
Chalet holiday rentals in Woodstock
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Woodstock
Guests agree: These chalets are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Woodstock chalet rentals
Family-friendly chalet rentals

Windham Immaculate Ski Chalet w / Awesome Fire Pit

Modern Chalet with Hot Tub and Lake Access

Riverfront Ski Chalet

Black Forest Haus | Cozy • Authentic • Whimsical

Gorgeous Chalet with Lots of Room!

Welcome to the Shangri-La Chalet!

Vintage 70s Ski Chalet- minutes from Ski slopes!

Modern Chalet w/Outdoor TV & Covered HOT TUB+POOL
Luxury chalet rentals

Blue Spruce Chalet — Hot Tub, Pet Friendly

Daydream Mountain Art-Chateau | Hot Tub & Pool

Chalet w Views Firepit 2 Grills Deck Fast WiFi

Voted BEST Vacation Rental > Hot Tub + the Gunks

Secluded Catskills Designer Lodge - Windham/Hunter

Traveler’s Dream! Sunset Views, Hiking, King Beds!

Beautiful Windham Ski/Summer House

White Holiday Cozy Chalet Pool/Hot Tub/bubble room
Lakefront chalet rentals

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

Large & Sunny Lakefront Home-kayaks/fire pit/games

Waterfront Lake Home, close to Hunter & Windham

Eagles' retreat

Brand New Lakefront Retreat! Kayaks/Firepit/Games

Maple Lodge - Luxury Cabin

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

Lakefront Chalet-Spacious | Dock-Kayaks |Guest Fav
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Rentals with outdoor seating Woodstock
- Rentals with a hot tub Woodstock
- Cabin rentals Woodstock
- Pet-friendly rentals Woodstock
- Cottage rentals Woodstock
- Waterfront rentals Woodstock
- House rentals Woodstock
- Rentals with an EV charger Woodstock
- Fitness-friendly rentals Woodstock
- Rentals with a fire pit Woodstock
- Family-friendly rentals Woodstock
- Rentals with a patio Woodstock
- Rentals with pools Woodstock
- Condo rentals Woodstock
- Apartment rentals Woodstock
- Rentals with breakfast Woodstock
- Rentals with a washing machine and dryer Woodstock
- Rentals with a fireplace Woodstock
- Chalet rentals Ulster County
- Chalet rentals New York
- Chalet rentals United States
- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Howe Caverns
- The Kartrite Resort & Indoor Waterpark
- John Boyd Thacher State Park
- Resorts World Catskills
- Bash Bish Falls State Park
- Zoom Flume
- Hudson Highlands State Park
- Walkway Over the Hudson State Historic Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Catamount Mountain Ski Resort
- Norman Rockwell Museum
- Windham Mountain
- Taconic State Park
- Villa Roma Ski Resort
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Plattekill Mountain