Chester Chalets from CA $508

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Our top choices for Chester chalets

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

1. Mountain Chalet, sleeps 8, with hot tub

Peru

Michael B.

CA $1,042 total

includes taxes & fees

Nov 16 - Nov 17

A white, single-story cabin with a red door, surrounded by trees.

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

Jamaica

fran g.

CA $1,434 total

includes taxes & fees

Nov 9 - Nov 10

A wooden house with a porch lit by string lights, surrounded by snow.

3. Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Chelsea G.

CA $508 total

includes taxes & fees

Nov 9 - Nov 10

A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

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

Wardsboro

Jeff H.

CA $562 total

includes taxes & fees

Nov 9 - Nov 10

A wooden deck with a table and chairs, surrounded by a forest.

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

Wardsboro

Carly L.

CA $603 total

includes taxes & fees

Nov 9 - Nov 10

A small, single-story house with a front porch, a red door, and a white fence.

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

Wardsboro

Lisa B.

CA $656 total

includes taxes & fees

Nov 9 - Nov 10

A two-story wooden house with a stone retaining wall, a covered porch, and a small shed.

7. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Dover

Brian S.

CA $695 total

includes taxes & fees

Nov 30 - Dec 1

A two-story wooden cabin with a stone foundation, large windows, and a stone chimney.

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

Stratton

samantha b.

CA $1,033 total

includes taxes & fees

Nov 9 - Nov 10

A hot tub on a wooden deck with a view of autumn trees.

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

Dover

Liz E.

CA $1,045 total

includes taxes & fees

Nov 9 - Nov 10

A two-story house with a large deck and a covered porch, surrounded by trees and a grassy yard.

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

Dover

Andrew B.

CA $710 total

includes taxes & fees

Nov 10 - Nov 11

11. NEW Private Chalet - 4 mins to Mt Snow

Dover

Mark C.

CA $912 total

includes taxes & fees

Nov 9 - Nov 10

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Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"Lovely location. Happy, attentive staff, quiet, lots of parking. Definitely go back again. Only problem was the hotel and room was very warm. The staff gladly provided a fan."

Woodstock Inn & Resort

10/10 Excellent

"Fantastic stay at Woodstock Inn this week! The room and property were spotless, and the staff was incredibly kind and welcoming. The spa was beautiful, the food at Red Rooster was excellent, and the athletic center, pool, and hot tub were all great. The entire property has a quiet, peaceful atmosphere that makes it easy to relax and unwind. Would absolutely recommend!"

Hideaway Inn Mt. Snow

10/10 Excellent

"The room was small and simple, but nicely decorated, including a record player with a vinyl album (cover, at least; didn't check for actual vinyl). The room was warm and the place was quiet when I stayed, which was off-season. I've been pulling into the parking lot of this place for five years now (MOOver), so staying there was interesting for me. I stayed there during a HAZMAT spill that closed Woodford Mtn for a couple days. Of special note, this is the ONLY hotel I've ever stayed at that had a sleep/sound machine in the room. I ALWAYS take one with me when traveling, but this was a last minute decision, so I would've had to pull up something on my phone, but there was a nice sound machine on the nightstand and I used it. Those are so helpful when staying in hotels/inns."

Stone Hearth Inn and Eatery

8/10 Good

"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 nights because of the difficulty of the stairs… It was however nice if no handicaps"

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10/10 Excellent

"This is an adorable and cozy cabin surrounded by nature - from which you can hear a soothing stream from your window. If you are looking for a place to restore in nature and unplug "glamping-style" - yet close to shops/coffee/outings, etc., - this little blue cabin is the perfect spot. I liked that they provided the option to unplug the wi-fi, if needed, to save solar electricity and/or just truly unplug."

Find out more about Chester

Chester Chalets information

Number of reviews	126
Accommodation	94 Chalets
Lowest Price	CA $508
Highest Price	CA $1,434

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester chalets

1. Mountain Chalet, sleeps 8, with hot tub

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

3. Chalet Mount Snow/Stratton Skiing/hiking

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

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

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

7. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

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

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

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

11. NEW Private Chalet - 4 mins to Mt Snow

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Days Inn by Wyndham Keene NH

Woodstock Inn & Resort

On The River Inn

Hideaway Inn Mt. Snow

The Equinox Golf Resort And Spa

Grand Summit Resort, A Vail Resorts Property

Stone Hearth Inn and Eatery

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Find out more about Chester

Chester Chalets information

Explore a world of travel with Expedia

Search Chalets in Chester from CA $508

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester chalets

1. Mountain Chalet, sleeps 8, with hot tub

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

3. Chalet Mount Snow/Stratton Skiing/hiking

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

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

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

7. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

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

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

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

11. NEW Private Chalet - 4 mins to Mt Snow

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Find out more about Chester

Chester Chalets information

Explore a world of travel with Expedia