Compare Windham Cottage Rentals

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Featured Windham Cottages

Streamside Cottage Half Mile to Town of Woodstock

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

Kitchen

Free WiFi

Experience Peace in this Cozy country cottage nestled beneath the mountains

$286 nightly

$309 total

Jan 25 - Jan 26

Total with taxes and fees

This cottage offers a water park, laundry facilities, and local meal delivery service. Transportation is made easy with limo/town car service. Other amenities at this family-friendly cottage include a living plant wall, barbecue grills, and a garden.

Kitchen

Washer

Dual-Dwelling Catskill Getaway Near Belleayre & Plattekill

At this cottage, guests have access to features like laundry facilities. This family-friendly cottage also has a garden.

Kitchen

Washer

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

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

Kitchen

Washer

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

$173 nightly

$193 total

Jan 24 - Jan 25

Total with taxes and fees

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

Pet friendly

Free WiFi

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.

Kitchen

Free WiFi

Little red house just outside of Woodstock

$500 nightly

$559 total

Jan 25 - Jan 26

Total with taxes and fees

At this cottage, guests have access to features like laundry facilities.

Washer

Dryer

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

Kitchen

Washer

Private Home ~ All Yours ~ In town ~ fenced in yard ~ Pets welcome!

Guests of this cottage enjoy features like a gym, a hot tub, and an arcade/game room. Other amenities at this family-friendly cottage include laundry facilities, a garden, and barbecue grills.

Hot Tub

Kitchen

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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

107 State Route 296 Windham NY

$149 nightly

$161 total

Feb 22 - Feb 23

Total with taxes and fees

9.2/10 Wonderful! (745 reviews)

Wylder Hotel Windham

19 New York 296 Windham NY

$252 nightly

$273 total

Jan 25 - Jan 26

Total with taxes and fees

8.6/10 Excellent! (92 reviews)

Eastwind Windham

5088 NY-23 Windham NY

$233 nightly

$251 total

Feb 18 - Feb 19

Total with taxes and fees

9.2/10 Wonderful! (82 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	180 Cottages
Lowest Price	$161
Highest Price	$559
Popular accommodation	Streamside Cottage Half Mile to Town of Woodstock, Experience Peace in this Cozy country cottage nestled beneath the mountains, Dual-Dwelling Catskill Getaway Near Belleayre & Plattekill, Charming Cottage in Private Lake Community (Pet-Friendly!), Country Cottage with beautiful views and easy access to Catskills activities., Junebug Cottage: peace, love and privacy a short walk to Woodstock village green, Little red house just outside of Woodstock, Charming Artist's Retreat, Private Home ~ All Yours ~ In town ~ fenced in yard ~ Pets welcome!