The Best Chester, VT Chalets from $392

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Our top choices for Chester chalets

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

1. Tranquil Brookside Retreat with Hot Tub & Firepit

Peru

Michael B.

$641 nightly

Nov 10 - Nov 11

Total with taxes and fees

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.

$926 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

3. Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Chelsea G.

$346 nightly

Nov 8 - Nov 9

Total with taxes and fees

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.

$366 nightly

Nov 9 - Nov 10

Total with taxes and fees

A wooden cabin with a front porch, surrounded by a forest.

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

Wardsboro

Carly L.

$410 nightly

Nov 9 - Nov 10

Total with taxes and fees

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.

$414 nightly

Nov 8 - Nov 9

Total with taxes and fees

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.

$440 nightly

Nov 30 - Dec 1

Total with taxes and fees

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

Stratton

samantha b.

$652 nightly

Nov 8 - Nov 9

Total with taxes and fees

A two-story cabin with a deck, large windows, and a hot tub.

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

Dover

Liz E.

$663 nightly

Nov 10 - Nov 11

Total with taxes and fees

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.

$466 nightly

Nov 9 - Nov 10

Total with taxes and fees

11. NEW Private Chalet - 4 mins to Mt Snow

Dover

Mark C.

$571 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Top Chester Hotel Reviews

On The River Inn

10/10 Excellent

"We loved our spacious room, the sauna, pool/hot tub and game room! We were welcomed with a s’mores pack and spent the evening by the cozy fire pit. Lovely hotel!"

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	95 Chalets
Lowest Price	$392
Highest Price	$1,047

Room 1

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Our top choices for Chester chalets

1. Tranquil Brookside Retreat with Hot Tub & Firepit

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

On The River Inn

The Manchester View

Hideaway Inn Mt. Snow

The Equinox Golf Resort And Spa

Woodstock Inn & Resort

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

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