Holiday Homes in Bennington

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Holiday Homes in Bennington

Our top choices for Bennington holiday homes

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (256)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is AU$350
includes taxes & fees
16 Sept - 17 Sept
Berkshire Village Carriage House - Super Private!!
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (50)
"Great condo in great location. Easy walk to restaurants and lifts."
The price is AU$390
includes taxes & fees
24 Aug - 25 Aug
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Peaceful Stay at Birds of a Feather Farm & Spa
Interior

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (20)
"Great little quiet and peaceful spot that was still very close to Bennington and Manchester.Neighborhood was good for walks or gravel rides."
The price is AU$422
includes taxes & fees
24 Aug - 25 Aug
Peaceful Stay at Birds of a Feather Farm & Spa
The Mountain Escape!
Outdoor spa tub

The Mountain Escape!

9.8 out of 10, Exceptional, (18)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is AU$894
includes taxes & fees
1 Sept - 2 Sept
The Mountain Escape!
Cozy motel suite in charming Woodford with WiFi, AC
Interior

Cozy motel suite in charming Woodford with WiFi, AC

The price is AU$256
includes taxes & fees
6 Sept - 7 Sept
Cozy motel suite in charming Woodford with WiFi, AC
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

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

8.6 out of 10, Excellent, (32)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is AU$476
includes taxes & fees
24 Aug - 25 Aug
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Alpine 5, cozy Vermont retreat
1 bedroom, desk, iron/ironing board, WiFi

Alpine 5, cozy Vermont retreat

The price is AU$243
includes taxes & fees
24 Aug - 25 Aug
Alpine 5, cozy Vermont retreat
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub

Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

9.8 out of 10, Exceptional, (26)
"Amazing stay. Perfect weekend friend getaway"
The price is AU$894
includes taxes & fees
11 Sept - 12 Sept
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
Ski in Ski out Condo! Pool access
Terrace/patio

Ski in Ski out Condo! Pool access

9.0 out of 10, Wonderful, (2)
"Great location with plenty of space for the whole family. Highly recommend!"
The price is AU$839
includes taxes & fees
25 Aug - 26 Aug
Ski in Ski out Condo! Pool access
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
House, 3 Bedrooms | Exterior

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. "
The price is AU$1,000
includes taxes & fees
24 Aug - 25 Aug
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"This place was very enjoyable, it was just 3 of us so there was more than enough room. It is a very comfortable home and we enjoyed the easy trip into Manchester for some meals and a wonderful day of hiking some great nearby trails."
The price is AU$1,001
includes taxes & fees
2 Sept - 3 Sept
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Exterior

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

10.0 out of 10, Exceptional, (4)
"Great location, large space for family, good amenities, love the fireplace and coffee set up."
The price is AU$1,141
includes taxes & fees
27 Aug - 28 Aug
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Two Brooks Lodge
Panoramic House | Private kitchen

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...
Two Brooks Lodge
Vermont Getaway near Stratton Mountain
Fridge, microwave, oven, stovetop

Vermont Getaway near Stratton Mountain

9.0 out of 10, Wonderful, (11)
"The owner was quick to respond and more than accommodating on short notice. Would definitely come back. "
The price is AU$908
includes taxes & fees
14 Sept - 15 Sept
Vermont Getaway near Stratton Mountain
Tranquil farmhouse in Manchester - perfect for ski or summer fun!
Property grounds

Tranquil farmhouse in Manchester - perfect for ski or summer fun!

The price is AU$1,089
includes taxes & fees
28 Aug - 29 Aug
Tranquil farmhouse in Manchester - perfect for ski or summer fun!
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
4 bedrooms, iron/ironing board, WiFi, bed sheets

Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.

2.0 star property
10.0 out of 10, Exceptional, (7)
"Awesome."
The price is AU$2,247
includes taxes & fees
26 Aug - 27 Aug
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
Room 7 - family room sleeps 4
Property grounds

Room 7 - family room sleeps 4

Room 7 - family room sleeps 4
Zen 10, relax and retreat in the heart of Vermont
Property grounds

Zen 10, relax and retreat in the heart of Vermont

The price is AU$243
includes taxes & fees
24 Aug - 25 Aug
Zen 10, relax and retreat in the heart of Vermont
Cozy 4-bedroom condo with AC, WiFi in charming Stratton
Exterior

Cozy 4-bedroom condo with AC, WiFi in charming Stratton

The price is AU$1,854
includes taxes & fees
4 Sept - 5 Sept
Cozy 4-bedroom condo with AC, WiFi in charming Stratton
Room 4 - Prickly Pear double room
1 bedroom, desk, iron/ironing board, travel cot

Room 4 - Prickly Pear double room

Room 4 - Prickly Pear double room
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.
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

The Four Chimneys Inn

The Four Chimneys Inn

10/10 Excellent
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite. "
Jon 1-night trip
Posted 2 days ago
The Four Chimneys Inn