Book Holiday Homes in Windham

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Featured Holiday Homes in Windham

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

Athens
Located in Coxsackie, this vacation home is on the waterfront, a 1-minute drive from Sleepy Hollow Lake and 6 minutes from Hudson River Islands State Park.
Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing
Quaint Cottage with Peloton Bike & Sauna near Skiing

Quaint Cottage with Peloton Bike & Sauna near Skiing

Mount Tremper
With a stay at this vacation home in Mount Tremper, you'll be in the mountains, within a 10-minute drive of Catskill Mountains and Catskill State Park.
Quaint Cottage with Peloton Bike & Sauna near Skiing
Magical Home Located in Windham and Catskills

Magical Home Located in Windham and Catskills

2 out of 5
Windham
With a stay at this vacation home in Windham, you'll be within a 10-minute drive of Windham Mountain Resort and Catskill State Park.
Magical Home Located in Windham and Catskills
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The Tipsy Gypsy

The Tipsy Gypsy

Hunter
The price is AU$718 per night from 2 Mar to 3 Mar
AU$718
includes taxes & fees
2 Mar - 3 Mar
With a stay at this vacation home in Hunter, you'll be within a 5-minute drive of Hunter Mountain and Catskill State Park.
The Tipsy Gypsy
 Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Windham
The price is AU$239 per night from 12 Mar to 13 Mar
AU$239
includes taxes & fees
12 Mar - 13 Mar
With a stay at this vacation home, you'll be centrally located in Windham, within a 5-minute drive of Windham Mountain Resort and Catskill State Park.
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres,  Ski Lodge

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

Windham
With a stay at this vacation home in Windham, you'll be on a river, within a 10-minute drive of Windham Mountain Resort and Catskill State Park.
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
A world where time stands still, close to Belleayre Ski & Wedding venues.

A world where time stands still, close to Belleayre Ski & Wedding venues.

City Roxbury
The price is AU$835 per night from 2 Mar to 3 Mar
AU$835
includes taxes & fees
2 Mar - 3 Mar
Located in Denver, this vacation home is in the mountains, a 5-minute drive from East Branch Delaware River and 8 minutes from Pakatakan Farmers' Market.
A world where time stands still, close to Belleayre Ski & Wedding venues.
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!

SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!

Hunter
With a stay at this vacation home in Hunter, you'll be in the mountains, within a 5-minute drive of Hunter Mountain and Catskill State Park.
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
Cozy Country Farmhouse Along the Catskill Scenic Trail

Cozy Country Farmhouse Along the Catskill Scenic Trail

Hobart
The price is AU$504 per night from 6 Mar to 7 Mar
AU$504
includes taxes & fees
6 Mar - 7 Mar
When you stay at this vacation home in Hobart, you'll be in the mountains, within a 5-minute drive of Stamford Town Hall and Hobart Book Village.
Cozy Country Farmhouse Along the Catskill Scenic Trail
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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.

Windham Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Windham vacation homes are the perfect way for you to wing it.

Holiday houses in Windham let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Windham in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Windham adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Windham with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Windham vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Windham Holiday Homes essential information

Accommodation
635 Holiday Homes
Lowest Price
AU$239
Highest Price
AU$835
Popular accommodation
Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing, Quaint Cottage with Peloton Bike & Sauna near Skiing, Magical Home Located in Windham and Catskills, The Tipsy Gypsy, Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter, Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge, A world where time stands still, close to Belleayre Ski & Wedding venues. , SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!, Cozy Country Farmhouse Along the Catskill Scenic Trail

Top trending hotels in Windham

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296, Windham, NY
Fully refundableReserve now, pay when you stay
The price is AU$383 per night from 1 Mar to 2 Mar
AU$383
includes taxes & fees
1 Mar - 2 Mar
With a stay at Wylder Hotel Windham in Windham, you'll be within a 5-minute drive of Windham Mountain Resort and Catskill State Park.
Wylder Hotel Windham
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
The price is AU$270 per night from 6 Mar to 7 Mar
AU$270
includes taxes & fees
6 Mar - 7 Mar
When you stay at Hotel Vienna in Windham, you'll be next to a golf course, within a 5-minute drive of Windham Country Club and Windham Mountain Resort.
Hotel Vienna
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
The price is AU$338 per night from 2 Mar to 3 Mar
AU$338
includes taxes & fees
2 Mar - 3 Mar
With a stay at Eastwind Windham in Windham, you'll be within a 5-minute drive of Windham Mountain Resort and Catskill State Park.
Eastwind Windham
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Winwood Inn & Condominiums

Winwood Inn & Condominiums

3 out of 5
5220 NY-23, Windham, NY
The price is AU$287 per night from 2 Mar to 3 Mar
AU$287
includes taxes & fees
2 Mar - 3 Mar
With a stay at Winwood Inn & Condominiums in Windham, you'll be next to a golf course, within a 5-minute drive of Windham Mountain Resort and Catskill State ...
Winwood Inn & Condominiums
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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.

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^Subject to availability and chosen travel dates.