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Compare 20 Chalets in Bennington with updated reviews, rates, and availability.

Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Welcome to Skylight Ski Lodge!

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

10.0 out of 10, Exceptional, (48)
"My family and I had a great stay at the Skylight Lodge. It is very different from other rentals, being a former inn. There is plenty of space for a big group and the two master suites are great. The fireplace in the main room is like something out of game of thrones, and was the highlight of the trip for the adults. The kids spent most of the time playing games in the second living room on the first floor. The house is also very conveniently located near Manchester. We would definitely come...
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Aerial view

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (30)
"The house was very cozy and easy to get comfortable. It is surrounded by woods. We were lucky to get a lot of snow one day of our stay so we were literally in a magnificent winter wonderland-a perfect stay!"
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Serene & Stylish Chalet w/ HOT TUB near Manchester
Kick back and enjoy the large Living & Dining Great Room with high ceilings

Serene & Stylish Chalet w/ HOT TUB near Manchester

10.0 out of 10, Exceptional, (12)
"Cozy and warm. It was a nice get away for me and my girlfriend I would visit again. "
Serene & Stylish Chalet w/ HOT TUB near Manchester
Charming 5BR Chalet@Base of Stratton Mt Has It All
Great Rm Living Rm3

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

9.6 out of 10, Exceptional, (9)
"This property is absolutely perfect for a large group staying at Stratton. Plenty of bedrooms / beds / baths, open space around the kitchen and living room areas, plenty of parking and more. Fireplace is great. Hot tub and sauna come in clutch. Location is ideal. Owner communicates great. We were a group of 9 friends up for a quick ski trip. Would definitely book it again."
Charming 5BR Chalet@Base of Stratton Mt Has It All
Stylish Mountain Getaway close to Stratton w/ Spa
Spacious living room

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
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Open Living room

Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

9.6 out of 10, Exceptional, (45)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Green Mountain Manor - Ski and Summer Chalet
Aerial view

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

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
Brian Piece of Heaven for fall Foliage. Beautiful colors
Exterior

Brian Piece of Heaven for fall Foliage. Beautiful colors

9.8 out of 10, Exceptional, (29)
"The place was adorable , very clean , view was pretty and Brian the host was very friendly and accommodating. Loved it!"
Brian Piece of Heaven for fall Foliage. Beautiful colors
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton
Updated and fully stocked kitchen

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

9.2 out of 10, Wonderful, (19)
"As a yearly VRBO renter I am accustom to renting a few houses and this one had some disappointing takes and some great attributes. First the houses layout and location is great for a large get together and the views are amazing! But apon arriving you could first tell the slate entry way and door knob was in need of repair. From there we had a few other dissapointments, the dishes were dirty, scattered about the kitchen. Towels were damp and we later learned why, it was because the dryer simply...
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton
On Shuttle, 12 min walk to village. King Beds with Private Baths
Exterior

On Shuttle, 12 min walk to village. King Beds with Private Baths

9.8 out of 10, Exceptional, (7)
"Great location and comfortable"
On Shuttle, 12 min walk to village. King Beds with Private Baths
Bromley Aframe - King Master Bed, Wood Fireplace
Front of house - leaves changing in October peeping season

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
Classic Alpine Vermont Chalet
Exterior

Classic Alpine Vermont Chalet

10.0 out of 10, Exceptional, (10)
"We loved everything about this property. Lots of bedrooms, comfortable beds, big living room and kitchen area and very close to the downtown area. I highly recommend this house for large families looking for a place to stay in Vermont!"
Classic Alpine Vermont Chalet
Stratton-View Ski Retreat 10 Min to Stratton | Hot Tub
Today is the perfect bluebird day for skiing. Hit the slopes just moments away from our doorstep.

Stratton-View Ski Retreat 10 Min to Stratton | 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. "
Stratton-View Ski Retreat 10 Min to Stratton | Hot Tub
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
Interior

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

10.0 out of 10, Exceptional, (9)
"Just got back from three nights at this wonderful property with a group of 50-somethings to compete in a gravel bike race. This property was ideally located near our start line, very very clean, plenty of room for us, basically as advertised. Would definitely rent here again in the future given all of the above.."
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
Mid-Century Arty Chalet - 2 Min to Stratton Slopes
Living area

Mid-Century Arty Chalet - 2 Min to Stratton Slopes

Mid-Century Arty Chalet - 2 Min to Stratton Slopes
Perfect house surrounded by National Forest to get away and decompress!!!
Exterior

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

Perfect house surrounded by National Forest to get away and decompress!!!
Paradise Vermont, Nature Chalet With Indoor Hot Tub
Pool

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
Great room on main level

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.
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Other property types in Bennington

Perfect for Leaf Peeping w/Bar Room, Hot Tub
Bar Room

Perfect for Leaf Peeping w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (11)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Perfect for Leaf Peeping w/Bar Room, Hot Tub
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Skiing open now at Prospect Mountain Snowmobiling coming soon Book now before up

Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.

9.8 out of 10, Exceptional, (132)
"Linda was amazing from beginnin'g to end to ensure a comfortable stay. This house was beautiful and so cozy to stay in. The loft bed had a gorgous view of the lake and snow. Plenty of sleeping room for my kids.They got to play in the snow too:)"
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Nighttime view

Two Brooks Lodge, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (27)
"In town for a long weekend and loved the location. The owner was prompt and very helpful as we made a mistake in booking. FYI, The pictures are great but it’s a bit more rustic than they make it seem. Still, it was great to sit outside and hear the brooks flowing. Very quiet street! Housecleaning was a bit lacking though as there were some huge cobwebs in the corners. That was fine for us as we spend our time in a barn anyway. "
The price is SAR 638
SAR 1,338 total
includes taxes & fees
31 Dec - 1 January 2025
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
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.