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Featured Cottages in Windham

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 barbecue grills and a garden.
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

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

Woodstock NY
Guests staying at this cottage have access to barbecue grills and a garden.
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Woodstock NY
$320 nightly
The price is $359 total per night
$359 total
Jun 5 - Jun 6
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

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

Catskill NY
$286 nightly
The price is $309 total per night
$309 total
May 26 - May 27
Total with taxes and fees
At this cottage, guests have access to laundry facilities, local meal delivery service, and a garden. Transportation is made easy with limo/town car service. Additional amenities include a living plant wall and barbecue grills.
Charming Artist's Retreat

Charming Artist's Retreat

Saugerties NY
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly

Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly

Woodstock NY
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, barbecue grills, and a garden.
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, a garden, and barbecue grills.
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

Woodstock NY
Guests of this cottage enjoy features like spa services, a terrace and laundry facilities. Additional amenities include barbecue grills and a garden.
Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

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

    Eastwind Windham

    Eastwind Windham

    5088 NY-23 Windham NY
    $249 nightly
    The price is $268 total per night from May 25 to May 26
    $268 total
    May 25 - May 26
    Total with taxes and fees
    9.2/10 Wonderful! (102 reviews)
    Wylder Hotel Windham

    Wylder Hotel Windham

    19 New York 296 Windham NY
    $306 nightly
    The price is $331 total per night from May 25 to May 26
    $331 total
    May 25 - May 26
    Total with taxes and fees
    8.8/10 Excellent! (98 reviews)
    Hotel Vienna

    Hotel Vienna

    107 State Route 296 Windham NY
    $175 nightly
    The price is $189 total per night from May 25 to May 26
    $189 total
    May 25 - May 26
    Total with taxes and fees
    9.4/10 Exceptional! (801 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
187 Cottages
Lowest Price
$189
Highest Price
$359
Popular accommodation
The Cabin at Chichester in the Catskills Mountains, Junebug Cottage: peace, love and privacy a short walk to Woodstock village green, Streamside Cottage Half Mile to Town of Woodstock, Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill, Charming Artist's Retreat, Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly, ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!, Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

More to Explore