
Cottage holiday rentals in Chatham
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Top-rated cottage rentals in Chatham
Guests agree: These cottages 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 Chatham cottage rentals
Cottage rentals with a hot tub

Waterfront 3 Bdrm. w/ Hot Tub & Outdoor Fire Pit!

Couples Getaway, Hot Tub, 3 acres, 5mi to Kingston

Hits Adjacent | Pet Friendly | Caraway Cottage

Pet-Friendly Hudson Escape w/ Hot Tub

Hot Tub & Chic Catskills Woodstock Design Retreat

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl

Stream Come True | Hot Tub, Ski, Hike, Relax

Woodstock Carriage House HotTub FirePit Pool
Pet-friendly cottage rentals

Flat Rocks Cottage: Ski and Swim in the Catskills!

Hudson Valley Cottage

Charming creekside cottage in Phoenicia

Kapitan’s Cottage: Private Retreat with Salt Pool

Beautifully Nestled Berkshires Home

The Kaaterskill Cottage - views of Hunter Mtn!

Magnolia Cottage

Newly Built Cottage in Housatonic Valley
Private cottage rentals

Direct streamside with private stream access

Stunning Woodstock 1 BR Hideaway

Creekfront Cottage between Phoenicia & Hunter Mtn.

Mountain views, mid-century style! 1 mile to town.

Cottage on the creek with wonderful waterfall view

Cozy Catskill Cottage on the Pantherkill

Beautiful cottage at the foot of the Birkshires

Garden Cottage In The Catskills
Destinations to explore
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- Hunter Mountain
- Saratoga Race Course
- Belleayre Mountain Ski Center
- Howe Caverns
- John Boyd Thacher State Park
- Taconic State Park
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Zoom Flume
- Bash Bish Falls State Park
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Saratoga Spa State Park
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Catamount Mountain Ski Resort
- Windham Mountain
- Mohawk Mountain Ski Area
- Albany Center Gallery
- Beartown State Forest
- Opus 40
- Bousquet Mountain Ski Area
- Hancock Shaker Village
- Northern Cross Vineyard