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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 26 Chalets in Bennington with updated reviews, rates, and availability.

Classic Alpine Vermont Chalet
Fridge, microwave, oven, stovetop

Classic Alpine Vermont Chalet

10.0 out of 10, Exceptional, (10)
"The house was just what we needed for a family wedding in Manchester. Quite literally right off the highway but the house itself is nestled back and quiet so you don’t even hear the road. "
Classic Alpine Vermont Chalet
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

9.4 out of 10, Exceptional, (6)
"We were absolutely thrilled to experience a fresh powder drop during our stay, which was a delightful surprise in an otherwise dry season. The house surpassed all our expectations, providing the perfect haven for our large group. It was impeccably clean, incredibly warm, and featured an abundance of comfortable beds, all while being conveniently close to the mountain. A standout feature for us was the Tesla charger in the garage, which met our specific needs perfectly. We are already eagerly...
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
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, (32)
"We had 9 people in 2 family units staying at house. Then about another 6 that came each night to hang out. Plenty of room. 3 living room areas for everyone to spread out. Best stocked home EVER!!! There was literally everything and anything that we needed…..and then some. Inside sauna so cool. Unfortunately way too cold to go out and enjoy the hot tub. Decorations beyond beautiful. Owner very quick with communication. Highly recommend staying here. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub
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
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)
"Overall, a very good stay. The house is a bit smaller than we thought, but it was very clean and well stocked. The indoor fireplace and provided wood was a nice perk. The hot tub was not clean or well kept, so beware of that. There were body hairs and a brown scum ring around the edge."
Stylish Mountain Getaway close to Stratton w/ Spa
Green Mountain Manor - Ski and Summer Chalet
Property grounds

Green Mountain Manor - Ski and Summer Chalet

9.8 out of 10, Exceptional, (7)
"Relaxing VT stay . You are in a rural setting but places to stock up on supplies was less then 10 miniutes away . We watched the fireworks that stratton displayed pretty much from the comfort of the property .Our children are young adults and they had a blast finding local swimholes . As well as spending a day at Bromley Mountain ( 20 mins away ) where they did water slides , alpine slides , the giant swing to name a few . House is large and the ability to accomodate large families or groups ....
Green Mountain Manor - Ski and Summer Chalet
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
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
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 fantastic stay at this rental! The home was spotless and well-maintained, making it a comfortable and relaxing getaway. It’s conveniently located in the Stratton Mountain area and just a 20-minute drive from Bromley Mountain, making it a great spot for skiing and winter activities.Our kids loved playing in the snow and especially enjoyed the hot tub after a day outside. The kitchen was fully stocked with everything we needed, making meal prep easy. One of the highlights was the real...
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
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

10.0 out of 10, Exceptional, (13)
"This house was a great spot for 6 adults (parents & grandparents) and 4 kids (7-10 yrs). The upstairs living space worked very well and the kids enjoyed their space downstairs with the Pac-Man game and pool table. Location made it easy to get to the slopes. We had a terrific time and would love to return."
The price is SAR 1,178
SAR 2,696 total
includes taxes & fees
21 Apr - 22 Apr
Ski Haus @ Quartermile 3 mins from Base / shuttle King Beds with Private Baths
Serene & Stylish Chalet w/ HOT TUB near Manchester and Skiing
Outdoor spa tub

Serene & Stylish Chalet w/ HOT TUB near Manchester and Skiing

10.0 out of 10, Exceptional, (13)
"It's a great area, we had so much fun, a beautiful house, and a very nice host. "
Serene & Stylish Chalet w/ HOT TUB near Manchester and Skiing
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)
"The only problem I had was with the heat Issue with check in but was resolved in satisfactory time "
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton
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
Bromley Aframe - King Master Bed, Wood Fireplace
Dining

Bromley Aframe - King Master Bed, Wood Fireplace

9.8 out of 10, Exceptional, (12)
"The property and house are truly beautiful. Great for a family stay. Fall foliage views are beautiful. The owner responded to all of my messages in a timely fashion. Located only two minutes away from Bromley which was great. There was a ceiling leak in the hallway while we were there but it wasn't bad. It was just the two of staying for one night and I do feel that charging the full cleaning fee for the one night for just the two of us was a bit high/overpriced. It would be nice if it could...
Bromley Aframe - King Master Bed, Wood Fireplace
Wellness Spa | Barrel Sauna & Hot Tub
Smart TV, fireplace, books, computer monitors

Wellness Spa | Barrel Sauna & Hot Tub

10.0 out of 10, Exceptional, (3)
"Fantastic location, scenery and chalet. Everything was amazing. Our hosts were attentive friendly and welcoming. We really appreciate that, especially now when customer service seems to be declining. "
Wellness Spa | Barrel Sauna & Hot Tub
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)
"Property was well equipped and super clean. Tom was incredibly accommodating. There was a snow storm, but he cleared the snow for us, so we got first tracks! House was nicely updated and comfortable. "
Perfect house surrounded by National Forest to get away and decompress!!!
10 min from Stratton! Log Cabin w/ Beautiful Views
Interior

10 min from Stratton! Log Cabin w/ Beautiful Views

10.0 out of 10, Exceptional, (10)
"Great cabin with ample accommodations and accoutrements! Nice record collection and peaceful quiet when needed. "
10 min from Stratton! Log Cabin w/ Beautiful Views
Mountain chalet close to Manchester Center
Exterior

Mountain chalet close to Manchester Center

Mountain chalet close to Manchester Center
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
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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Other property types in Bennington

Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

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

8.8 out of 10, Excellent, (28)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is SAR 356
SAR 982 total
includes taxes & fees
22 Apr - 23 Apr
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Victorian Home in Bennington, Vermont
Fridge, microwave, oven, stovetop

Victorian Home in Bennington, Vermont

10.0 out of 10, Exceptional, (88)
"This is a wonderful property. Very spacious and nicely decorated. Master bathroom is huge with lots of thick fluffy towels. The hosts did a wonderful job making us feel welcome with lots of treats waiting for us when we checked in- bottled waters (sparking and plain) crackers and cheese, peanuts, coffee, half n half. This was a. Ice touch and very appreciated. It’s a very short walk into town with lots of restaurants and breweries Rally great place - would definitely stay here again!"
Victorian Home in Bennington, Vermont
Historic Downtown Home w/Bar Room, Hot Tub
Interior

Historic Downtown Home w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (12)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Historic Downtown Home w/Bar Room, Hot Tub
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.