceptional, (9)
"We loved this spot! From chilling by the water in the great yard and deck to explore nearby hiking spots, we couldn’t have asked for more! Jessica was very communicative as well. "
United States
Corey V.
Meme's High Mountain Lake House

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.

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

Woodford
10.0 out of 10, Exceptional, (77)
"We came for a 4 day mini-vacation and we couldn’t have selected a better place to stay and get away from it all. We will definitely be back again."
United States
Scott N.
Perfect for a peaceful get away in clean fresh Vermont air!

Charming 2-bedroom apartment in superb Bennington with WiFi

Bennington
9.6 out of 10, Exceptional, (4)
"It was a fine place in fine neighborhood. My only suggestion is the kitchen could be stocked better, for instance there was no toaster. "
United States
Michael B.
Charming 2-bedroom apartment in superb Bennington with WiFi

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Bennington
10.0 out of 10, Exceptional, (4)
"I was sad to leave. My husband called the place "exceptional." It really was a great place to stay.We were looking for a home base for exploring Manchester, Bennington, Williamstown, and North Adams, and this was a perfect location.The apartment itself is fantastic. It was clean and nicely furnished. The bathroom was a delight to use, and the kitchen was well appointed. The beds were so comfortable, and the decor fit the time period of the space while being uncluttered at the same time. The host...
United States
Amanda I.
Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Breathtaking Mtn Views: Stylish Rustic Retreat!

3.0 star property
Bennington
Breathtaking Mtn Views: Stylish Rustic Retreat!

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 NZ$704
includes taxes & fees
17 Nov - 18 Nov
Long Trail House at Stratton Mountain Resort

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

Sunderland
10.0 out of 10, Exceptional, (126)
"I stayed here with 8 people and the house was great for all of us. It was clean and comfortable and the hot tub was an extra plus. I would recommend staying here!"
United States
Alexa S.
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Long Trail House Studio at Stratton Mountain Resort

Stratton
10.0 out of 10, Exceptional, (64)
"Our stay was incredible. The location was perfect, room and facility was clean. Thank you for being a great host, 10/10!"
United States
Tyler M.
Long Trail House Studio at Stratton Mountain Resort

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

Stratton
8.4 out of 10, Very good, (26)
"Great location close to lift. Condo is clean and well appointed."
United States
Grace Ann B.
The price is NZ$490
includes taxes & fees
18 Nov - 19 Nov
Lovely ski-in/out condo steps from ski lift with trails and amazing views

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

Winhall
9.6 out of 10, Exceptional, (241)
"What a wonderful place to stay! My boyfriend and I too advantage of the beautiful deck and had coffee and dinner on it every day. We also used the charcoal grill to cook dinner and the wood stove outside, for a beautiful outside dining expereince! We would love to come back again!"
United States
Katherine B.
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

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

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

Jamaica
9.6 out of 10, Exceptional, (21)
"Good spot for catching up with friends for the weekend. Hot tub was perfect and everything was comfortable."
United States
Ross P.
The price is NZ$1,152
includes taxes & fees
19 Nov - 20 Nov
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
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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Find out more about Bennington

Everything you need to know about Bennington holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Bennington holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Bennington holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bennington holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bennington holiday rentals we have selected for you start as low as NZ$474 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Bennington rentals

At Expedia, we put the best Bennington holiday 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 holiday.

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. 

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?

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 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.