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
Book a stay at this family-friendly vacation home in Woodstock. Enjoy free WiFi, private pools, and a water park. Popular attractions Woodstock Public Library ...
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
Book a stay at this family-friendly vacation home in Hunter. Enjoy a garden, a pool table, and patios. Popular attractions Hunter Mountain and Windham Mountain ...
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
Stay at this vacation home in Denver. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Pakatakan Farmers' Market and Plattekill State Forest ...
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
Stay at this vacation home in Fleischmanns. Enjoy free WiFi, a garden, and patios. Popular attractions Belleayre Mountain Ski Center and Pakatakan Farmers' Market ...
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
Stay at this vacation home in Bearsville. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Mount Tremper Arts and Emerson Place Kaleidoscope ...
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
Stay at this vacation home in Hunter. Enjoy free WiFi, a garden, and patios. Popular attractions Hunter Mountain and H Ski Lift are located nearby.
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
Book a stay at this ski vacation home in Windham. Enjoy free WiFi, a water park, and a garden. Popular attractions Windham Mountain Resort and Ashland Park are ...
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 NZ$1,266 per night from 2 Apr to 3 Apr
NZ$1,266
includes taxes & fees
2 Apr - 3 Apr
Book a stay at this beach vacation home in Hunter. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Hunter Mountain and Windham Mountain ...
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
Stay at this vacation home in Mount Tremper. Enjoy a fitness center, a garden, and an in-room coffeemaker. Popular attractions Mount Tremper Arts and Emerson ...
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
820 Holiday Homes
Lowest Price
NZ$378
Highest Price
NZ$1,266
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
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
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 NZ$534 per night from 2 Apr to 3 Apr
NZ$534
includes taxes & fees
2 Apr - 3 Apr
Stay at this 3.5-star hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club ...
Wylder Hotel Windham
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
The price is NZ$378 per night from 2 Apr to 3 Apr
NZ$378
includes taxes & fees
2 Apr - 3 Apr
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Windham Mountain Resort and Windham Country Club ...
Eastwind Windham
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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
Book a stay at this family-friendly vacation home in Windham. Enjoy free WiFi, a water park, and a fitness center. Our guests praise the helpful staff in our ...
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
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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.