Bennington Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Jan - 14 Jan
Tomorrow
14 Jan - 15 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Bennington holiday rentals

Children’s area
Cozy Bromley Retreat

Apartment in Bromley Mountain

Cozy Bromley Retreat
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.
The price is HK$787
HK$2,639 total
includes taxes & fees
15 Jan - 16 Jan
Cozy Bromley Retreat
Terrace/patio
Peaceful Stay at Birds of a Feather Farm & Spa

Holiday Home in Shaftsbury

Peaceful Stay at Birds of a Feather Farm & Spa
9.8 out of 10, Exceptional, (30 reviews)
"Great place!!"
United States
Margaret D.
The price is HK$772
HK$1,912 total
includes taxes & fees
15 Jan - 16 Jan
Peaceful Stay at Birds of a Feather Farm & Spa
Outdoor spa tub
Long Trail House at Stratton Mountain Resort

Aparthotel in Stratton

Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (78 reviews)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is HK$2,968
HK$3,690 total
includes taxes & fees
19 Jan - 20 Jan
Long Trail House at Stratton Mountain Resort
Exterior
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Holiday Home in Bennington

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
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.
The price is HK$865
HK$2,215 total
includes taxes & fees
15 Jan - 16 Jan
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Living area
Green Mountain Getaway

Apartment in Bennington

Green Mountain Getaway
2.0 star property
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 HK$1,205
HK$2,645 total
includes taxes & fees
15 Jan - 16 Jan
Green Mountain Getaway
Exterior detail
Charming Dorset Cottage Retreat.

Holiday Home in Dorset

Charming Dorset Cottage Retreat.
2.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay at this beautiful, cozy cottage in Dorset. It’s close to multiple ski mountains and the charming town of Manchester, and the hosts were super friendly and helpful. Check-in and check-out were easy, and the place was just as advertised."
United States
Sarah S.
The price is HK$2,705
HK$6,209 total
includes taxes & fees
21 Jan - 22 Jan
Charming Dorset Cottage Retreat.
Property grounds
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Condo in Stratton

Lovely ski-in/out condo steps from ski lift with trails and amazing views
8.6 out of 10, Excellent, (27 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 HK$1,107
HK$3,413 total
includes taxes & fees
15 Jan - 16 Jan
Lovely ski-in/out condo steps from ski lift with trails and amazing views
View from property
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Holiday Home in Arlington

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
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
The price is HK$1,907
HK$5,264 total
includes taxes & fees
25 Jan - 26 Jan
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Property grounds
Spacious apartment in beautiful, historic Arlington VT

Apartment in Arlington

Spacious apartment in beautiful, historic Arlington VT
10.0 out of 10, Exceptional, (59 reviews)
"Great place—though it’s a basement, it’s nearly perfect. We’d definitely stay here again"
United States
aytac
The price is HK$1,333
HK$1,886 total
includes taxes & fees
15 Jan - 16 Jan
Spacious apartment in beautiful, historic Arlington VT
Fridge, microwave, oven, stovetop
Stratton Mtn Studio | Renovated | Walk to Lifts

Condo in Stratton Mountain

Stratton Mtn Studio | Renovated | Walk to Lifts
10.0 out of 10, Exceptional, (30 reviews)
"Great location."
United States
Jeffrey
The price is HK$2,144
HK$4,202 total
includes taxes & fees
19 Jan - 20 Jan
Stratton Mtn Studio | Renovated | Walk to Lifts
Interior
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Holiday Home in Stratton

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
7.8 out of 10, Good, (52 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is HK$1,162
HK$3,108 total
includes taxes & fees
22 Jan - 23 Jan
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Exterior
The Vermont A-Frame Mountain Retreat

Cabin in Winhall

The Vermont A-Frame Mountain Retreat
9.8 out of 10, Exceptional, (26 reviews)
"This was the perfect cabin to set up base for exploring the area on my New England road trip. Its vintage charm with modern upgrades set the mood perfectly to kick off October! It’s slightly off the main road, but the cabin is tucked away enough that I didn’t even notice. Great location for the local tourist attractions!"
United States
AmyC
The price is HK$1,777
HK$4,056 total
includes taxes & fees
22 Jan - 23 Jan
The Vermont A-Frame Mountain Retreat
Terrace/patio
The Birchwood Cabin - Stunning Mountain Views

Cabin in Sunderland

The Birchwood Cabin - Stunning Mountain Views
2.0 star property
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.
The price is HK$3,014
HK$6,467 total
includes taxes & fees
28 Jan - 29 Jan
The Birchwood Cabin - Stunning Mountain Views
Property grounds
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Condo in Stratton

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
7.4 out of 10, Good, (20 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is HK$1,146
HK$3,393 total
includes taxes & fees
15 Jan - 16 Jan
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Indoor pool, a heated pool
Equinox Haven | King Room + Culinary Delights

Apartment in Manchester Village Historic District

Equinox Haven | King Room + Culinary Delights
8.0 out of 10, Very good, (1 review)
"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
The price is HK$1,847
HK$2,322 total
includes taxes & fees
20 Jan - 21 Jan
Equinox Haven | King Room + Culinary Delights
Interior
Bear Pass - Mountain View by RedAwning

Holiday Home in Sunderland

Bear Pass - Mountain View by RedAwning
9.6 out of 10, Exceptional, (5 reviews)
"We loved our stay at Bear Pass! The kitchen was more than adequately stocked. The hous was great for our extended family and our 3 dogs"
United States
Megan G.
The price is HK$1,961
HK$5,056 total
includes taxes & fees
15 Jan - 16 Jan
Bear Pass - Mountain View by RedAwning
Exterior
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

Holiday Home in Manchester Center

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time."
United States
Neetesh B.
The price is HK$7,557
HK$16,293 total
includes taxes & fees
21 Jan - 22 Jan
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Exterior
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Holiday Home in Jamaica

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
9.6 out of 10, Exceptional, (23 reviews)
"Absolutely a wonderful place to vacation. The house is comfortable and warming. The hosts went above and beyond to make our stay great and responded to our questions promptly. We will definitely rent again. "
United States
Lee Anna C.
The price is HK$3,017
HK$8,069 total
includes taxes & fees
19 Jan - 20 Jan
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Smart TV, fireplace
Luxury Condo Stratton Mountain

Holiday Home in Stratton

Luxury Condo Stratton Mountain
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.
The price is HK$9,356
HK$13,307 total
includes taxes & fees
20 Jan - 21 Jan
Luxury Condo Stratton Mountain
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington Hotel Reviews

Harwood Hill Motel

Harwood Hill Motel

10/10 Excellent
"Spotless, clean and friendly!"
Tobias 1-night trip
Posted 7 days ago
Harwood Hill Motel

Find out more about Bennington

Search for holiday rentals in Bennington on Expedia! You can easily find your home rentals, villas, holiday apartments in Bennington using one of the methods below:

  • View our selection of featured holiday rentals in Bennington
  • Use the map to find apartments and other holiday homes in the Bennington neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Bennington while they last

Look no further and take a look at our great range of rental properties in Bennington!

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?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Bennington is located on a river, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Bennington?

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