Chalets in Bennington County

Compare and save

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Top Cities in Bennington County

Bennington Battle Monument showing landscape views
ChaletsChalets

Bennington

Bennington

Compare 24 Chalets in Bennington County with updated reviews, rates, and availability.

Mid-Century Arty Chalet - 2 Min to Stratton Slopes
Smart TV, fireplace, computer monitors

Mid-Century Arty Chalet - 2 Min to Stratton Slopes

8.8 out of 10, Excellent, (3)
"The house is in a great location for skiing at Stratton! 5 mins drive to the base or shuttle service running every 30 mins. Perfect for a cozy ski weekend with the fireplace. We enjoyed it very much! "
Mid-Century Arty Chalet - 2 Min to Stratton Slopes
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Exterior

Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

10.0 out of 10, Exceptional, (50)
"We enjoyed skylight lodge. We get together with family and friends each year to do an annual fundraising event. The house was perfect for our group. The big fireplace was a great way to relax after a day of skiing or snowshoeing. "
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
Fridge, microwave, oven, stovetop

Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck

9.2 out of 10, Wonderful, (7)
"Nice hill for sledding. Missed having electric mixer for potatoes. Nice community area of kitchen, dining room and living room. Good setup of rooms. "
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
Stylish Mountain Getaway close to Stratton w/ Spa
Aerial view

Stylish Mountain Getaway close to Stratton w/ Spa

9.8 out of 10, Exceptional, (7)
"Amazing! Host was readily available to handle any questions and the house was very comfortable and relaxing. "
Stylish Mountain Getaway close to Stratton w/ Spa
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Fridge, microwave, oven, stovetop

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (34)
"Stayed 3 nights everything was spotless & so very comfortable. This was our 2nd stay here. The host is always reachable & prompt to respond. Can’t wait to hopefully stay here again. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Brian Piece of Heaven for fall Foliage. Beautiful colors
Fridge, microwave, oven, stovetop

Brian Piece of Heaven for fall Foliage. Beautiful colors

9.8 out of 10, Exceptional, (30)
"Perfect spot to getaway for a weekend trip"
Brian Piece of Heaven for fall Foliage. Beautiful colors
Green Mountain Manor - Ski and Summer Chalet
Property grounds

Green Mountain Manor - Ski and Summer Chalet

9.8 out of 10, Exceptional, (7)
"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"
Green Mountain Manor - Ski and Summer Chalet
Classic Stratton Ski Chalet: Perfect for Families
Terrace/patio

Classic Stratton Ski Chalet: Perfect for Families

10.0 out of 10, Exceptional, (1)
"Enjoyed our three night stay here. The kitchen is well stocked with pots and pans, dinnerware, silverware, utensils, etc. Beds were very comfortable. Our only disappointment was that we couldn't have a fire in the fireplace as the chimney was in need of repairs. Hope to be back next year."
Classic Stratton Ski Chalet: Perfect for Families
Classic Alpine Vermont Chalet
Fridge, microwave, oven, stovetop

Classic Alpine Vermont Chalet

10.0 out of 10, Exceptional, (10)
"Easiest vrbo experience we’ve had to date."
Classic Alpine Vermont Chalet
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
Smart TV, fireplace, video games

Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!

10.0 out of 10, Exceptional, (10)
"We had a wonderful time and enjoyed our stay at your home! Great space and the kids loved playing downstairs and sleeping in the bunk room!"
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton
Fridge, microwave, oven, stovetop

4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton

9.0 out of 10, Wonderful, (20)
"Gorgeous rental and the hot tub was great, perfect for a big group."
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton
Serene & Stylish Chalet ~HOT TUB ~ near Manchester ~ Pet-friendly
Outdoor spa tub

Serene & Stylish Chalet ~HOT TUB ~ near Manchester ~ Pet-friendly

10.0 out of 10, Exceptional, (13)
"Cozy and warm. It was a nice get away for me and my girlfriend I would visit again. "
Serene & Stylish Chalet ~HOT TUB ~ near Manchester ~ Pet-friendly
Ski Haus @ Quartermile 3 mins from Base / shuttle King Beds with Private Baths
Smart TV, fireplace, video games, stereo

Ski Haus @ Quartermile 3 mins from Base / shuttle King Beds with Private Baths

9.8 out of 10, Exceptional, (15)
"Great location on the shuttle route. The house is very nice with lots of amenities. Highly recommended."
Ski Haus @ Quartermile 3 mins from Base / shuttle King Beds with Private Baths
Charming 5BR Chalet@Base of Stratton Mt Has It All
Exterior

Charming 5BR Chalet@Base of Stratton Mt Has It All

9.2 out of 10, Wonderful, (12)
"Our trip this past weekend to Chalet O'Bear was just what we wanted! Booking and communication with the property manager was seamless. Any issues we had were addressed immediately and taken care of. We loved the location of the property and made our stay at Stratton perfect! We will be looking to book again! "
Charming 5BR Chalet@Base of Stratton Mt Has It All
Bromley Aframe - King Master Bed, Wood Fireplace
Dining

Bromley Aframe - King Master Bed, Wood Fireplace

9.8 out of 10, Exceptional, (13)
"Visited for the fall foliage, and Vermonr is absolutely stunning. Bromely house was clean, comfortable and was as advertised. Location was perfect for our stay. Would not hesitate to stay there again."
Bromley Aframe - King Master Bed, Wood Fireplace
Perfect house surrounded by National Forest to get away and decompress!!!
Fridge, microwave, oven, stovetop

Perfect house surrounded by National Forest to get away and decompress!!!

10.0 out of 10, Exceptional, (3)
"This house was the perfect vacation spot. Clean, well appointed, and with a very accessible owner. No complaints here! Will be back. "
Perfect house surrounded by National Forest to get away and decompress!!!
Wellness Spa | 5 Min to Swimming Pond
Smart TV, fireplace, books, computer monitors

Wellness Spa | 5 Min to Swimming Pond

10.0 out of 10, Exceptional, (3)
"We had an awesome stay. So much to do in the area. Accommodations were spotless and communication was great. Loved it. "
Wellness Spa | 5 Min to Swimming Pond
Paradise Vermont, Nature Chalet With Indoor Hot Tub
Interior

Paradise Vermont, Nature Chalet With Indoor Hot Tub

Paradise Vermont, Nature Chalet With Indoor Hot Tub
Cozy Ski Chalet close to Stratton sleeps 10
Exterior

Cozy Ski Chalet close to Stratton sleeps 10

10.0 out of 10, Exceptional, (2)
"This is a great updated property on a wooded lot with plenty of privacy. Great secluded feeling but a short drive to Manchester, Stratton, and other VT attractions. Highly recommend a stay here."
Cozy Ski Chalet close to Stratton sleeps 10
Mountain chalet close to Manchester Center
Exterior

Mountain chalet close to Manchester Center

Mountain chalet close to Manchester Center
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