
House vacation rentals in Chatham
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Top-rated house rentals in Chatham
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chatham house rentals
House rentals with a pool

Private lakefront home, hot tub & resort amenities

midcentury mod * HOT TUB * walk out trail 2 mohonk

4Br Mountain Brook House on 130 acres w/ trails

Woodstock Retreat- Heated Pool/Hot Tub/FirePit

Upstate Modern Scandinavian Barn in the Catskills

Red Rock Summit: Mtn Escape w/ Pool, Pond + Views

Sunbeam Lodge: Pool+Hot Tub, 50 Acres, ‘70s Oasis

Curl Up & Relax - Cozy Stylish Stay nr Woodstock
Weekly house rentals

Renovated Country Retreat by Evergreen Home

Luxury retreat with sauna on 20 acres

Cozy Chatham Retreat

The Red House

Private Home in The Berkshires (New Hot Tub!)

Cozy Country Cape House | Close to Hudson

Chatham Country Getaway

Cozy Lakeside Retreat
Private house rentals

Hawthorne Valley Barn

Haddock + Cotter - Chic Farmhouse and Barn w/ Pool

Fiddlehead Lodge: Upstate NY Stay near Berkshires

Majestic lake front house

Vibing Hudson Retreat | Pet-Friendly w/ Hot Tub

Chic Hudson Farmhouse w/ Fireplace & Porch

Little Ghent Manor

Farmhouse Retreat, Outdoor Dining/Fire-Pit & Golf
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- South Jersey Vacation rentals
- Hunter Mountain
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Belleayre Mountain Ski Center
- Berkshire East Mountain Resort
- Howe Caverns
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Saratoga Spa State Park
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Windham Mountain
- Taconic State Park
- Mount Tom State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Albany Center Gallery
- Hunter Mountain Resort
- Bousquet Mountain Ski Area