Bennington Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Bennington vacation rentals

Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (12 reviews)
"The best stay ever!!! Very clean, great location, super cozy, all the amenities you would need. 5/5 stars, we will be coming back :)"
United States
Carolina I.
The price is CA $124
CA $448 total
includes taxes & fees
May 12 - May 13
Cozy Bromley Retreat
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
7.8 out of 10, Good, (58 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is CA $97
CA $332 total
includes taxes & fees
May 12 - May 13
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Terrace/patio

Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (32 reviews)
"Great place!!"
United States
Margaret D.
The price is CA $127
CA $326 total
includes taxes & fees
May 12 - May 13
Peaceful getaway at birds of a feather
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
8.4 out of 10, Very good, (34 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.
The price is CA $97
CA $422 total
includes taxes & fees
May 12 - May 13
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Property grounds

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
7.4 out of 10, Good, (21 reviews)
"Poor management company. Great lodge. "
United States
Billy W.
The price is CA $182
CA $530 total
includes taxes & fees
May 12 - May 13
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
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, (31 reviews)
"Great location."
United States
Jeffrey
The price is CA $183
CA $499 total
includes taxes & fees
May 12 - May 13
Stratton Mtn Studio | Renovated | Walk to Lifts
Property grounds

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (61 reviews)
"This home was spacious, super clean, and in a great location. "
United States
Des C.
The price is CA $234
CA $332 total
includes taxes & fees
May 12 - May 13
Spacious apartment in beautiful, historic Arlington VT
Exterior

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
8.0 out of 10, Very good, (1 review)
"Great location and covered parking. "
United States
Jonathan M.
The price is CA $103
CA $295 total
includes taxes & fees
May 12 - May 13
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
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, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is CA $420
CA $522 total
includes taxes & fees
May 17 - May 18
Long Trail House at Stratton Mountain Resort
Smart TV

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is CA $159
CA $280 total
includes taxes & fees
May 12 - May 13
Cozy Home in Pownal VT
Dining

Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (1 review)
"This rental perfectly met our short term rental needs. Our two dogs enjoyed the spacious yard and we enjoyed the charms of an older home. Host was very flexible and responded timely to any inquiries. Would recommend."
United States
John Q.
The price is CA $148
CA $542 total
includes taxes & fees
May 12 - May 13
Historic Home with Colonial Charm in Manchester
Exterior

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, (25 reviews)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
United States
Chris M.
The price is CA $254
CA $1,167 total
includes taxes & fees
May 17 - May 18
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
TV, fireplace, books, music library

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (12 reviews)
"Comfortable accommodations, with responsive and helpful hosts! We had a lovely stay as a large family group for a wedding weekend in Manchester. "
United States
Colleen H.
The price is CA $246
CA $892 total
includes taxes & fees
May 12 - May 13
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Interior

Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT
Manchester
10.0 out of 10, Exceptional, (1 review)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
The price is CA $312
CA $771 total
includes taxes & fees
May 13 - May 14
Cozy 3 Bedroom Condo in the Heart of Manchester VT
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.
The price is CA $190
CA $442 total
includes taxes & fees
May 14 - May 15
Green Mountain Getaway
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (37 reviews)
"Our family had a wonderful time staying in this home."
United States
Meghan C.
The price is CA $270
CA $907 total
includes taxes & fees
May 12 - May 13
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Exterior detail

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (29 reviews)
"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."
United States
s w.
The price is CA $254
CA $1,185 total
includes taxes & fees
May 18 - May 19
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Private kitchen

Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
The price is CA $180
CA $584 total
includes taxes & fees
May 12 - May 13
Modern Mountain Retreat w/ Chef’s Kitchen
Terrace/patio

The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
Sunderland
10.0 out of 10, Exceptional, (4 reviews)
"Excellent host very responsive. Beautiful cozy cabin with all the amenities you need. Highly recommend! "
United States
Robert V.
The price is CA $285
CA $834 total
includes taxes & fees
May 19 - May 20
The Birchwood Cabin - Stunning Mountain Views
Living area

Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
The price is CA $222
CA $549 total
includes taxes & fees
May 12 - May 13
Long Trail House South Wing 2B2B Condo
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

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good
"Room was clean and comfortable and quiet. There was plenty of parking. Rooms were recently remodeled. There wasn't a lot to choose from for breakfast but it was adequate. The landline in our room didn't work so if you wanted the front desk, you had to walk there. (We asked but no one came to fix it or change the burned-out light in the sauna.) When we asked for extra pillows, there were none available. The sink in the bathroom is too close to the storage shelf over it so if you bend down to wash your face, your head can touch the shelf."
Jane 3-night trip
Posted 3 hours ago
Hotel Vervana, Trademark Collection by Wyndham

Find out more about Bennington

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Bennington. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Bennington?

Yes, we have vacation rentals in Bennington close to Bennington Center for the Arts, or you can select a more remote option if you'd like 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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: Visitors like this Bennington vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 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 selection of games and a hot tub.

How many vacation rentals will I find in Bennington?

With 12 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.