Holiday rentals near Windham Country Club
We found 1,444 holiday rentals — enter your dates for availability
Find the perfect private holiday rental within easy reach of Windham Country Club. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as Wi-Fi and cable TV. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Windham Country Club
Showing deals for:26 Sept - 3 Oct
Image gallery for Minutes to Skiing, Hot Tub, Fire Pit, 10 Acres, Mtn Views, Private Pond
1010 out of 10 rating
Exceptional
(5 reviews)
Minutes to Skiing, Hot Tub, Fire Pit, 10 Acres, Mtn Views, Private Pond
Medusa, NY
18% off
Price is AU$7,420
AU$7,420
AU$1,060 per night
includes taxes & fees
Image gallery for Magical Home Located in Windham and Catskills
1010 out of 10 rating
Exceptional
(9 reviews)
Magical Home Located in Windham and Catskills
Windham, NY
12% off
Price is AU$3,985
AU$3,985
AU$569 per night
includes taxes & fees
Image gallery for Private Getaway 10 Mins From Hunter & Windham Mountain
9.89.8 out of 10 rating
Exceptional
(87 reviews)
Private Getaway 10 Mins From Hunter & Windham Mountain
Hunter, NY
12% off
Price is AU$4,453
AU$4,453
AU$636 per night
includes taxes & fees
Image gallery for Sunset Mountain Retreat - mins from Woodstock
1010 out of 10 rating
Exceptional
(20 reviews)
Sunset Mountain Retreat - mins from Woodstock
Mount Tremper, NY
11% off
Price is AU$6,335
AU$6,335
AU$905 per night
includes taxes & fees
Image gallery for Don’t miss Cooperstown baseball hall of fame weekend! LOG CABIN still available!
1010 out of 10 rating
Exceptional
(12 reviews)
Don’t miss Cooperstown baseball hall of fame weekend! LOG CABIN still available!
North Blenheim, NY
14% off
Price is AU$4,389
AU$4,389
AU$627 per night
includes taxes & fees
Image gallery for Quiet Mountain View Art House - Up on a hill - Round Top!
1010 out of 10 rating
Exceptional
(5 reviews)
Quiet Mountain View Art House - Up on a hill - Round Top!
Round Top, NY
8% off
Price is AU$7,255
AU$7,255
AU$1,036 per night
includes taxes & fees
Image gallery for Cheerful 3-bedroom cabin with mountain view
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Cheerful 3-bedroom cabin with mountain view
East Jewett, NY
15% off
Price is AU$3,167
AU$3,167
AU$452 per night
includes taxes & fees
Image gallery for 'Sundance Vistas - Log Home ' - 2 Miles From Windham Ski Mountain
1010 out of 10 rating
Exceptional
(10 reviews)
'Sundance Vistas - Log Home ' - 2 Miles From Windham Ski Mountain
Windham, NY
11% off
Price is AU$14,859
AU$14,859
AU$2,123 per night
includes taxes & fees
Image gallery for Chalet w/HOT TUB & OUTDOOR TV, Fire Pit, Pool Nearby, Prvt. trail & playground!
1010 out of 10 rating
Exceptional
(21 reviews)
Chalet w/HOT TUB & OUTDOOR TV, Fire Pit, Pool Nearby, Prvt. trail & playground!
Gilboa, NY
8% off
Price is AU$3,863
AU$3,863
AU$552 per night
includes taxes & fees
Image gallery for Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.
1010 out of 10 rating
Exceptional
(68 reviews)
Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.
Bearsville, NY
8% off
Price is AU$8,536
AU$8,536
AU$1,219 per night
includes taxes & fees
Image gallery for Belleayre View: Paramount Views, Hot Tub + Firepit
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Belleayre View: Paramount Views, Hot Tub + Firepit
Fleischmanns, New York
12% off
Price is AU$5,021
AU$5,021
AU$717 per night
includes taxes & fees
Image gallery for Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
1010 out of 10 rating
Exceptional
(5 reviews)
Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
West Kill, NY
31% off
Price is AU$3,340
AU$3,340
AU$477 per night
includes taxes & fees
Image gallery for July 4th now available. Inquire about discount. Pool, gourmet kitchen, views!
1010 out of 10 rating
Exceptional
(85 reviews)
July 4th now available. Inquire about discount. Pool, gourmet kitchen, views!
Tannersville, NY
7% off
Price is AU$15,434
AU$15,434
AU$2,205 per night
includes taxes & fees
Image gallery for PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
9.89.8 out of 10 rating
Exceptional
(6 reviews)
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Mount Tremper, NY
6% off
Price is AU$3,600
AU$3,600
AU$514 per night
includes taxes & fees
Image gallery for BREATHTAKING VIEWS, Contemporary, located 2,500' off road, 25 acre estate!
1010 out of 10 rating
Exceptional
(5 reviews)
BREATHTAKING VIEWS, Contemporary, located 2,500' off road, 25 acre estate!
Windham, NY
8% off
Price is AU$6,159
AU$6,159
AU$880 per night
includes taxes & fees
Image gallery for Modern Cottage 1 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Modern Cottage 1 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Shandaken, NY
8% off
Price is AU$2,346
AU$2,346
AU$335 per night
includes taxes & fees
Image gallery for Golf, Ski, Hike great for wedding guests
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Golf, Ski, Hike great for wedding guests
Roxbury, NY
19% off
Price is AU$2,867
AU$2,867
AU$410 per night
includes taxes & fees
Image gallery for Catskill Mountain Hideaway with Amazing Hunter Mountain Views
1010 out of 10 rating
Exceptional
(12 reviews)
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Hunter, NY
17% off
Price is AU$6,709
AU$6,709
AU$958 per night
includes taxes & fees
Image gallery for Newly Built 1200sq ft Guest House 4min to Ski & Hiking
1010 out of 10 rating
Exceptional
(9 reviews)
Newly Built 1200sq ft Guest House 4min to Ski & Hiking
Windham, NY
8% off
Price is AU$3,314
AU$3,314
AU$473 per night
includes taxes & fees
Image gallery for THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need
9.89.8 out of 10 rating
Exceptional
(7 reviews)
THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need
Saugerties, NY
9% off
Price is AU$4,054
AU$4,054
AU$579 per night
includes taxes & fees
Image gallery for Rustic Quarry Luxury with Private Lake
1010 out of 10 rating
Exceptional
(6 reviews)
Rustic Quarry Luxury with Private Lake
Saugerties, NY
17% off
Price is AU$13,713
AU$13,713
AU$1,959 per night
includes taxes & fees
Image gallery for Blissful getaway with epic views
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Blissful getaway with epic views
Denver, NY
5% off
Price is AU$3,794
AU$3,794
AU$542 per night
includes taxes & fees
Image gallery for Windham getaway!
1010 out of 10 rating
Exceptional
(7 reviews)
Windham getaway!
Windham, NY
8% off
Price is AU$2,177
AU$2,177
AU$311 per night
includes taxes & fees
Image gallery for Modern Rustic Log Chalet w/ mtn views, pool & bonus loft on 17 secluded acres
1010 out of 10 rating
Exceptional
(23 reviews)
Modern Rustic Log Chalet w/ mtn views, pool & bonus loft on 17 secluded acres
Grand Gorge, NY
8% off
Price is AU$4,725
AU$4,725
AU$675 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
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Chalet
Find the best place to stay - Windham Country Club
Showing deals for: 23 Sept - 26 Sept
2025 Log Home- Ski Chalet w/ Luxury Amenities. direct Views of Hunter Slopes
Sleeps 16 · 6 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
The current price is AU$9,443
AU$9,443
for 3 nights, 1 home
AU$3,148 per night
includes taxes & fees
Charming 5-bedroom Lake Log cabin in marvelous Lanesville
Sleeps 16 · 5 bedrooms · 4+ bathrooms
The current price is AU$4,414
AU$4,414
for 3 nights, 1 cabin
AU$1,471 per night
includes taxes & fees
6BR/7bath Luxury home Hot Tub in Hunter Catskills
Sleeps 24 · 6 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is AU$3,296
AU$3,296
for 3 nights, 1 home
AU$1,099 per night
includes taxes & fees
The Hunter Chalet
Sleeps 26 · 9 bedrooms · 7 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
The current price is AU$8,114
AU$8,114
for 3 nights, 1 chalet
AU$2,705 per night
includes taxes & fees
*The View* ski in/out modern luxury at Windham Mountain Resort
Sleeps 14 · 5 bedrooms · 5+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
The current price is AU$11,044
AU$11,044
for 3 nights, 1 home
AU$3,681 per night
includes taxes & fees
Spacious 6BR Catskills Mountain Getaway with Hot Tub & Stunning Views
Sleeps 14 · 6 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
127 reviews(127 reviews)
The current price is AU$5,072
AU$5,072
for 3 nights, 1 home
AU$1,691 per night
includes taxes & fees
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value