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$722 per night from 26 Feb to 27 Feb
AU$722
includes taxes & fees
26 Feb - 27 Feb
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$241 per night from 10 Feb to 11 Feb
AU$241
includes taxes & fees
10 Feb - 11 Feb
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
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$509 per night from 9 Feb to 10 Feb
AU$509
includes taxes & fees
9 Feb - 10 Feb
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
Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

Fleischmanns
The price is AU$497 per night from 9 Feb to 10 Feb
AU$497
includes taxes & fees
9 Feb - 10 Feb
Located in Fleischmanns, this vacation home is within a 15-minute drive of Belleayre Mountain Ski Center and Catskill Mountains.
Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit
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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
628 Holiday Homes
Lowest Price
AU$241
Highest Price
AU$722
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, SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!, Cozy Country Farmhouse Along the Catskill Scenic Trail, Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

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
The price is AU$248 per night from 28 Jan to 29 Jan
AU$248
includes taxes & fees
28 Jan - 29 Jan
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$478 per night from 28 Jan to 29 Jan
AU$478
includes taxes & fees
28 Jan - 29 Jan
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$391 per night from 28 Jan to 29 Jan
AU$391
includes taxes & fees
28 Jan - 29 Jan
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$289 per night from 28 Jan to 29 Jan
AU$289
includes taxes & fees
28 Jan - 29 Jan
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.