Book Holiday Homes in Windham

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Windham

The Catskills Red Barn-near Belleayre

The Catskills Red Barn-near Belleayre

Highmount
Stay at this vacation home in Highmount. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Belleayre Mountain Ski Center and Pine Hill ...
Opens in a new windowThe Catskills Red Barn-near Belleayre
Catskill Nest, spacious 3-bedroom country chateau

Catskill Nest, spacious 3-bedroom country chateau

Catskill, NY
Stay at this vacation home in Catskill. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Greene County Council on the Arts and Thomas Cole ...
Opens in a new windowCatskill Nest, spacious 3-bedroom country chateau
7Bdr/5Bth, Amazing View, Lake/Swim. 1/2 ml Ski Hunter Resort, Hot Tub/Sauna.Golf

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

Lanesville, Hunter
The price is NZ$1,579 per night from 10 Nov to 11 Nov
NZ$1,579
10 Nov - 11 Nov
includes taxes & fees
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 ...
Opens in a new window7Bdr/5Bth, Amazing View, Lake/Swim. 1/2 ml Ski Hunter Resort, Hot Tub/Sauna.Golf
Save an average of 15% on thousands of hotels when you're signed in
Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook

Catskill
The price is NZ$598 per night from 12 Nov to 13 Nov
NZ$598
12 Nov - 13 Nov
includes taxes & fees
Stay at this vacation home in Catskill. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Angelo Canna Town Park and Catskill Golf Club ...
Opens in a new windowModern Luxurious Cabin, Catskills - The Tiny Nook
Charming Catskill getaway walking distance to Main St. Pet-friendly!

Charming Catskill getaway walking distance to Main St. Pet-friendly!

Catskill
Stay at this vacation home in Catskill. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Thomas Cole National Historic ...
Opens in a new windowCharming Catskill getaway walking distance to Main St. Pet-friendly!
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly

Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly

Woodstock
Stay at this vacation home in Woodstock. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Colony and Woodstock Public Library are located ...
Opens in a new windowIconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
Magical Home Located in Windham and Catskills

Magical Home Located in Windham and Catskills

2 out of 5
Windham
Stay at this vacation home in Windham. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Windham Mountain Resort and Ashland Park are located ...
Opens in a new windowMagical Home Located in Windham and Catskills
Tranquil 2-bedroom house with AC in Cornwallville nestled on 23 acres

Tranquil 2-bedroom house with AC in Cornwallville nestled on 23 acres

2 out of 5
Cornwallville
Stay at this vacation home in Cornwallville. Enjoy in-room fireplaces and air conditioning. Popular attractions Durham Center Museum and Irish Cultural Center ...
Opens in a new windowTranquil 2-bedroom house with AC in Cornwallville nestled on 23 acres
Waterfront Luxe: Chef’s Kitchen, Pong & Air Hockey, Near Hudson, Ski Hunter Mntn

Waterfront Luxe: Chef’s Kitchen, Pong & Air Hockey, Near Hudson, Ski Hunter Mntn

Athens
Book a stay at this family-friendly vacation home in Coxsackie. Enjoy free WiFi, 4 outdoor pickleball courts, and a garden. Popular attractions Sleepy Hollow ...
Opens in a new windowWaterfront Luxe: Chef’s Kitchen, Pong & Air Hockey, Near Hudson, Ski Hunter Mntn
Don't see what you're looking for?
See all available properties in Windham
View all properties
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
733 Holiday Homes
Lowest Price
NZ$320
Highest Price
NZ$1,579
Popular accommodation
The Catskills Red Barn-near Belleayre, Catskill Nest, spacious 3-bedroom country chateau, 7Bdr/5Bth, Amazing View, Lake/Swim. 1/2 ml Ski Hunter Resort, Hot Tub/Sauna.Golf, Modern Luxurious Cabin, Catskills - The Tiny Nook, Charming Catskill getaway walking distance to Main St. Pet-friendly!, Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly, Magical Home Located in Windham and Catskills, Tranquil 2-bedroom house with AC in Cornwallville nestled on 23 acres, Waterfront Luxe: Chef’s Kitchen, Pong & Air Hockey, Near Hudson, Ski Hunter Mntn

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. ...
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 NZ$376 per night from 16 Nov to 17 Nov
NZ$376
16 Nov - 17 Nov
includes taxes & fees
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 ...
Opens in a new windowWylder Hotel Windham
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
The price is NZ$413 per night from 26 Nov to 27 Nov
NZ$413
26 Nov - 27 Nov
includes taxes & fees
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Windham Mountain Resort and Windham Country Club ...
Opens in a new windowEastwind Windham
Save an average of 15% on thousands of hotels when you're signed in
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3 out of 5
5220 NY-23, Windham, NY
Fully refundableReserve now, pay when you stay
The price is NZ$320 per night from 6 Nov to 7 Nov
NZ$320
6 Nov - 7 Nov
includes taxes & fees
Stay at this 3-star ski hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country ...
Opens in a new windowWinwood Condominiums by Windham Mountain Club
Don't see what you're looking for?
See all available properties in Windham
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.