Title: Chester Chalets from CA $369 | Expedia.ca

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester chalets

![Exterior](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/398175e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/40bc0fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/13b3aaae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/97cdf1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

[](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.Hotel-Information)

Chester

10/10

Exceptional

(11 reviews)

"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carla C.

CA $380

CA $744 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/a3e005f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/407a0d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/6a20b4d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/cc9b5501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stratton A-Frame: Hot Tub Sauna EV Boot Warmers 1 Gbps Manchester Okemo MT Snow

[](https://www.expedia.ca/Jamaica-Hotels-PreLaunch-A-Frame-Hot-Tub-Sauna-EV-Stratton.h120429915.Hotel-Information)

Jamaica

10/10

Exceptional

(2 reviews)

"Couldn't be better! Outstanding! We had our family holiday ski trip from Dec 25-29th,2025\. The amenities were second to none. The hot tub, sauna and fire pit made the winter warm! The house was clean comfortable and very cozy. The kitchen was extremely well appointed (sharp knives!). The staples available (coffee, tea, oil, spices etc.) were high quality and the best I've ever experienced in a short term rental. The beds and bedding were very comfortable! Most immortality the hosts were very...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Laird N.

CA $586

CA $1,376 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Jamaica-Hotels-PreLaunch-A-Frame-Hot-Tub-Sauna-EV-Stratton.h120429915.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/5f637af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/4c3f61c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/dcc44385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/38bc7f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

[](https://www.expedia.ca/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.Hotel-Information)

Dover

10/10

Exceptional

(15 reviews)

"This place was absolutely amazing! The pictures didn’t do this place justice. The ambience of the deck at night was magical. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kaymari T.

CA $679

CA $1,334 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/cc65421b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/7d6bcc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/83acf129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/31c838bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private cabin: 7 mins to slopes, wood fireplace

[](https://www.expedia.ca/West-Dover-Hotels-Private-Cabin-7-Mins-To-Slopes.h105982869.Hotel-Information)

Dover

9.8/10

Exceptional

(6 reviews)

"We spent the week, excellent location and the home was exactly as described in listing."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris R.

CA $501

CA $1,104 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/West-Dover-Hotels-Private-Cabin-7-Mins-To-Slopes.h105982869.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/d74e8c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/fdf153b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/deccb16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/74c46c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

[](https://www.expedia.ca/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.Hotel-Information)

Stratton

10/10

Exceptional

(5 reviews)

"We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nicholas D.

CA $536

CA $1,142 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/c71f56f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/7665cd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, Netflix, streaming services](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/341be75e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/26cdcbb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information)

Dover

9.8/10

Exceptional

(22 reviews)

"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

SZU YIN C.

CA $143

CA $595 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1071x0y2-62744863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, foosball, books](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/84b8211e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/8581675a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1070h1076x5y0-75daf8bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/West-Dover-Hotels-Gorgeous-4-Bedroom-3-Bath-Chalet-In-Dover-10-Minutes-To-Mount-Snow-WIFI.h112675182.Hotel-Information)

Dover

10/10

Exceptional

(7 reviews)

"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris I.

CA $339

CA $831 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/West-Dover-Hotels-Gorgeous-4-Bedroom-3-Bath-Chalet-In-Dover-10-Minutes-To-Mount-Snow-WIFI.h112675182.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/76d2f10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/94109ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/3a0b064f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/f158318f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus

[](https://www.expedia.ca/West-Dover-Hotels-Brand-New-Hot-Tub.h109550875.Hotel-Information)

Dover

10/10

Exceptional

(10 reviews)

"Helpful, fun and warm. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anthony S.

CA $645

CA $1,450 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/West-Dover-Hotels-Brand-New-Hot-Tub.h109550875.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/eda7773c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/ec10883e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/e051b2f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/f7ab718d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.Hotel-Information)

Wardsboro

10/10

Exceptional

(16 reviews)

"We had an awesome time here. The property was well stocked with essentials, affordable us some opportunity to unwind, explore the creek, and hang out with the fire pit, board games, and the kids enjoyed the ridge racer arcade. Would absolutely come back!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joseph R.

CA $280

CA $644 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/63238a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/ad2f042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/ba81a7b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/df964608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

[](https://www.expedia.ca/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.Hotel-Information)

Plymouth

10/10

Exceptional

(14 reviews)

"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julie-Anne B.

CA $369

CA $910 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/6da0ce7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/d54b3197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/62ad9b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/3bd9f0bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Wardsboro-Hotels-The-Mont-Haus-Minutes-To-Mt-Snow-Stratton.h113092281.Hotel-Information)

Wardsboro

10/10

Exceptional

(5 reviews)

"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kristen T.

CA $321

CA $768 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Wardsboro-Hotels-The-Mont-Haus-Minutes-To-Mt-Snow-Stratton.h113092281.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/fe04814b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/f1c572ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/a1a0916f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/ef743cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

[](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information)

West Dover

10/10

Exceptional

(23 reviews)

"Wonderful time..the home was very spacious and comfortable..great location!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ellen P.

CA $333

CA $961 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/a6a78255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/1ce3fb4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/bcfc0861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/b3ddab44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet Mount Snow/Stratton Skiing/hiking

[](https://www.expedia.ca/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information)

East Dover

9.8/10

Exceptional

(10 reviews)

"Easy to find! Clean! Cozy!! Would definitely stay again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Roy-michael G.

CA $155

CA $595 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/0d4d95fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/97a2d51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/33af9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/w2180h1456x4y0-3d3ff46c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW Private Chalet - 4 mins to Mt Snow

[](https://www.expedia.ca/West-Dover-Hotels-NEW-Private-Chalet-4-Mins-To-Mt-Snow.h110980715.Hotel-Information)

Dover

10/10

Exceptional

(2 reviews)

"Mary and Adam were absolutely lovely hosts! From the initial booking to check-in and throughout our stay, they were incredibly responsive. The house was fantastic—completely updated, with a fully equipped kitchen, spacious bedrooms, and a beautiful living area with a cozy fireplace.Our only regret is that we couldn’t stay longer. Thank you, Mary and Adam, for a wonderful stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Patricia N.

CA $335

CA $910 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/West-Dover-Hotels-NEW-Private-Chalet-4-Mins-To-Mt-Snow.h110980715.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496357/c179d1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496357/7e02a3bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496357/b3bdf68d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496357/8f85f7fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

[](https://www.expedia.ca/Jamaica-Hotels-Mountain-Chalet-7min-To-Ski-Stratton-WoodStove.h108496357.Hotel-Information)

Jamaica

7.0/10

Good

(2 reviews)

"Its a cabin. Very fun for a group of friends. I wouldnt bring a family here. No running water in the morning"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hugo T.

CA $205

CA $369 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Jamaica-Hotels-Mountain-Chalet-7min-To-Ski-Stratton-WoodStove.h108496357.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/83000000/82830000/82822100/82822044/f19f2000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/83000000/82830000/82822100/82822044/c8dd373f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/83000000/82830000/82822100/82822044/15e24370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/83000000/82830000/82822100/82822044/31e1efc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Green Mountain Manor - Ski and Summer Chalet

[](https://www.expedia.ca/Bondville-Hotels-Shuttle-Access-Ski-House.h82822044.Hotel-Information)

Winhall

9.8/10

Exceptional

(7 reviews)

"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jay T.

CA $4,853

CA $6,868 total

includes taxes & fees

Feb 21 - Feb 22

[](https://www.expedia.ca/Bondville-Hotels-Shuttle-Access-Ski-House.h82822044.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-17&endDate=2026-02-18&regionId=89014&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

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Private vacation homes

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Cottages

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Condos

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Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=APARTMENT)

Aparthotels

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Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=CHALET)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=VILLA)

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## Top Chester Hotel Reviews

![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg)

### The Shire Woodstock

10/10 Excellent

"Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!"

[](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information)

![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg)

### Hampton Inn and Suites Manchester

10/10 Excellent

"Staff was great! Used the business office which was easily accessible, location is great! "

[](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information)

![Bromley View Inn](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/85d1c6cb_y.jpg)

### Bromley View Inn

10/10 Excellent

"Clean room/ great breakfast"

[](https://expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information)

![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg)

### The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"Awesome stay thank you"

[](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information)

![Long Trail House at Stratton Mountain Resort](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/31db03a1_y.jpg)

### Long Trail House at Stratton Mountain Resort

10/10 Excellent

"Nice place and great location!!!"

[](https://expedia.ca/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information)

![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg)

### Pointe at Castle Hill Resort

10/10 Excellent

"Friendly staff, clean rooms. "

[](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information)

![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg)

### The Manchester View

10/10 Excellent

"The MV was perfect for a getaway to the southern greens for snow. Place was clean, great water pressure, and heat. Had to upgrade my room and it wasn't a problem. Looking forward to coming back. "

[](https://expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information)

![Big Bears Lodge](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/5147c108_y.jpg)

### Big Bears Lodge

10/10 Excellent

"Yes "

[](https://expedia.ca/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information)

![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg)

### On The River Inn

10/10 Excellent

"Everything was great from the room to the staff making everything as convenient as possible."

[](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information)

## Find out more about Chester

## Chester Chalets information

| Number of reviews | 138         |
| ----------------- | ----------- |
| Accommodation     | 102 Chalets |
| Lowest Price      | CA $369     |
| Highest Price     | CA $6,868   |

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