Chester chalets
We found 61 chalets — enter your dates for availability
Explore Chester chalet rentals
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Sleeps 8 · 5 bedrooms · 2+ bathrooms
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
Sleeps 6 · 2 bedrooms · 2 bathrooms
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Sleeps 8 · 4 bedrooms · 1+ bathroom
Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults
Sleeps 22 · 8 bedrooms · 3+ bathrooms
Autumn Escape - Chalet Retreat in the Heart of the Mountains. Dog friendly!
Sleeps 5 · 2 bedrooms · 1 bathroom
Minutes from Stratton Mountain for Less Money
Sleeps 6 · 3 bedrooms · 1+ bathroom
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