A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Bennington Chalets

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    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Bennington chalets

A two-story wooden house with a porch, surrounded by snow-covered trees.

1. Tranquil Brookside Retreat with Hot Tub & Firepit

Tranquil Brookside Retreat with Hot Tub & Firepit
Peru
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
$649 nightly
The price is $728
Nov 10 - Nov 11
Total with taxes and fees
Tranquil Brookside Retreat with Hot Tub & Firepit
A two-story wooden house with a stone retaining wall, a covered porch, and a small shed.

2. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.4 out of 10, Exceptional, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
$440 nightly
The price is $498
Nov 30 - Dec 1
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A wooden house with a porch lit by string lights, surrounded by snow.

3. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy, set back and had all the amenities that you would need"
United States
Chelsea G.
$321 nightly
The price is $363
Nov 4 - Nov 5
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A wooden cabin with a front porch, surrounded by a forest.

4. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (14 reviews)
"Loved this place so much! Adorable spot, quaint but has everything you need. Loved the luxury details. "
United States
Carly L.
$410 nightly
The price is $463
Nov 4 - Nov 5
Total with taxes and fees
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

5. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (20 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
$355 nightly
The price is $401
Nov 4 - Nov 5
Total with taxes and fees
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A two-story house with a large deck and a covered porch, surrounded by trees and a grassy yard.

6. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (7 reviews)
"Perfect spot for a family ski vacation! Thanks you for behind a great host!"
United States
Andrew B.
$842 nightly
The price is $951
Nov 4 - Nov 5
Total with taxes and fees
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
A small, single-story house with a front porch, a red door, and a white fence.

7. The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm

The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
Wardsboro
9.6 out of 10, Exceptional, (4 reviews)
"Everything was wonderful and perfect for our family. Super clean and great Vermont experience"
United States
Lisa B.
$395 nightly
The price is $446
Nov 4 - Nov 5
Total with taxes and fees
The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
A spacious living room with a fireplace, blue sofas, a leather armchair, and a ceiling fan.

8. Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna

Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna
Stratton
10.0 out of 10, Exceptional, (7 reviews)
"Everything about our stay was top notch. Highly recommend and I will book this house again. "
United States
samantha b.
$652 nightly
The price is $737
Nov 4 - Nov 5
Total with taxes and fees
Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna
A red wooden house with multiple windows and a front door, surrounded by trees and a stone pathway.

9. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!"
United States
Georgia P.
$1,122 nightly
The price is $1,253
Nov 16 - Nov 17
Total with taxes and fees
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
A white, single-story cabin with a red door, surrounded by trees.

10. Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna

Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Great peaceful stay. Hosts were always in communication with us. Close to Stratton. Hot tube & sauna were a great top off to a day of skiing. "
United States
fran g.
$833 nightly
The price is $941
Nov 9 - Nov 10
Total with taxes and fees
Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna
Exterior

11. NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Great place close enough to everything you need but set off the road for quiet evenings. Clean, spacious open floor plan great accommodation that checks all the needs for a ski getaway. "
United States
Mark C.
$571 nightly
The price is $646
Nov 4 - Nov 5
Total with taxes and fees
NEW Private Chalet - 4 mins to Mt Snow
A two-story cabin with a deck, large windows, and a hot tub.

12. Chalet 1mi to Mount Snow with cinema and hot tub

Chalet 1mi to Mount Snow with cinema and hot tub
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Awesome stay!"
United States
Liz E.
$667 nightly
The price is $754
Nov 10 - Nov 11
Total with taxes and fees
Chalet 1mi to Mount Snow with cinema and 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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Top Bennington Hotel Reviews

Cozy Loft steps from VT Downtown

Cozy Loft steps from VT Downtown

10/10 Excellent
"Chris’ place was so great to stay at. Communication was on point and it looks MUCH better in real life. Was such a cozy weekend getaway I’d love to be back"
Anastasiia P. 3-night trip
Posted 4 days ago
Cozy Loft steps from VT Downtown

Find out more about Bennington

Bennington Chalets information

Number of reviews
128
Accommodation
15 Chalets
Lowest Price
$363
Highest Price
$1,253

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