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
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.
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.

Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.

Prattsville
Located in Prattsville, this vacation home is on the waterfront, a 1-minute drive from Catskill State Park and 9 minutes from Prattsville Town Hall.
Opens in a new windowPrivate Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.
 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.
Opens in a new window Beautiful new house 3/4 mile from Hunter Mountain
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Catskills Getaway Home W/ Hot tub, Game room, fire pit and basketball court

Catskills Getaway Home W/ Hot tub, Game room, fire pit and basketball court

Margaretville
The price is AU$1,027 per night from 21 Sept to 22 Sept
AU$1,027
21 Sept - 22 Sept
includes taxes & fees
Located in Margaretville, this vacation home is on a lake, within a 10-minute drive of Pakatakan Farmers' Market and East Branch Delaware River.
Opens in a new windowCatskills Getaway Home W/ Hot tub, Game room, fire pit and basketball court
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$511 per night from 19 Oct to 20 Oct
AU$511
19 Oct - 20 Oct
includes taxes & fees
With a stay at this vacation home in Fleischmanns, you'll be within a 15-minute drive of Catskill Mountains and Catskill State Park.
Opens in a new windowFree 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit
Peaceful River Retreat with Fireplace & Panoramic Views

Peaceful River Retreat with Fireplace & Panoramic Views

Cementon
Located in Catskill, this vacation home is on the waterfront, within a 10-minute drive of Bristol Beach State Park and George J. Terpening Sr. Memorial ...
Opens in a new windowPeaceful River Retreat with Fireplace & Panoramic Views
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

Chichester
With a stay at this vacation home in Chichester, you'll be on the waterfront, within a 10-minute drive of Catskill Mountains and Catskill State Park.
Opens in a new windowCREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

2 out of 5
Phoenicia
The price is AU$522 per night from 28 Sept to 29 Sept
AU$522
28 Sept - 29 Sept
includes taxes & fees
When you stay at this vacation home in Phoenicia, you'll be in the mountains, within a 15-minute walk of Catskill Mountains and Catskill State Park.
Opens in a new window1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
9BR/5BR/Hottub/2 Saunas 6 min to Hunter on 30 private acres

9BR/5BR/Hottub/2 Saunas 6 min to Hunter on 30 private acres

Hunter
With a stay at this vacation home in Hunter, you'll be within a 10-minute drive of Hunter Mountain and Catskill State Park.
Opens in a new window9BR/5BR/Hottub/2 Saunas 6 min to Hunter on 30 private acres
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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
823 Holiday Homes
Lowest Price
AU$305
Highest Price
AU$1,027
Popular accommodation
A world where time stands still, close to Belleayre Ski & Wedding venues. , Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking., Beautiful new house 3/4 mile from Hunter Mountain , Catskills Getaway Home W/ Hot tub, Game room, fire pit and basketball court, Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit, Peaceful River Retreat with Fireplace & Panoramic Views, CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts., 1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard, 9BR/5BR/Hottub/2 Saunas 6 min to Hunter on 30 private acres

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$420 per night from 21 Sept to 22 Sept
AU$420
21 Sept - 22 Sept
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$356 per night from 13 Oct to 14 Oct
AU$356
13 Oct - 14 Oct
includes taxes & fees
With a stay at Eastwind Windham in Windham, you'll be within a 5-minute drive of Windham Mountain Resort and Catskill State Park.
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$305 per night from 24 Sept to 25 Sept
AU$305
24 Sept - 25 Sept
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.