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Compare 23 Chalets in Bennington with updated reviews, rates, and availability.

Beautiful Manchester VT Mountain Retreat w/Hot Tub
10.0 out of 10, Exceptional, (22)
"Beautiful home, very clean, great hosts"
Beautiful Manchester VT Mountain Retreat w/Hot Tub
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
Exterior
BOGO Sale, Golf, Hiking, pool table, pac man, 4bedrooms with private baths.
10.0 out of 10, Exceptional, (4)
"Excellent home to reconnect with family when not on the slopes!! Hosts were the best!! Thank you!!!"
The price is SAR 694
SAR 2,005 total
includes taxes & fees
4 Jum. II - 5 Jum. II
BOGO Sale, Golf, Hiking, pool table, pac man, 4bedrooms with private baths.
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Open Living room
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
9.6 out of 10, Exceptional, (44)
"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.
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
Aerial view
Green Mountain Manor - Ski and Summer Chalet
10.0 out of 10, Exceptional, (6)
"The house is huge and has a giant finished basement perfect for the kids to retreat to. The kitchen had every appliance you can think of and the pizza oven worked perfectly. Hot tub outside was the icing on the cake after a day of skiing. The kids were also sledding on the golf course. The shuttle that comes right to the house made this super easy to get everyone to the mountain together. Will definitely stay again! Maybe for a golf retreat next time."
Green Mountain Manor - Ski and Summer Chalet
Exterior
Brian Piece of Heaven for fall Foliage. Beautiful colors
9.6 out of 10, Exceptional, (25)
"We had everything we needed and enjoyed our stay! Thanks Brian!"
Brian Piece of Heaven for fall Foliage. Beautiful colors
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
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, (7)
"The home was clean and comfortable, the owner was very responsive and accommodating, and the location of the home was perfect - secluded and surrounded by beauty, but a quick drive to Manchester Center and other interesting places to visit. I recommend it highly."
Serene & Stylish Chalet w/ HOT TUB near Manchester
Open living area - fireplace and dining area
Bromley Aframe - King Master Bed, Wood Fireplace
10.0 out of 10, Exceptional, (11)
"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
3 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
Exterior
Classic Alpine Vermont Chalet
10.0 out of 10, Exceptional, (8)
"Fit the bill for our group of 8 skiing at Stratton for the weekend. Quirky decor and foosball table were a plus. Easy check in/check out"
Classic Alpine Vermont Chalet
Exterior
10 min from Stratton! Log Cabin w/ Beautiful Views
10.0 out of 10, Exceptional, (9)
"We had a wonderful stay at this property. The proximity to Stratton along with the amazing view that we woke up to every morning could not be better. The only 2 things that I would have liked would have been for there to be a television (there was a monitor in the bedroom that we moved into the living room to stream from Chromebook) and an actual fireplace instead of wood burning stove but to be clear those are not complaints nor eif just a wish list. I would definitely recommend this property."
10 min from Stratton! Log Cabin w/ Beautiful Views
Open the umbrella for shade in the summer.
Mountain Retreat Getaway 5 Min to Swimming Pond
10.0 out of 10, Exceptional, (1)
"Our family had a great vacation here. We were at the mountain a lot during the day and this was the perfect place to come back to. It’s so close you can come back half day for a break before you hit the slopes for more. The house was very clean and had all the amenities we needed. There is a beautiful mountain view from the house. Highly recommend."
Mountain Retreat Getaway 5 Min to Swimming Pond
Interior
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
10.0 out of 10, Exceptional, (8)
"We stayed here for 3 nights to enjoy our first time skiing Stratton mountain. The house was very clean, comfortable and very close to the mountain. Beautiful views of the mountain from the house, nice fireplace and TV to enjoy at night."
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
Spacious living room
Stylish Mountain Getaway close to Stratton w/ Spa
10.0 out of 10, Exceptional, (5)
"We recently stayed at this VRBO rental property the last week of March 2024. It was 3 couples (6 adults), with 4 children (ages 9-13) - and the home was perfect for our group. We skied Stratton Mountain, which was less than 20 minutes away, and visited a spa / went shopping / ate at restaurants in nearby Manchester. The fireplace is fantastic - we spent afternoons and evenings after a day on the slopes cozied up around the fireplace. The game room - with shuffleboard, pool table and ping table...
Stylish Mountain Getaway close to Stratton w/ Spa
Living area
Mid-Century Modern Chalet in Stratton Mountain - 2 min from slopes
Mid-Century Modern Chalet in Stratton Mountain - 2 min from slopes
Exterior
Perfect House for Leaf Peeping.
Perfect House for Leaf Peeping.
Property grounds
Cheerful 4-bedroom chalet close to Ski slopes
9.0 out of 10, Wonderful, (2)
"Very welcoming, very, very well stocked home (fully stocked spice rack even). Perfect for two families on a quiet unpaved road. Less than a minute from the main road, but blissfully quiet. Easy access to Manchester, Londonderry, Weston, etc."
Cheerful 4-bedroom chalet close to Ski slopes
Pool
Paradise Vermont, Nature Chalet With Indoor Hot Tub
Paradise Vermont, Nature Chalet With Indoor Hot Tub
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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.

Other property types in Bennington

Front Porch
Victorian Home in Bennington, Vermont
10.0 out of 10, Exceptional, (78)
"The house fit our needs so well that we stayed an extra day. High ceilings, lots of light, more than ample room. We used it as a home base for ski slopes less than an hour away. Great work-from-home setup for a non-skier. Thank you for hosting us!"
Victorian Home in Bennington, Vermont
Bar Room
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
9.8 out of 10, Exceptional, (7)
"Beautiful property! Responsive and helpful hosts. Short walk into downtown Bennington. We had a blast!"
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Nighttime view
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
9.0 out of 10, Wonderful, (24)
"The cabin was clean and quiet and suited our needs for the weekend. The hot tub was enjoyable, although I would recommend that the owners purchase stairs to make exit and entry a bit easier."
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.

Recent reviews of Bennington hotels
Expedia verified reviews

Bennington Motor Inn

Bennington Motor Inn

5/5 Excellent
"Great stay at Bennington Motor Inn! "
A verified traveler from New York stayed at Bennington Motor Inn
Posted 4 days ago
Bennington Motor Inn