Book Holiday Homes in Windham

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Featured Holiday Homes in Windham

HOT TUB w/ POOL,  STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

Woodstock
A stay at this vacation home places you in the heart of Woodstock, steps from Catskill State Park and a 4-minute drive from Woodstock Music Shop.
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN
 Beautiful new house 3/4  mile from Hunter Mountain

Beautiful new house 3/4 mile from Hunter Mountain

hunter
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.
Beautiful new house 3/4 mile from Hunter Mountain
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$769 per night from 8 Apr to 9 Apr
AU$769
includes taxes & fees
8 Apr - 9 Apr
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.
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Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

Fleischmanns
Located in Fleischmanns, this vacation home is in the mountains, a 4-minute drive from East Branch Delaware River and 6 minutes from Pakatakan Farmers' ...
Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville
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.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

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 Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
A'Neils Windham Ski Lodge & Family Retreat

A'Neils Windham Ski Lodge & Family Retreat

Windham
With a stay at this vacation home in Windham, you'll be on a lake, within a 10-minute drive of Windham Mountain Resort and Catskill State Park.
A'Neils Windham Ski Lodge & Family Retreat
7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

Lanesville, Hunter
The price is AU$1,172 per night from 7 Apr to 8 Apr
AU$1,172
includes taxes & fees
7 Apr - 8 Apr
With a stay at this vacation home, you'll be centrally located in Hunter, within a 5-minute drive of Hunter Mountain and Catskill State Park.
7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim
Catskills Cozy Cottage with Peloton & Sauna near Hunter  and Belleayre Mountain

Catskills Cozy Cottage with Peloton & Sauna near Hunter and Belleayre Mountain

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.
Catskills Cozy Cottage with Peloton & Sauna near Hunter and Belleayre Mountain
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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
821 Holiday Homes
Lowest Price
AU$240
Highest Price
AU$1,172
Popular accommodation
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN, Beautiful new house 3/4 mile from Hunter Mountain , A world where time stands still, close to Belleayre Ski & Wedding venues. , Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub, Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat, SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!, A'Neils Windham Ski Lodge & Family Retreat, 7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim, Catskills Cozy Cottage with Peloton & Sauna near Hunter and Belleayre Mountain

Top trending hotels in Windham

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
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
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$482 per night from 9 Apr to 10 Apr
AU$482
includes taxes & fees
9 Apr - 10 Apr
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
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
The price is AU$343 per night from 6 Apr to 7 Apr
AU$343
includes taxes & fees
6 Apr - 7 Apr
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$240 per night from 6 Apr to 7 Apr
AU$240
includes taxes & fees
6 Apr - 7 Apr
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.