Top Chalets in Windsor County from $514

Windsor County Chalets
Vermont
United States of America
Chalets
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A red convertible car parked in front of a brick house with black shutters and a white picket fence.

Our top choices for Windsor County chalets

A two-story house with a steeply pitched roof, surrounded by snow-covered ground and trees.

A living room with a sectional sofa, a coffee table, and a kitchen in the background.

A living room with a sectional sofa, a fireplace, and a wall-mounted TV.

A dining area with a rectangular table and six chairs.

1. Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

Ludlow

9.6 out of 10, Exceptional, (39 reviews)

9.6/10

Exceptional

(39 reviews)

"Great location for a family of five to enjoy a ski trip!"

Jason B.

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

A wooden deck with four Adirondack chairs and a small table.

A kitchen with red cabinets, a granite countertop, and a coffee maker.

A spacious living room with a large couch, a coffee table, and a fireplace. There are multiple windows providing natural light and a view of the outdoors.

A cabin with a balcony, surrounded by trees and snow.

2. Okemo Mountain Chalet W/ Hot Tub and Game Room

Okemo Mountain Chalet W/ Hot Tub and Game Room

Ludlow

9.8 out of 10, Exceptional, (165 reviews)

9.8/10

Exceptional

(165 reviews)

"Place was great, and well kept. Kitchen was fully stocked and we had a great time. Bob provides very detailed instructions."

David T.

Okemo Mountain Chalet W/ Hot Tub and Game Room

A two-story house with a covered porch, outdoor seating, and string lights.

A two-story house with a red roof, a porch with string lights, and a wreath on the front door.

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

A long wooden dining table with chairs, a central floral arrangement, and a hanging light fixture.

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

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

Woodstock

10.0 out of 10, Exceptional, (29 reviews)

10/10

Exceptional

(29 reviews)

"Great space for large family gathering! "

ted d.

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

A hot tub on a wooden deck with a view of a forest and a lake.

A cozy living room with a fireplace, wooden ceiling, and a large window.

A wooden cabin with a green roof, a covered porch, and a fenced yard.

A bunk bed room with a fan, a window, and wooden walls.

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

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

Chester

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

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

Mark R.

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

A two-story wooden cabin with a balcony, surrounded by autumn foliage.

A wooden cabin interior with a dining table, chairs, and a kitchen area with a window overlooking a deck.

A cozy room with a stone fireplace, wooden walls, a sofa, a small table, and a pool table.

A wooden deck with green lounge chairs and a fire pit.

5. Okemoskichalet with Game Room & Hot Tub on Okemo Mt. 1 mile to base! Sleeps 12

Okemoskichalet with Game Room & Hot Tub on Okemo Mt. 1 mile to base! Sleeps 12

Ludlow

9.8 out of 10, Exceptional, (133 reviews)

9.8/10

Exceptional

(133 reviews)

"We had a great stay. Close to the ski slope! Loved the wood stove after a day of skiing. Made the house cozy and warm. "

Julianne M.

Okemoskichalet with Game Room & Hot Tub on Okemo Mt. 1 mile to base! Sleeps 12

A wooden deck with a bench, overlooking a grassy area with tall trees and distant mountains.

A spacious living room with a stone fireplace, a flat-screen TV mounted above it, and a wooden dining area with bar stools.

A spacious living room with a large L-shaped leather sofa, a wooden coffee table, and a patterned rug.

A two-story wooden cabin with a balcony, a large window, and a porch area.

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

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

Ludlow

10.0 out of 10, Exceptional, (48 reviews)

10/10

Exceptional

(48 reviews)

"Great communication, very nice place and close to the mountain "

Craig L.

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

A snow-covered landscape with a red building surrounded by trees.

A kitchen with a stove, oven, and a large island with a kettle. There is a wooden staircase and a dining area with chairs and a table.

A cozy living room with a fireplace, leather sofas, and large windows.

A cozy cabin interior with wooden walls, a fireplace, leather sofas, and a large window offering a view of the forest.

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

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

ludlow

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 reviews)

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

Anna B.

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

A deck with a table and chairs, an umbrella, and a view of a forest.

A wooden interior with a large stained glass window, a glass shower enclosure, and a wooden vanity with two sinks and a mirror.

A bedroom with a bed, wooden walls, a ceiling fan, a window with curtains, a door, a small cabinet, and a framed picture on the wall.

A wooden cabin with a snow-covered roof, a white door, and a small porch area.

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

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

Woodstock

10.0 out of 10, Exceptional, (75 reviews)

10/10

Exceptional

(75 reviews)

"Loved the location, house and all it encompassed. Kat was super responsive! If we come back, love to stay here again!"

Cindy A.

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

A wooden hot tub on a deck with snow-covered railings and trees in the background.

A modern kitchen with a fireplace, wooden flooring, and a dining area with chairs and a table.

A spacious living room with a high ceiling, a fireplace, a large window, and a cozy seating area.

A snow-covered cabin with a large window and a porch, surrounded by a forested area.

9. "The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Plymouth

9.8 out of 10, Exceptional, (37 reviews)

9.8/10

Exceptional

(37 reviews)

"We very much enjoyed our stay and the property is in excellent proximity to Killington/Pico."

Ross D.

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

A cabin surrounded by dense forest with autumn foliage.

A basket containing a variety of food items including a bag of Buttermilk, a package of Bigfoot Chalet, and other snacks.

A house with a wooden deck, two wooden chairs, a door, and a wreath.

10. Escape to Your Own Private Vermont Retreat

Escape to Your Own Private Vermont Retreat

Plymouth

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

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

Ed N.

Escape to Your Own Private Vermont Retreat

A two-story white house with a balcony, surrounded by snow.

A modern living room with a sectional sofa, a coffee table, and a TV mounted on the wall.

A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

A bedroom with a fireplace, a bed, a television, and a ceiling with wooden beams.

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

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

Ludlow

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Great location to the slopes!Comfortable house layout for a multiple families.Nice kitchen too."

Kim H.

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

A rustic wooden cabin with a steeply pitched roof, a wooden staircase leading to a deck, and surrounded by lush greenery.

A cozy cabin interior with a wooden interior, a cushioned sofa, a small table with a lamp, and a window with a view of trees.

A cozy attic bedroom with a sloped ceiling, a bed with blue and purple bedding, and a stained glass window with floral patterns.

A cozy cabin interior with a wooden staircase, a sofa with patterned cushions, a bookshelf, and a potted plant.

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

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

Stockbridge

9.6 out of 10, Exceptional, (54 reviews)

9.6/10

Exceptional

(54 reviews)

"Great stay! House was awesome and host was responsive"

Brendan H.

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

A wooden building with large windows and a covered porch.

A modern bathroom with a glass shower, wooden ceiling beams, and a small window.

A wooden cabin with a snow-covered roof and a balcony, surrounded by trees and snow.

A cozy cabin interior with a wooden interior, a mounted television, a sofa, and a window overlooking a snowy landscape.

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

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

Ludlow

9.4 out of 10, Exceptional, (27 reviews)

9.4/10

Exceptional

(27 reviews)

"Great location and very comfortable house. Loved the multiple fireplaces! "

Marissa F.

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

A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

A wooden deck with a table, chairs, a bottle of wine, and a glass.

A spacious living room with a large sliding glass door leading to a balcony, a cozy sofa, a coffee table, and a television.

A cozy living room with a stone fireplace, a large sliding glass door leading to a deck, and a television mounted on the wall.

14. Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

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

Gerald S.

$487 nightly

The price is $514

$514 total

Oct 27 - Oct 28

Total with taxes and fees

Gnome Home Mountain Ski Chalet w/Sauna Killington

A two-story house with a blue exterior, a porch with white railings, and a large flowering bush in the foreground.

A kitchen with white cabinets, a black refrigerator, a microwave, a stove, and a sink. There are two white chairs at the island.

A wooden interior with a dining area, kitchen, and staircase.

A room with a black dresser, a television on the wall, a potted plant, a framed photo, and folded towels.

15. Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

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

Chester

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"We had a great stay. The house had the perfect amenities for our family ski weekend. Hoping we can come again! "

Hilary S.

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

A dark wooden door with a welcome mat, two lit Christmas trees, and a ceiling light.

A cozy cabin interior with a fireplace, wooden beams, a couch, and a coffee table.

A cozy room with a wooden ceiling, large windows, a sofa, a dining table, and a kitchen area.

A spacious room with a large wooden dining table, multiple chairs, a sofa, and a view of autumn trees through large windows.

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

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

Plymouth

9.8 out of 10, Exceptional, (31 reviews)

9.8/10

Exceptional

(31 reviews)

"Wonderful place to stay, perfect ski vacation for me & my family "

Charles M.

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

A wooden deck with outdoor furniture, a grill, and a staircase leading to an upper level.

A kitchen with a central island, wooden ceiling, and pendant lighting.

A spacious living room with a high ceiling, large windows, a wooden coffee table, and a sofa set.

A cozy living room with a fireplace, wooden ceiling, and large windows.

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

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

Cavendish

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"Exceptional spot for a family getaway - close proximity to Okemo Mountain. The home is beautifully designed, spotlessly clean and the hosts thought of everything to make it a comfortable and inviting stay. Highly recommend! "

Elizabeth M.

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

A two-story cabin with a balcony, surrounded by a forest.

A modern living room with a sectional sofa, a round coffee table, and a lamp on a side table.

A compact, stainless steel laundry room with two large front-loading washing machines.

An aerial view of a house surrounded by dense forest, with a visible driveway and a small lawn area.

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

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

Chester

9.4 out of 10, Exceptional, (6 reviews)

9.4/10

Exceptional

(6 reviews)

"Greay family trip. Comfortable house with great hot tub and fire pit."

Victoria H.

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

A wooden cabin with a large porch and a covered outdoor seating area.

A spacious kitchen with modern appliances and a dining area with a sofa and tables.

A spacious loft-style room with a large dining table, a sofa, and a ceiling fan.

A spacious kitchen with a large island, wooden beams, and large windows offering views of the outdoors.

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

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

Plymouth

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

A wooden cabin with a large window, a chimney, and a deck.

A modern kitchen with wooden cabinets, a dining area with a table and chairs, and a view of trees through large windows.

A wooden cabin with a deck, a large window, and string lights.

A staircase leading to a wooden deck, a large potted plant by a glass door, and a view of greenery outside.

20. Scandinavian design Chalet with private hiking trail and Goodland hot tub

Scandinavian design Chalet with private hiking trail and Goodland hot tub

Royalton

Scandinavian design Chalet with private hiking trail and Goodland hot tub

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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Top Windsor County Hotel Reviews

Align Inn Vermont

8/10 Good

"Room was clean, staff was friendly and helpful, breakfast was satisfying, pool was clean and refreshing. All was very good. Except...be careful if you have a room on the street side as it is very loud."

Greg 2-night trip

Posted 7 hours ago

Align Inn Vermont

The Hartness House

10/10 Excellent

"Excellent hotel. Perfect position for the road trip we were on. The only thing that wasn’t explained to us was how we had to pay."

Christine 1-night trip

Posted 9 hours ago

The Hartness House

The Shire Woodstock

10/10 Excellent

"Great views"

J R 4-night trip

Posted 15 hours ago

The Shire Woodstock

Fullerton Inn

8/10 Good

"Staff was very friendly. It was quiet. Location was perfect if you want to be located in a small quaint picturesque town. Charming."

Lisa 2-night trip

Posted 17 hours ago

Fullerton Inn

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"Nice hot tubs"

David 3-night trip

Posted 1 day ago

Jackson Gore Village, A Vail Resorts Property

Sleep Woodstock Motel

10/10 Excellent

"This place is amazing! Keyless check-in and entry was a breeze. Will stay again. Loved it!"

patricia 2-night trip

Posted 1 day ago

Sleep Woodstock Motel

Lincoln Inn & Gallery

8/10 Good

"Beautiful property! Our room was clean and beautiful! Wasn’t crazy about the room overlooking the road and not having dinner or bfast at the resort. Staff was very nice and super accommodating!!!! The hot chocolate bar is a major plus"

Asoudeh Hadi 1-night trip

Posted 3 days ago

Lincoln Inn & Gallery

Woodstock Inn & Resort

10/10 Excellent

"Wonderful inn! Everything was wonderful: rooms, food, etc!!"

Ann 2-night trip

Posted 3 days ago

Woodstock Inn & Resort

Pointe at Castle Hill Resort

10/10 Excellent

"Very nice stay and nice rooms."

Nicole 1-night trip

Posted 4 days ago

Pointe at Castle Hill Resort

Find out more about Windsor County

Windsor County Chalets information

Number of reviews	677
Accommodation	27 Chalets
Lowest Price	$514
Highest Price	$514

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Find Chalets in Windsor County, VT from $514

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Top Cities in Windsor County

Woodstock

Our top choices for Windsor County chalets

1. Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

2. Okemo Mountain Chalet W/ Hot Tub and Game Room

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

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

5. Okemoskichalet with Game Room & Hot Tub on Okemo Mt. 1 mile to base! Sleeps 12

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

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

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

9. "The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

10. Escape to Your Own Private Vermont Retreat

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

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

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

14. Gnome Home Mountain Ski Chalet w/Sauna Killington

15. Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

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

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

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

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

20. Scandinavian design Chalet with private hiking trail and Goodland hot tub

Find vacation rentals that suit your style

Top Windsor County Hotel Reviews

Align Inn Vermont

Find out more about Windsor County

Windsor County Chalets information

Explore a world of travel with Expedia