Compare Windham Cottage Rentals

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Featured Windham Cottages

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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

    Hotel Vienna

    Hotel Vienna

    107 State Route 296, Windham, NY
    The price is $139 per night from May 22 to May 23
    $139
    includes taxes & fees
    $129 per night
    May 22 - May 23
    9.2/10 Wonderful! (555 reviews)
    Eastwind Windham

    Eastwind Windham

    5088 NY-23, Windham, NY
    The price is $214 per night from May 2 to May 3
    $214
    includes taxes & fees
    $199 per night
    May 2 - May 3
    9.2/10 Wonderful! (52 reviews)
    Wylder Hotel Windham

    Wylder Hotel Windham

    19 New York 296, Windham, NY
    The price is $235 per night from May 5 to May 6
    $235
    includes taxes & fees
    $217 per night
    May 5 - May 6
    8.2/10 Very Good! (54 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
190 Cottages
Lowest Price
$139
Highest Price
$310
Popular accommodation
Streamside Cottage Half Mile to Town of Woodstock, Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!, TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too, Romantic cottage w/hot tub . Close to skiing and breweries . Pet friendly! , ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, Junebug Cottage: peace, love and privacy a short walk to Woodstock village green, Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream, The Cabin at Chichester in the Catskills Mountains, NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!