Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Bennington vacation rentals

Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (10 reviews)
"As always, an excellent stay. Wonderful unit, very nicely stocked in a perfect location. Communication was quick and easy. Easily my favorite place to stay!"
United States
Vanessa P.
$313 nightly
The price is $353
Feb 1 - Feb 2
Total with taxes and fees
Cozy Bromley Retreat
Terrace/patio

Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa
Shaftsbury
9.8 out of 10, Exceptional, (30 reviews)
"Great place!!"
United States
Margaret D.
$220 nightly
The price is $246
Feb 1 - Feb 2
Total with taxes and fees
Peaceful Stay at Birds of a Feather Farm & Spa
Outdoor spa tub

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, (82 reviews)
"Nice place and great location!!!"
United States
William
$460 nightly
The price is $520
Mar 1 - Mar 2
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
Dining

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
$178 nightly
The price is $200
Feb 1 - Feb 2
Total with taxes and fees
Cozy Home in Pownal VT
Property grounds

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, (28 reviews)
"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.
$359 nightly
The price is $406
Feb 4 - Feb 5
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Exterior

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 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.
$258 nightly
The price is $274
Feb 4 - Feb 5
Total with taxes and fees
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Smart TV, fireplace, books, computer monitors

6 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.

6 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.
Winhall
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful location close to ski resorts and towns. Well maintained property with all the amenities of home. Had a wonderful time staying here! "
United States
Caroline F.
$381 nightly
The price is $430
Feb 5 - Feb 6
Total with taxes and fees
6 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.
House, 4 Bedrooms | View from property

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
Arlington
8.0 out of 10, Very Good, (1 review)
"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
$621 nightly
The price is $686
Feb 11 - Feb 12
Total with taxes and fees
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Property grounds

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (59 reviews)
"This home was spacious, super clean, and in a great location. "
United States
Des C.
$216 nightly
The price is $242
Feb 1 - Feb 2
Total with taxes and fees
Spacious apartment in beautiful, historic Arlington VT
Smart TV, fireplace

Luxury Condo Stratton Mountain

Luxury Condo Stratton Mountain
Stratton
10.0 out of 10, Exceptional, (1 review)
"Katherine was a perfect host. The house is beautiful and had everything we needed for our family vacation. Thank you so much! "
United States
Katryn B.
$2,567 nightly
The price is $2,602
Feb 3 - Feb 4
Total with taxes and fees
Luxury Condo Stratton Mountain
Pool

Equinox Getaway | Queen Room + Culinary Delights

Equinox Getaway | Queen Room + Culinary Delights
Manchester Village Historic District
$192 nightly
The price is $212
Feb 1 - Feb 2
Total with taxes and fees
Equinox Getaway | Queen Room + Culinary Delights
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
Stratton
7.6 out of 10, Good, (54 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
$314 nightly
The price is $355
Feb 11 - Feb 12
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Property grounds

Green Mountain Manor - Ski and Summer Chalet

Green Mountain Manor - Ski and Summer Chalet
Winhall
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"
United States
Jay T.
$4,488 nightly
The price is $5,071
Feb 21 - Feb 22
Total with taxes and fees
Green Mountain Manor - Ski and Summer Chalet
Exterior

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
$242 nightly
The price is $253
Feb 4 - Feb 5
Total with taxes and fees
Two Brooks Lodge
Living area

Green Mountain Getaway

Green Mountain Getaway
Bennington
9.6 out of 10, Exceptional, (18 reviews)
"Very clean property. The location was very convenient to the Main Street of Bennington. Easy check in process. Would definitely stay here again! "
United States
Meredith Y.
$381 nightly
The price is $407
Feb 3 - Feb 4
Total with taxes and fees
Green Mountain Getaway
Private kitchen

Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
$426 nightly
The price is $482
Feb 3 - Feb 4
Total with taxes and fees
Modern Mountain Retreat w/ Chef’s Kitchen
Exterior

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Manchester Center
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time."
United States
Neetesh B.
$1,840 nightly
The price is $2,079
Feb 9 - Feb 10
Total with taxes and fees
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Terrace/patio

The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
Sunderland
10.0 out of 10, Exceptional, (2 reviews)
"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.
$761 nightly
The price is $852
Feb 23 - Feb 24
Total with taxes and fees
The Birchwood Cabin - Stunning Mountain Views
Fridge, microwave, oven, stovetop

Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mtn Studio | Renovated | Walk to Lifts
Stratton Mountain
10.0 out of 10, Exceptional, (30 reviews)
"Great location."
United States
Jeffrey
$470 nightly
The price is $531
Feb 1 - Feb 2
Total with taxes and fees
Stratton Mtn Studio | Renovated | Walk to Lifts
Dining

Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
$484 nightly
The price is $546
Feb 24 - Feb 25
Total with taxes and fees
Historic Home with Colonial Charm in Manchester
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
"Room was great - no huge fee for pet"
Stacey 1-night trip
Posted 5 days ago
Hampton Inn Bennington

Price trends for vacation rentals in Bennington

Less expensive
More expensive
Next month
December
March
$343
Month
Price
January
$303
February
$343
March
$451
April
$310
May
$397
June
$442
July
$332
August
$314
September
$442
October
$322
November
$312
December
$289
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Bennington. Select dates and complete search for nightly totals inclusive of taxes and fees.

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 $274 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?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: Visitors like this Bennington vacation home rental. It is located on a river and has an outdoor pool, a fireplace, and a barbecue grill 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. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Bennington?

With 14 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, Bennington Battle Monument and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display 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.