Compare Windham Cottage Rentals

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Featured Cottages in Windham

Streamside Cottage Half Mile to Town of Woodstock

$284 nightly

$318 total

Sep 7 - Sep 8

Total with taxes and fees

Guests staying at this cottage have access to a garden and barbecue grills.

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Guests staying at this cottage have access to a garden and barbecue grills.

The Cabin at Chichester in the Catskills Mountains

Guests staying at this cottage have access to barbecue grills and a garden.

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Woodsy Country Cottage, HITS Horse Show, Fall Foliage, Skiing, Hunter Mt, Hiking

Guests staying at this cottage have access to a garden and barbecue grills.

Country Cottage with beautiful views and easy access to Catskills activities.

Guests staying at this cottage have access to a garden and barbecue grills.

Charming Cottage in Private Lake Community (Pet-Friendly!)

At this cottage, guests have access to a gym, laundry facilities, and barbecue grills. This cottage also has a garden.

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.

Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

This cottage features a hot tub and barbecue grills. This smoke-free cottage also has a garden.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Windham

Wylder Hotel Windham

19 New York 296 Windham NY

$327 total

per night

Aug 26 - Aug 27

8.8/10 Excellent! (118 reviews)

Hotel Vienna

107 State Route 296 Windham NY

$157 total

per night

Aug 23 - Aug 24

9.4/10 Exceptional! (848 reviews)

Eastwind Windham

5088 NY-23 Windham NY

$246 total

per night

Aug 25 - Aug 26

9.2/10 Wonderful! (115 reviews)

Cottages

Book a cottage in Windham
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Windham. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Windham better.

Cottage apartments in Windham range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Windham
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Windham and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Windham cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Windham. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Windham Cottages essential information

Accommodation	186 Cottages
Lowest Price	$157
Highest Price	$327
Popular accommodation	Streamside Cottage Half Mile to Town of Woodstock, Junebug Cottage: peace, love and privacy a short walk to Woodstock village green, The Cabin at Chichester in the Catskills Mountains, Charming Artist's Retreat, Woodsy Country Cottage, HITS Horse Show, Fall Foliage, Skiing, Hunter Mt, Hiking, Country Cottage with beautiful views and easy access to Catskills activities., Charming Cottage in Private Lake Community (Pet-Friendly!), ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!