Book Holiday Homes in Windham

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Featured Holiday Homes in Windham

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 NY
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.
Opens in a new windowA world where time stands still, close to Belleayre Ski & Wedding venues.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville NY
With a stay at this vacation home in Bearsville, you'll be in the mountains, within a 15-minute drive of Catskill Mountains and Catskill State Park.
Opens in a new windowLuxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Maplewood Manor, 8BR w/ Hot Tub, Gym, Fire Pit, Near Hunter/Windham Skiing

Maplewood Manor, 8BR w/ Hot Tub, Gym, Fire Pit, Near Hunter/Windham Skiing

Jewett NY
With a stay at this vacation home in Hunter, you'll be within a 15-minute drive of Hunter Mountain and Windham Mountain Resort.
Opens in a new windowMaplewood Manor, 8BR w/ Hot Tub, Gym, Fire Pit, Near Hunter/Windham Skiing
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Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths Sauna great location

Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths Sauna great location

Lanesville NY
With a stay at this vacation home in Hunter, you'll be on the waterfront, within a 5-minute drive of Hunter Mountain and Catskill State Park.
Opens in a new windowBest rated cabin in Hunter cozy 4 Bedrooms 3 full baths Sauna great location
Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!

Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!

Windham NY
With a stay at this vacation home in Windham, you'll be in the mountains, within a 10-minute drive of Windham Mountain Resort and Windham Country Club.
Opens in a new windowTimber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
Your peaceful, private retreat, escape with friends & family! Incredible views!

Your peaceful, private retreat, escape with friends & family! Incredible views!

Oak Hill NY
With a stay at this vacation home in Medusa, you'll be in the mountains, and 25.6 mi (41.2 km) from Hunter Mountain and 16.3 mi (26.3 km) from Windham Mountain ...
Opens in a new windowYour peaceful, private retreat, escape with friends & family! Incredible views!
Birch Creek Mountain House- 3 minutes to Belleayre Mtn

Birch Creek Mountain House- 3 minutes to Belleayre Mtn

Big Indian NY
When you stay at this vacation home in Pine Hill, you'll be on the waterfront, within a 5-minute drive of Catskill Mountains and Belleayre Mountain Ski ...
Opens in a new windowBirch Creek Mountain House- 3 minutes to Belleayre Mtn
StarryPinesCottage w Salt Hot Tub & Cedar Sauna Mins to Slopes

StarryPinesCottage w Salt Hot Tub & Cedar Sauna Mins to Slopes

Catskill NY
Located in Palenville, this vacation home is a 1-minute drive from Catskill State Park and 5 minutes from Vinnie's Farm Market.
Opens in a new windowStarryPinesCottage w Salt Hot Tub & Cedar Sauna Mins to Slopes
7-bedroom Mountain Mansion of Belleayre! + POOL, SAUNA, GAME ROOM, AC and MORE

7-bedroom Mountain Mansion of Belleayre! + POOL, SAUNA, GAME ROOM, AC and MORE

Fleischmanns NY
The price is AU$2,974 per night from 4 Feb to 5 Feb
AU$2,974
4 Feb - 5 Feb
includes taxes & fees
With a stay at this vacation home in Fleischmanns, you'll be a 4-minute drive from Belleayre Mountain Ski Center and 9 minutes from Catskill Mountains.
Opens in a new window7-bedroom Mountain Mansion of Belleayre! + POOL, SAUNA, GAME ROOM, AC and MORE
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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
711 Holiday Homes
Lowest Price
AU$309
Highest Price
AU$2,974
Popular accommodation
A world where time stands still, close to Belleayre Ski & Wedding venues. , Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat, Maplewood Manor, 8BR w/ Hot Tub, Gym, Fire Pit, Near Hunter/Windham Skiing, Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths Sauna great location, Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!, Your peaceful, private retreat, escape with friends & family! Incredible views!, Birch Creek Mountain House- 3 minutes to Belleayre Mtn, StarryPinesCottage w Salt Hot Tub & Cedar Sauna Mins to Slopes, 7-bedroom Mountain Mansion of Belleayre! + POOL, SAUNA, GAME ROOM, AC and MORE

Top trending hotels in Windham

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296 Windham NY
Fully refundableReserve now, pay when you stay
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.
Opens in a new windowHotel Vienna
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
The price is AU$363 per night from 4 Feb to 5 Feb
AU$363
4 Feb - 5 Feb
includes taxes & fees
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.
Opens in a new windowWylder Hotel Windham
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23 Windham NY
The price is AU$386 per night from 6 Feb to 7 Feb
AU$386
6 Feb - 7 Feb
includes taxes & fees
When you stay at Eastwind Windham in Windham, you'll be next to a golf course, just steps from Catskill State Park and 10 minutes by foot from Windham Country ...
Opens in a new windowEastwind Windham
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Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3 out of 5
5220 NY-23 Windham NY
The price is AU$309 per night from 4 Feb to 5 Feb
AU$309
4 Feb - 5 Feb
includes taxes & fees
With a stay at Winwood Condominiums by Windham Mountain Club in Windham, you'll be in the business district, within a 5-minute drive of Windham Mountain Resort ...
Opens in a new windowWinwood Condominiums by Windham Mountain Club
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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.