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

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![Must stop while in Vermont #autumn  #fall #roadtrip #travel #adventure #colorful  #vermont ](https://images.trvl-media.com/place/3000459649/24ffd150-771e-42f6-8fd9-a3002aef691c.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Rachel Samanyi

![](https://images.trvl-media.com/place/3000459649/24ffd150-771e-42f6-8fd9-a3002aef691c.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[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 two months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-05-22&endDate=2026-05-24&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://images.trvl-media.com/place/8496/505d08ac-b11f-4f25-a539-2958ea0722b2.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://images.trvl-media.com/place/10868/c2d6773f-8f3f-4c1a-b710-f2f2bceab647.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Woodstock

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

![Quechee Gorge- Vermont
#autumn #colorful #roadtrip #weekendgetaway #travel #adventure #nature #vacation ](https://images.trvl-media.com/place/3000459649/7d354301-07a8-4d26-bfd8-54320ed05c30.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### White River Junction

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

![Quechee featuring a river or creek, a bridge and tranquil scenes](https://images.trvl-media.com/place/9580/a3d99a95-3156-473d-99ae-f796cac4afe4.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Quechee

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

![Cornish-Windsor Covered Bridge](https://images.trvl-media.com/place/7881/cd323da6-a215-45d8-82e1-e1768184197a.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Windsor

[](https://expedia.ca/Windsor-Chalets.d7881-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)

![Smart TV, video games, books, computer monitors](https://images.trvl-media.com/lodging/71000000/70970000/70966100/70966049/59944392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, books, computer monitors](https://images.trvl-media.com/lodging/71000000/70970000/70966100/70966049/6f572bad.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)

### 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

(28 reviews)

"Great pet friendly property perfectly located between Woodstock and Killington. "

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

Norman Y.

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

![Property grounds](https://images.trvl-media.com/lodging/72000000/71650000/71644000/71643979/3ae797cd.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)

![Interior](https://images.trvl-media.com/lodging/72000000/71650000/71644000/71643979/7245eec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71650000/71644000/71643979/a87186d5.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

(44 reviews)

"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)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83540000/83534500/83534431/d8d782e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83540000/83534500/83534431/c0eaa646.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83540000/83534500/83534431/b0e20853.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)

### 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 reviews)

"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)

![Outdoor spa tub](https://images.trvl-media.com/lodging/34000000/33510000/33503600/33503516/e1cc1c95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33510000/33503600/33503516/832a7915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, Hulu](https://images.trvl-media.com/lodging/34000000/33510000/33503600/33503516/75c61d5f.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

(130 reviews)

"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)

![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)

![Interior](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/2a2bd0e5.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)

### 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 $370

CA $734 total

includes taxes & fees

Feb 2 - Feb 3

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

![Outdoor spa tub](https://images.trvl-media.com/lodging/34000000/33740000/33735500/33735418/df814428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, stereo](https://images.trvl-media.com/lodging/34000000/33740000/33735500/33735418/991631e6.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)

![Exterior](https://images.trvl-media.com/lodging/34000000/33740000/33735500/33735418/0ffa08bb.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

(25 reviews)

"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/83000000/82840000/82835500/82835471/629f7098.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)

![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/83000000/82840000/82835500/82835471/7933ad01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82840000/82835500/82835471/8cb2c6ca.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

(30 reviews)

"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/d6a58c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39650000/39649600/39649525/9dad2ff1.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)

![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 reviews)

"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)

![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23930000/23927500/23927486/c0ffd596.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)

![Smart TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/24000000/23930000/23927500/23927486/29303fef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/24000000/23930000/23927500/23927486/83d70fad.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 reviews)

"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)

![Dining](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/0c516aaf.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)

![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)

### 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 $368

CA $906 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/31000000/30400000/30397900/30397853/3264bc4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/31000000/30400000/30397900/30397853/e4a6dee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/31000000/30400000/30397900/30397853/74677f57.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)

### 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 reviews)

"Private, great location, clean, comfortable, warm host"

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

Marge S.

[](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)

![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)

![Dining](https://images.trvl-media.com/lodging/75000000/74010000/74006000/74005987/8e1db3eb_edited_b986.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 reviews)

"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)

![Outdoor dining](https://images.trvl-media.com/lodging/21000000/20180000/20178200/20178157/8f93d503.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)

![Exterior detail](https://images.trvl-media.com/lodging/21000000/20180000/20178200/20178157/b3403a6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/21000000/20180000/20178200/20178157/44e0cf72.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

(73 reviews)

"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/88000000/87520000/87515500/87515446/48be0320.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)

![TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/b2a8b57e.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 reviews)

"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 $323

CA $718 total

includes taxes & fees

Feb 2 - Feb 3

[](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/65000000/64590000/64587700/64587644/45736a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/65000000/64590000/64587700/64587644/deec2e9b.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)

### 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

(16 reviews)

"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)

![Exterior](https://images.trvl-media.com/lodging/94000000/93500000/93497900/93497853/c8c80513.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)

![Interior](https://images.trvl-media.com/lodging/94000000/93500000/93497900/93497853/0b498d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/94000000/93500000/93497900/93497853/ed872576.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 reviews)

"My husband and I were looking for a quiet place to spend a weekend and Jake and Hannah’s place was perfect! We were close to restaurants, farmers market, arts and crafts fair! The house was clean, had everything we needed. The jacuzzi and the fire pit were perfect for the cool nights. Check in was easy, and Jake and Hannah were prompt to answer any questions. We would love stay again! Thank you for sharing your house! "

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

Kristina P.

[](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)

![Dining](https://images.trvl-media.com/lodging/110000000/109560000/109551000/109550902/w3072h2045x0y1-67f7484c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109560000/109551000/109550902/w3072h2045x0y1-72e8894b.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)

### 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 reviews)

"Great cabin with lots of room. Secluded on a country road but very close to town. We had a wonderful stay. "

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

Mark R.

[](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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115080000/115079500/115079418/9a46cd25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115079500/115079418/ba7c3471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115080000/115079500/115079418/59a6d7cf.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 | In-room dining](https://images.trvl-media.com/lodging/45000000/44920000/44910100/44910019/dce584d6.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)

![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)

### 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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-14&endDate=2026-02-15&regionId=553248635976432508&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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Cottages

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Aparthotels

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Private vacation homes

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Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America&regionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=CHALET)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America&regionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=CONDO)

Apartments

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Villas

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## Top Windsor County Hotel Reviews

![Comfort Inn White River Junction](https://images.trvl-media.com/lodging/1000000/10000/8900/8850/a720acb3_y.jpg)

### Comfort Inn White River Junction

10/10 Excellent

"Very nice staff, clean rooms. "

[](https://expedia.ca/White-River-Junction-Hotels-Comfort-Inn.h8850.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 Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg)

### The Shire Woodstock

10/10 Excellent

"Love the shire !"

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

![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg)

### Align Inn Vermont

10/10 Excellent

"Very polite staff and very clean rooms."

[](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.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)

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

### COHO Inn & Motor Lodge

10/10 Excellent

"The room was so comfortable and the staff here is top notch. The included breakfast is one of the best I’ve ever had when it was included with your stay. This place is a hidden jewel!"

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

"Wonderful as always! "

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

![Norwich Inn](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519573/30ba8066_y.jpg)

### Norwich Inn

10/10 Excellent

"Spectacular place and great service !! "

[](https://expedia.ca/Norwich-Hotels-Norwich-Inn.h2519573.Hotel-Information)

![The Quechee Inn at Marshland Farm](https://images.trvl-media.com/lodging/2000000/1930000/1924800/1924710/c8372335_y.jpg)

### The Quechee Inn at Marshland Farm

10/10 Excellent

"Had a great Stay. Food was Very Good"

[](https://expedia.ca/Quechee-Hotels-The-Quechee-Inn-At-Marshland-Farm.h1924710.Hotel-Information)

## Find out more about Windsor County

## Windsor County Chalets information

| Number of reviews | 578        |
| ----------------- | ---------- |
| Accommodation     | 23 Chalets |
| Lowest Price      | CA $718    |
| Highest Price     | CA $906    |

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- [Lake Hotels in Woodstock ](https://www.expedia.ca/Woodstock-Hotels-Lake-Hotels.0-0-d10868-tLakeHotels.Travel-Guide-Filter-Hotels)
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- [Flights to Quechee ](https://www.expedia.ca/Cheap-Flights-To-Quechee.d9580.Travel-Guide-Flights)
- [Flights from Woodstock ](https://www.expedia.ca/lp/flights/10868/flights-from-woodstock)

- [Billings Farm and Museum ](https://www.expedia.ca/Billings-Farm-And-Museum-Woodstock.d6175222.Vacation-Attraction)
- [Quechee Gorge Bridge ](https://www.expedia.ca/Quechee-Gorge-Bridge-White-River-Junction.d6139298.Vacation-Attraction)
- [Quechee Ski Hill ](https://www.expedia.ca/Quechee-Ski-Hill-White-River-Junction.d6175207.Vacation-Attraction)
- [Visit Quechee ](https://www.expedia.ca/Quechee.dx9580)
- [Visit South Woodstock ](https://www.expedia.ca/South-Woodstock.dx6149659)
- [Woodstock Vacations ](https://www.expedia.ca/Woodstock.d10868.Destination-Travel-Guides)
- [Visit Woodstock ](https://www.expedia.ca/Woodstock.dx10868)

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- [Quechee Vacation Rentals ](https://www.expedia.ca/Quechee-Vacation-Rentals.d9580.Travel-Guide-VacationRentals)

- [Things to do in Woodstock ](https://www.expedia.ca/Things-To-Do-In-Woodstock.d10868.Travel-Guide-Activities)

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