
Cottage vacation rentals in Windham
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Top-rated cottage rentals in Windham
Guests agree: these cottages 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 Windham cottage rentals
Cottage rentals with a hot tub

Charming Cottage in Kingston - License #002740

Charming Mtn Stay | Views, Hot Tub, Prime Location

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

Hits Adjacent | Pet Friendly | Caraway Cottage

Tranquil Cottage in Catskill/Roxbury w/ Hot tub

Pet-Friendly Hudson Escape w/ Hot Tub

Country Cottage w/ HOT TUB & Views

40 acre woods: A Catskills home in a National Park
Pet-friendly cottage rentals

Woodstock Dog friendly Cottage in Town; large yard

Cozy Catskills Cottage with Mountain Views

Woodstock Mountain Cottage w/ Pool

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

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

Cottage w Pond Pet Friendly | Near Attractions

Swan Cottage with Expansive Hudson River Views

Whimsical Woodland Cottage in Stone Ridge NY
Private cottage rentals

Catskills Stream-side Home Hike & Relax

Creekside Cottage

Kinderhook Lakefront Retreat-private, kayaks, ac

Hidden Gem Cottage — cozy escape to play or WFH

Carriage House on Falls, Walk to Village

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm

Hidden Pines - Downtown Woodstock by Millstream!

Woodstock Streamside Cottage
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- Hunter Mountain
- Minnewaska State Park Preserve
- Glimmerglass State Park
- Belleayre Mountain Ski Center
- The Kartrite Resort & Indoor Waterpark
- Howe Caverns
- John Boyd Thacher State Park
- Resorts World Catskills
- Taconic State Park
- Albany Center Gallery
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Catamount Mountain Ski Resort
- Windham Mountain
- Hancock Shaker Village
- Opus 40
- Pineridge Cross Country Ski Area
- Naumkeag
- Hunter Mountain Resort
- Butternut Ski Area and Tubing Center
- Peebles Island State Park
- Berkshire Botanical Garden