Compare Windham Cottage Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Cottages in Windham

Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Woodstock NY
$301 nightly
The price is $337 total per night
$337 total
Nov 4 - Nov 5
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Free WiFi
Country Cottage with beautiful views and easy access to Catskills activities.

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

Saugerties NY
Guests staying at this cottage have access to barbecue grills and a garden.
Pet friendly
Free WiFi
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Catskill NY
$295 nightly
The price is $318 total per night
$318 total
Oct 13 - Oct 14
Total with taxes and fees
At this cottage, guests have access to laundry facilities, local meal delivery service, and a living plant wall. Transportation is made easy with limo/town car service. Additional amenities include barbecue grills and a garden.
Kitchen
Washer
Charming Artist's Retreat

Charming Artist's Retreat

Saugerties NY
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
The Cabin at Chichester in the Catskills Mountains

The Cabin at Chichester in the Catskills Mountains

Chichester NY
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Pet friendly
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

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

Phoenicia NY
This cottage features a hot tub and a garden. This smoke-free cottage also has barbecue grills.
Hot Tub
Kitchen
Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly

Catskill NY
$316 nightly
The price is $354 total per night
$354 total
Oct 12 - Oct 13
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

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

Woodstock NY
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Private Woodstock Retreat • Walk to Town • Hot Tub

Private Woodstock Retreat • Walk to Town • Hot Tub

Woodstock NY
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. This cottage also has a garden.
Hot Tub
Kitchen
Don't see what you're looking for?
See all available properties in Windham
View all properties
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
    $145 nightly
    The price is $157 total per night from Oct 29 to Oct 30
    $157 total
    Oct 29 - Oct 30
    Total with taxes and fees
    9.4/10 Exceptional! (881 reviews)
    Wylder Hotel Windham

    Wylder Hotel Windham

    19 New York 296 Windham NY
    $342 nightly
    The price is $370 total per night from Oct 11 to Oct 12
    $370 total
    Oct 11 - Oct 12
    Total with taxes and fees
    Eastwind Windham

    Eastwind Windham

    5088 NY-23 Windham NY
    $319 nightly
    The price is $344 total per night from Oct 7 to Oct 8
    $344 total
    Oct 7 - Oct 8
    Total with taxes and fees
    9.2/10 Wonderful! (121 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
$370
Popular accommodation
Streamside Cottage Half Mile to Town of Woodstock, Country Cottage with beautiful views and easy access to Catskills activities., Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill, Charming Artist's Retreat, The Cabin at Chichester in the Catskills Mountains, Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!, Charming Cottage in the Heart of Catskill & Pet Friendly, ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, Private Woodstock Retreat • Walk to Town • Hot Tub

More to Explore