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Windsor Chalets

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Chalets in Windsor

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (15)
"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
$414 nightly
The price is $464
Sep 29 - Sep 30
Total with taxes and fees
Cozy Creekside Chalet centrally located near 4 ski resorts

Killington Chalet - Great Space and Location!

9.6 out of 10, Exceptional, (15)
"Our group of 10 friends had a wonderful stay at the Chalet. Great location to the mountain and local restaurants and entertainment. Plenty of room to spread out and great communal area as well. "
Killington Chalet - Great Space and Location!

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

10.0 out of 10, Exceptional, (5)
"Girls family weekend, relaxing, visiting and enjoying the hot tub."
Spacious 5-bedroom chalet with AC and WiFi in charming Chester

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

10.0 out of 10, Exceptional, (25)
"This property is very charming and located in an ideal spot to get around the area easily. We had a wonderful time playing games, doing puzzles, sitting in the hot tub, and exploring the river."
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

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

9.8 out of 10, Exceptional, (127)
"We found the hosts to be super helpful and friendly. Location was fantastic. We loved the hot tub and wood burning stove. It was a perfect stay for my extended family and I. The beds were also super comfortable-we slept great! We would definitely recommend this spot!"
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.

2.0 star property
8.0 out of 10, Very Good, (1)
"It was easy to check in and out and there was plenty of parking. There were also ACs in all of the bedrooms but 1. This was important since it was 90 degrees. We only wish the ice machine that was provided worked. The living room furniture, especially the couch, was amazingly comfy. We did a lot of bonding in that space. When we walked in on the first evening, there were some windows open, and there was a furry chicken nugget sitting on the arm of a chair though. The basement had bedrooms in...
$1,021 nightly
The price is $1,154
Sep 29 - Sep 30
Total with taxes and fees
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.

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

9.8 out of 10, Exceptional, (35)
"Had a lovely weekend with "
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Okemo Mountain Chalet W/ Hot Tub and Game Room

9.8 out of 10, Exceptional, (161)
"This was our second time staying at the Bear Chalet and we absolutely loved it. So much space for multiple families and very kid friendly!"
Okemo Mountain Chalet W/ Hot Tub and Game Room

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

10.0 out of 10, Exceptional, (27)
"A terrific place. Highly recommended. We had a great family ski vacation."
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

South View Chalet!

9.2 out of 10, Wonderful, (27)
"Great location and house. Perfect for large groups, there is plenty of space with multiple rooms so your group can spread out. Minutes to Killington mountain. "
South View Chalet!

Mountain View Chalet Fabulous views from the hot tub with large entertaining area just off Killington Road

10.0 out of 10, Exceptional, (1)
Mountain View Chalet Fabulous views from the hot tub with large entertaining area just off Killington Road

4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

9.8 out of 10, Exceptional, (18)
"Beautiful place "
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

Fall into Cozy at Bigfoot Chalet

2.0 star property
10.0 out of 10, Exceptional, (13)
"We only stayed on night while exploring the area, but it was so lovely! The more we looked, the more cute, and thoughtful elements we sae. Would definitely come back!"
$404 nightly
The price is $453
Sep 30 - Oct 1
Total with taxes and fees
Fall into Cozy at Bigfoot Chalet

Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities

10.0 out of 10, Exceptional, (107)
"The house was equipped with everything we needed! Cant wait to come back! "
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities

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

9.6 out of 10, Exceptional, (49)
"Loved a ll of it. Comfortable quiet and su c h a relaxing place. Would definetly rentvthis place again. TY Janie it was do nice"
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

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

10.0 out of 10, Exceptional, (10)
"Great house, made our ski weekend easy and fun. House is better than the pictures."
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

Okemo 6 Bedroom Chalet.

9.4 out of 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. "
Okemo 6 Bedroom Chalet.

Modern Chalet by Mt. Sunapee

Modern Chalet by Mt. Sunapee

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

10.0 out of 10, Exceptional, (69)
"This was a memorable and fun filled trip. The falcon house chalet is lovely. You can tell the things inside were carefully curated, and the surrounding woods, Finnish sauna, babbling brook made it so comfortable, we didn't want to leave. We made good use of the bikes and enjoyed many activities nearby. We highly recommend falcon house for a chill Vermont vacation. Kat, the host was lovely, made sure we had all we needed and she was in contact via text in case we had questions. "
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni

9.8 out of 10, Exceptional, (59)
"We stayed along with 2 other families while in time visiting Okemo mountain. The house was very welcoming, clean and exactly how the picture showed it. We would stay here again next time we were in time. "
Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni
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 Hotel Reviews

Find out more about Windsor

Find out more about Windsor

Windsor Chalets information

Number of reviews
667
Accommodation
51 Chalets
Lowest Price
$453
Highest Price
$1,154

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