Title: Top Chalets in  Windsor County in 2026 | Expedia.ca

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Photo by Rachel Samanyi

# Chalets in Windsor County

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## Check prices for these dates

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Cities in Windsor County

![Ludlow showing street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94298-Ludlow.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Ludlow

[](https://expedia.ca/Ludlow-Chalets.d8496-aaChalets.Travel-Guide-Accommodation)

![Woodstock featuring a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94311-Woodstock.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Woodstock

[](https://expedia.ca/Woodstock-Chalets.d10868-aaChalets.Travel-Guide-Accommodation)

![](https://mediaim.expedia.com/destination/2/212ecbf3b606238229538e223f3f57eb.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### White River Junction

[](https://expedia.ca/White-River-Junction-Chalets.d6294-aaChalets.Travel-Guide-Accommodation)

![](https://mediaim.expedia.com/destination/2/e6f5a135e5990faead3b19a2481c6d2b.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Windsor

[](https://expedia.ca/Windsor-Chalets.d7881-aaChalets.Travel-Guide-Accommodation)

![Quechee featuring a river or creek, a bridge and tranquil scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/93000/93816-Central-Vermont.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Quechee

[](https://expedia.ca/Quechee-Chalets.d9580-aaChalets.Travel-Guide-Accommodation)

![](https://mediaim.expedia.com/destination/2/6e1ce19989493034a8e8934b004054dd.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Norwich

[](https://expedia.ca/Norwich-Chalets.d184063-aaChalets.Travel-Guide-Accommodation)

## Our top choices for Windsor County chalets

![Exterior](https://images.trvl-media.com/lodging/71000000/70970000/70966100/70966049/4d9690a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/71000000/70970000/70966100/70966049/199efe63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, books, computer monitors](https://images.trvl-media.com/lodging/71000000/70970000/70966100/70966049/16b21755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70970000/70966100/70966049/d35194b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt. 

[](https://www.expedia.ca/Plymouth-Hotels-Black-Dog-Lodge-Secluded-Chalet.h70966049.Hotel-Information)

Plymouth

9.8/10

Exceptional

(25)

"The cabin was spacious and well stocked. It’s on a quiet dirt-road which made it perfect for our kids and dog to play and run outside. We really enjoyed our time close to some beautiful lakes, hikes and bike rides."

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

Fabienne M.

[](https://www.expedia.ca/Plymouth-Hotels-Black-Dog-Lodge-Secluded-Chalet.h70966049.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/72000000/71650000/71644000/71643979/a87186d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/72000000/71650000/71644000/71643979/bbf460e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71650000/71644000/71643979/0e3d7df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71650000/71644000/71643979/beb528b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

[](https://www.expedia.ca/Ludlow-Hotels-Delightful-Ski-Chalet-Minutes-To-Okemo.h71643979.Hotel-Information)

Ludlow

10/10

Exceptional

(40)

"This was our 2nd year in a row staying at Noreen’s place. The property is breathtaking, the house is well appointed with comfy beds, solid WiFi and a great kitchen. We had 6 adults and 7 kids and the space never felt cramped, but for us the real show stopper is the side yard and deck. Awesome views, one of the best fire pits I have ever seen and a lawn worthy of many kids games. Extra bonus this year was clear weather to see the Presides meteor shower at night. We can’t wait to stay again next...

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

Philip C.

[](https://www.expedia.ca/Ludlow-Hotels-Delightful-Ski-Chalet-Minutes-To-Okemo.h71643979.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/84000000/83540000/83534500/83534431/825ad102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/84000000/83540000/83534500/83534431/21b6d816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83540000/83534500/83534431/abdbc13f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83540000/83534500/83534431/883930ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Creekside Chalet centrally located near 4 ski resorts

[](https://www.expedia.ca/Weston-Hotels-Cozy-Creekside-Chalet-Centrally-Located-Near-4-Ski-Resorts.h83534431.Hotel-Information)

Weston

10/10

Exceptional

(16)

"An attractive home in a nice area. The hosts are very kind people and very accommodating. I would stay again. The location is convenient to many interesting places. "

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

Ed C.

[](https://www.expedia.ca/Weston-Hotels-Cozy-Creekside-Chalet-Centrally-Located-Near-4-Ski-Resorts.h83534431.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33503600/33503516/25573866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33503600/33503516/2fa9bab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33510000/33503600/33503516/d1f2c8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, Hulu](https://images.trvl-media.com/lodging/34000000/33510000/33503600/33503516/ab183130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

[](https://www.expedia.ca/Ludlow-Hotels-Gorgeous-Ski-Chalet-With-Game-Room-Hot-Tub-On-Okemo-Mt-Under-1-Mile-To-Base.h33503516.Hotel-Information)

Ludlow

9.8/10

Exceptional

(128)

"Spacious, clean, beautiful property, well-stocked, host extremely responsive "

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

Lisa D.

[](https://www.expedia.ca/Ludlow-Hotels-Gorgeous-Ski-Chalet-With-Game-Room-Hot-Tub-On-Okemo-Mt-Under-1-Mile-To-Base.h33503516.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/398175e4.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)

![Dining](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/fe4833a9.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/d82b1386.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

(10)

"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.

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

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33740000/33735500/33735418/ee75ce2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33740000/33735500/33735418/6dd1cdb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33740000/33735500/33735418/ebc65697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, stereo](https://images.trvl-media.com/lodging/34000000/33740000/33735500/33735418/b1d619f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Okemo Hideaway – Secluded Woodland Chalet 7 minutes to Slopes & Village

[](https://www.expedia.ca/Ludlow-Hotels-DISCOUNTED-RATES-AVAILABLE-10-To-15-Off-For-3-Or-More-Days-Booked.h33735418.Hotel-Information)

Ludlow

9.4/10

Exceptional

(23)

"We were up for a weekend in February. Perfect place. Plenty of beds. The hot tub was a bonus. Excellent communication by the hosts. "

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

Tom G.

[](https://www.expedia.ca/Ludlow-Hotels-DISCOUNTED-RATES-AVAILABLE-10-To-15-Off-For-3-Or-More-Days-Booked.h33735418.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/83000000/82840000/82835500/82835471/3023fe64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![8 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/83000000/82840000/82835500/82835471/9e904587.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82840000/82835500/82835471/ba18cf2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/83000000/82840000/82835500/82835471/807f004b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults

[](https://www.expedia.ca/Ludlow-Hotels-Ski-Inout-Chalet-On-Okemos-Sachem-Trail-Sleeps-22-Adults.h82835471.Hotel-Information)

ludlow

10/10

Exceptional

(29)

"Our stay was great! House was excellent, location was perfect, and Dave was super accommodating!"

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

Anna B.

[](https://www.expedia.ca/Ludlow-Hotels-Ski-Inout-Chalet-On-Okemos-Sachem-Trail-Sleeps-22-Adults.h82835471.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/40000000/39650000/39649600/39649525/fe4e54e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/40000000/39650000/39649600/39649525/6621ee37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/40000000/39650000/39649600/39649525/6ce552c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/40000000/39650000/39649600/39649525/b0740d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

[](https://www.expedia.ca/Woodstock-Hotels-Woodbridge-Inn-6BR-Historic-CharmRiverfrontHot-TubClose-To-Ski.h39649525.Hotel-Information)

Woodstock

10/10

Exceptional

(27)

"Great space for large family gathering! "

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

ted d.

[](https://www.expedia.ca/Woodstock-Hotels-Woodbridge-Inn-6BR-Historic-CharmRiverfrontHot-TubClose-To-Ski.h39649525.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/24000000/23930000/23927500/23927486/1e794e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/24000000/23930000/23927500/23927486/2d38a4a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/24000000/23930000/23927500/23927486/59fd1239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23930000/23927500/23927486/c8f8d62d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Okemo Mountain Chalet W/ Hot Tub and Game Room

[](https://www.expedia.ca/Ludlow-Hotels-Okemo-Mountain-Chalet-W-Hot-Tub-And-Game-Room.h23927486.Hotel-Information)

Ludlow

9.8/10

Exceptional

(161)

"Perfect for our multi-generational family get together!"

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

Michael B.

[](https://www.expedia.ca/Ludlow-Hotels-Okemo-Mountain-Chalet-W-Hot-Tub-And-Game-Room.h23927486.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)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/36b6b61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/0df9f82e.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)

### 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)

"Really enjoyed the setup at the location and the owners were very responsive to any queries!"

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

Ed N.

CA $347

CA $873 total

includes taxes & fees

Dec 18 - Dec 19

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

![Exterior](https://images.trvl-media.com/lodging/31000000/30400000/30397900/30397853/3264bc4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/31000000/30400000/30397900/30397853/be76101e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/31000000/30400000/30397900/30397853/f5cf98b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30400000/30397900/30397853/e99273ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

[](https://www.expedia.ca/Stockbridge-Hotels-Cozy.h30397853.Hotel-Information)

Stockbridge

9.6/10

Exceptional

(52)

"Beautiful property"

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

sheri n.

[](https://www.expedia.ca/Stockbridge-Hotels-Cozy.h30397853.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74010000/74006000/74005987/63e2a250.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/75000000/74010000/74006000/74005987/0e22f007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74010000/74006000/74005987/571f7854_edited_7762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Kitchen islands](https://images.trvl-media.com/lodging/75000000/74010000/74006000/74005987/8a011b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

[](https://www.expedia.ca/Ludlow-Hotels-Modern-7Bd3Ba-Mountain-Chalet-W-Hot-Tub.h74005987.Hotel-Information)

Ludlow

10/10

Exceptional

(10)

"Great house, made our ski weekend easy and fun. House is better than the pictures."

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

Trevor D.

[](https://www.expedia.ca/Ludlow-Hotels-Modern-7Bd3Ba-Mountain-Chalet-W-Hot-Tub.h74005987.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/21000000/20180000/20178200/20178157/264480ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20180000/20178200/20178157/40387fcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/21000000/20180000/20178200/20178157/eb09d128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/21000000/20180000/20178200/20178157/8f93d503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

[](https://www.expedia.ca/Woodstock-Hotels-Falcon-House-VT-Modern-Chalet-WSauna-On-60-Acres-Hiking-Bike-To-Village.h20178157.Hotel-Information)

West Woodstock

10/10

Exceptional

(71)

"The house was very clean and tidy. Kat was great at communicating and making sure we had everything we needed!"

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

Kevin P.

[](https://www.expedia.ca/Woodstock-Hotels-Falcon-House-VT-Modern-Chalet-WSauna-On-60-Acres-Hiking-Bike-To-Village.h20178157.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/95d08525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/efdfd8b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/98a04e79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/c33b35a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gnome Home Mountain Ski Chalet w/Sauna Killington

[](https://www.expedia.ca/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information)

Stockbridge

10/10

Exceptional

(4)

"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"

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

Gerald S.

CA $401

CA $812 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/65000000/64590000/64587700/64587644/8dcca8f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/65000000/64590000/64587700/64587644/w451h683x286y0-267606a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/65000000/64590000/64587700/64587644/45736a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/65000000/64590000/64587700/64587644/000fe984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow

[](https://www.expedia.ca/Cavendish-Hotels-Cozy-Mountain-View-Chalet-Near-Okemo.h64587644.Hotel-Information)

Cavendish

10/10

Exceptional

(14)

"We had a fantastic stay at the Honeycomb Hideout. The house is very well maintained and has everything you need. The weather didn't hold out for us but having a great place to stay made up for it!"

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

Michael K.

[](https://www.expedia.ca/Cavendish-Hotels-Cozy-Mountain-View-Chalet-Near-Okemo.h64587644.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93500000/93497900/93497853/2d4478f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93500000/93497900/93497853/757d573a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/94000000/93500000/93497900/93497853/1eda37b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93500000/93497900/93497853/b9149846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain

[](https://www.expedia.ca/Chester-Hotels-Modern-Chalet-With-Serene-Views-15-Minutes-To-Okemo-Mountain.h93497853.Hotel-Information)

Chester

9.2/10

Wonderful

(5)

"We had a blast and had fund using the hot tub and firepit."

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

Victoria H.

[](https://www.expedia.ca/Chester-Hotels-Modern-Chalet-With-Serene-Views-15-Minutes-To-Okemo-Mountain.h93497853.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/110000000/109560000/109551000/109550902/w3072h2045x0y1-d19d2a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109560000/109551000/109550902/w3071h2045x1y1-054ee8e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109560000/109551000/109550902/w3070h2046x0y0-9adc0a1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109560000/109551000/109550902/w3071h2045x1y1-c1371560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5-bedroom chalet with AC and WiFi in charming Chester

[](https://www.expedia.ca/Chester-Hotels-Spacious-5-Bedroom-Chalet-With-AC-And-WiFi-In-Charming-Chester.h109550902.Hotel-Information)

Chester

10/10

Exceptional

(8)

"Girls family weekend, relaxing, visiting and enjoying the hot tub."

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

Sarah D.

[](https://www.expedia.ca/Chester-Hotels-Spacious-5-Bedroom-Chalet-With-AC-And-WiFi-In-Charming-Chester.h109550902.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115079500/115079418/c2223ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/116000000/115080000/115079500/115079418/f3706d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115080000/115079500/115079418/81b165db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115080000/115079500/115079418/6d245584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Views. Hot Tub. , 5 Wooded Acres. Private Pond

[](https://www.expedia.ca/Plymouth-Hotels-New-Construction-Post-And-Beam.h115079418.Hotel-Information)

Plymouth

[](https://www.expedia.ca/Plymouth-Hotels-New-Construction-Post-And-Beam.h115079418.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/45000000/44920000/44910100/44910019/4f669d5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Chalet | Private kitchen](https://images.trvl-media.com/lodging/45000000/44920000/44910100/44910019/d630ac73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Chalet | Living room](https://images.trvl-media.com/lodging/45000000/44920000/44910100/44910019/3b878475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/45000000/44920000/44910100/44910019/297574cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bent Tree

[](https://www.expedia.ca/Stockbridge-Hotels-Bent-Tree.h44910019.Hotel-Information)

Stockbridge

[](https://www.expedia.ca/Stockbridge-Hotels-Bent-Tree.h44910019.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.

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## Find vacation rentals that suit your style

Cabins

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Apartments

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Condos

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Chalets

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Villas

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## Top Windsor County Hotel Reviews

![The Vesper ](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/ae1d5a64_y.jpg)

### The Vesper 

10/10 Excellent

"We were in town for Wassail Weekend. The Vesper was a great place to stay. The location was so close to all of the fun activities and restaurants. Jessica was very accommodating and friendly. Would recommend! "

[](https://expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.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

"Clean rooms, front desk personal could use people skill update, not young lady there this am, she was great. Guys in restaurant were the best. "

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

![Best Western Springfield Hotel](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/f0e2c480_y.jpg)

### Best Western Springfield Hotel

10/10 Excellent

"All very good. "

[](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information)

![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg)

### Woodstock Inn & Resort

10/10 Excellent

"I stay at Woodstock Inn every December and it never disappoints. The rooms are comfortable and well-appointed, but it's hard to decide whether to enjoy the comforts of the room or sitting in front if the fire in the lobby. I look forward to the next visit."

[](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information)

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

### The Shire Woodstock

10/10 Excellent

"The staff was super nice and flexible! Location was great "

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

"Yea"

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

![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg)

### Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"Clean room, very nice staff, everything was excellent! "

[](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information)

![Hotel Coolidge](https://images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg)

### Hotel Coolidge

10/10 Excellent

"Spacious, quirky and historical accommodations. Staff was great, amenities were just as described. Room was actually better than I had anticipated "

[](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.Hotel-Information)

![COHO Inn & Motor Lodge](https://images.trvl-media.com/lodging/105000000/104400000/104395800/104395732/3f7fd5fb_y.jpg)

### COHO Inn & Motor Lodge

10/10 Excellent

"I stayed at here on a whim in December ‘25 on an early ski trip to Stratton & Killington, looking for a spot that wouldn’t break the bank. Got a whole lot more than I bargained for! Eggs & bacon for breakfast, super cozy cabin, great hospitality, and good recommendations. New owners Ali & Lane are hard at work investing more and more into the place and I can’t wait to go back in the summer. Highly recommend for anyone seeking an unfussy stay with rustic charm and super-welcoming owner/operators."

[](https://expedia.ca/Weston-Hotels-The-Colonial-House-Inn-And-Motor-Lodge.h104395732.Hotel-Information)

## Find out more about Windsor County

## Windsor County Chalets information

| Number of reviews | 530        |
| ----------------- | ---------- |
| Accommodation     | 23 Chalets |
| Lowest Price      | CA $812    |
| Highest Price     | CA $873    |

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- [Billings Farm and Museum ](https://www.expedia.ca/Billings-Farm-And-Museum-Woodstock.d6175222.Vacation-Attraction)
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