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Chalets in Windsor County

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Top Cities in Windsor County

A red convertible car parked in front of a brick house with black shutters and a white picket fence.
ChaletsChalets

Woodstock

Woodstock

Our top choices for Windsor County chalets

Exterior

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)
"Great location for a family of five to enjoy a ski trip!"
United States
Jason B.
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Outdoor spa tub

2. 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)
"Great cabin with lots of room. Secluded on a country road but very close to town. We had a wonderful stay. "
United States
Mark R.
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Exterior

3. 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)
"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. "
United States
Julianne M.
Okemoskichalet with Game Room & Hot Tub on Okemo Mt. 1 mile to base! Sleeps 12
Exterior

4. 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)
"Location was perfect, drops you right on the Sachem run. The house was welcoming and fantastic for our large group of multiple families, and the host was helpful and available for any questions. It was a great stay and would love to stay again!"
United States
Wendy N.
Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults
Outdoor spa tub

5. "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)
"We very much enjoyed our stay and the property is in excellent proximity to Killington/Pico."
United States
Ross D.
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Outdoor dining

6. 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)
"Wonderful spot -- loved using the sauna! Owners extraordinarily responsive on any question and issue. If you are looking for a quiet, expansive and uniquely comfortable space in this part of the world, this is the one!"
United States
Brian R.
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Exterior

7. 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, (28 reviews)
"Great space for large family gathering! "
United States
ted d.
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Property grounds

8. 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)
"Great communication, very nice place and close to the mountain "
United States
Craig L.
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Exterior

9. 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)
"Great stay! House was awesome and host was responsive"
United States
Brendan H.
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Exterior

10. Escape to Your Own Private Vermont Retreat

Escape to Your Own Private Vermont Retreat
Plymouth
10.0 out of 10, Exceptional, (16 reviews)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
Escape to Your Own Private Vermont Retreat
Outdoor spa tub

11. 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)
"Great location and very comfortable house. Loved the multiple fireplaces! "
United States
Marissa F.
Okemo Hideaway – Secluded Woodland Chalet 7 minutes to Slopes & Village
Exterior

12. 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)
"Great location to the slopes!Comfortable house layout for a multiple families.Nice kitchen too."
United States
Kim H.
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
Exterior

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

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester
10.0 out of 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! "
United States
Hilary S.
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Exterior detail

14. 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)
"Wonderful place to stay, perfect ski vacation for me & my family "
United States
Charles M.
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Terrace/patio

15. 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)
"Place was great, and well kept. Kitchen was fully stocked and we had a great time. Bob provides very detailed instructions."
United States
David T.
Okemo Mountain Chalet W/ Hot Tub and Game Room
Terrace/patio

16. 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)
"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! "
United States
Elizabeth M.
Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow
Exterior

17. 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)
"Greay family trip. Comfortable house with great hot tub and fire pit."
United States
Victoria H.
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
Property grounds

18. 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)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is AED 800
AED 1,853 total
includes taxes & fees
30 Aug - 31 Aug
Gnome Home Mountain Ski Chalet w/Sauna Killington
Exterior

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
Property grounds

20. Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway

Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
Woodstock
The price is AED 909
AED 1,602 total
includes taxes & fees
29 Aug - 30 Aug
Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
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

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Good location near everything you need rooms have river views"
Paul 1-night trip
Posted 2 hours ago
The Shire Woodstock

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