Bennington Vacation Rentals

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Vacation Rentals in Bennington

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
8.6 out of 10, Excellent, (76)
"Nice, clean room in prime location"
United States
Kristin
$350 nightly
The price is $396
Nov 9 - Nov 10
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
Fridge, microwave, oven, stovetop
Cozy Bromley Retreat
Cozy Bromley Retreat
9.8 out of 10, Exceptional, (7)
"There is no place I’d rather stay in VT. It’s a perfect condo and the recent renovations are really nice. It’s got all the comforts of home and great touches throughout. Bromley is a great community to be in, it’s close to town, obviously the slopes, and just a overall stay!"
United States
Vanessa P.
$288 nightly
The price is $325
Nov 4 - Nov 5
Total with taxes and fees
Cozy Bromley Retreat
Microwave, coffee/tea maker, cookware/dishes/utensils, spices
Mountain Dream Escape
Mountain Dream Escape
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful location and home! The apartment was beautifully decorated and so cozy. The hot tub was a great place for stargazing! It was wonderful for our anniversary weekend but would also be great for a longer stay.Great communication with hosts and they were super helpful when we had a minor issue with check in."
United States
Morgan C.
$402 nightly
The price is $450
Nov 4 - Nov 5
Total with taxes and fees
Mountain Dream Escape
Outdoor dining
Green Mountain Getaway
Green Mountain Getaway
2.0 star property
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.
$401 nightly
The price is $427
Nov 4 - Nov 5
Total with taxes and fees
Green Mountain Getaway
Indoor pool, a heated pool
Equinox Haven | King Room + Culinary Delights
Equinox Haven | King Room + Culinary Delights
8.0 out of 10, Very Good, (1)
"Clean room. There was a trip hazard from bedroom to bathroom. Servers in restaurant were very attentive, courteous and professional. Food adequate but over priced."
United States
Anne Marie
$212 nightly
The price is $234
Nov 5 - Nov 6
Total with taxes and fees
Equinox Haven | King Room + Culinary Delights
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
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.
$254 nightly
The price is $269
Nov 4 - Nov 5
Total with taxes and fees
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Panoramic House | Private kitchen
Two Brooks Lodge
Two Brooks Lodge
3.0 star property
4.8 out of 10, (3)
"Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in the unit, had to go to hospital. We moved out after only 3 hours, and literally slept in the car rather than go back. Owner uncaring, rude and greedy. Slow to return security deposit. I've...
United States
John
$225 nightly
The price is $234
Nov 4 - Nov 5
Total with taxes and fees
Two Brooks Lodge
Interior
Peaceful Stay at Birds of a Feather Farm & Spa
Peaceful Stay at Birds of a Feather Farm & Spa
9.8 out of 10, Exceptional, (27)
"We absolutely loved this stay. The space was gorgeous and cozy. Fully equipped kitchen we were able to cook dinner in. The location about 45 minutes from Stratton where we skied, but was well worth the drive. Would absolutely stay here again. Thanks again Laurie! "
United States
Cassidy L.
$219 nightly
The price is $245
Nov 4 - Nov 5
Total with taxes and fees
Peaceful Stay at Birds of a Feather Farm & Spa
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
8.4 out of 10, Very Good, (26)
"Great location close to lift. Condo is clean and well appointed."
United States
Grace Ann B.
$246 nightly
The price is $278
Nov 9 - Nov 10
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
House, 3 Bedrooms | Exterior
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
8.0 out of 10, Very Good, (1)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
United States
Manish
$586 nightly
The price is $644
Nov 11 - Nov 12
Total with taxes and fees
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Interior
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
7.8 out of 10, Good, (52)
"Clean and convenient location to the village and base."
United States
Adam C.
$220 nightly
The price is $249
Nov 4 - Nov 5
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior
Stratton Mtn Studio | Renovated | Walk to Lifts
Stratton Mtn Studio | Renovated | Walk to Lifts
10.0 out of 10, Exceptional, (30)
"Great location."
United States
Jeffrey
$374 nightly
The price is $423
Nov 4 - Nov 5
Total with taxes and fees
Stratton Mtn Studio | Renovated | Walk to Lifts
Property grounds
Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!
Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!
$409 nightly
The price is $458
Nov 5 - Nov 6
Total with taxes and fees
Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!
Fridge, microwave, oven, stovetop
New! Vermont Getaway! Stratton - close to skiing!
New! Vermont Getaway! Stratton - close to skiing!
2.0 star property
$454 nightly
The price is $461
Nov 4 - Nov 5
Total with taxes and fees
New! Vermont Getaway! Stratton - close to skiing!
Private kitchen
The Birchwood Cabin - Stunning Mountain Views
The Birchwood Cabin - Stunning Mountain Views
2.0 star property
10.0 out of 10, Exceptional, (2)
"This cabin was everything we could have asked for! Great, peaceful location with a beautiful view. Tastefully decorated and wonderful open concept for kitchen and living room set-up. We really enjoyed the game room downstairs, too. We will definitely be back soon."
United States
Shannon C.
$609 nightly
The price is $682
Nov 18 - Nov 19
Total with taxes and fees
The Birchwood Cabin - Stunning Mountain Views
Property grounds
Spacious apartment in beautiful, historic Arlington VT
Spacious apartment in beautiful, historic Arlington VT
10.0 out of 10, Exceptional, (57)
"Perfect place to stay outside Manchester. The place is so spacious and quiet! Extremely responsive and friendly. "
United States
Grace M.
$195 nightly
The price is $218
Nov 4 - Nov 5
Total with taxes and fees
Spacious apartment in beautiful, historic Arlington VT
4 bedrooms, iron/ironing board, WiFi, bed sheets
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
2.0 star property
10.0 out of 10, Exceptional, (7)
"Our family ski vacation was awesome at this gorgeous mountain home which is only 2 minutes from Stratton mountain. Beautiful decor, hot tub, fireplace, and fun family games to play. Kitchen has everything you need and more. Book it now you won’t be disappointed! "
United States
Stacie P.
$1,505 nightly
The price is $1,701
Nov 24 - Nov 25
Total with taxes and fees
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
Indoor pool
Luxurious Escape + Pool & Hot Tub Access
Luxurious Escape + Pool & Hot Tub Access
$772 nightly
The price is $851
Nov 30 - Dec 1
Total with taxes and fees
Luxurious Escape + Pool & Hot Tub Access
Exterior
Bear Pass - Mountain View by RedAwning
Bear Pass - Mountain View by RedAwning
9.6 out of 10, Exceptional, (5)
"We had a great stay at Bear Pass. The size of the house was perfect for our family. The kitchen was fully stocked with anything you might need. There was plenty of sleeping options, with 3 bedrooms and a fully furnished basement with 2 twin beds and a sitting area with a couch, and a bathroom. The property is large and would be very nice to enjoy in the warmer months. The house is located near several mountains that made for great skiing. We went to Bromley and it was about a 20-25 min drive....
United States
Betsy S.
$602 nightly
The price is $675
Nov 4 - Nov 5
Total with taxes and fees
Bear Pass - Mountain View by RedAwning
Dining
Bromley Aframe - King Master Bed, Wood Fireplace
Bromley Aframe - King Master Bed, Wood Fireplace
9.6 out of 10, Exceptional, (14)
"This house was great for my family's spring vacation. The stream was beautiful and relaxing. "
United States
Loni N.
$396 nightly
The price is $443
Nov 30 - Dec 1
Total with taxes and fees
Bromley Aframe - King Master Bed, Wood Fireplace
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
"The breakfast was exceptional there was a lot of options to choose from the rooms are very clean we enjoyed our stay"
Richard 1-night trip
Posted 4 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 $269 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?

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 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.