Elm Ridge Wild Forest Rentals
From $264 per night (USD)VRBO
Windham Mtn! 2BR/2B, Sleeps 6-8. Wi-Fi. Ski, Fine Dining, Hike, Antiquing, More!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Private WiFi for Internet & cell calling. ========================================= QUADS CONDOMINIUM: 2 bedroom, 2 ba ...
From $264 per night (USD)VRBO
From $1053 per night (USD)Expedia
Stanley's Mountain Getaway · 5 Min to Skiing | Hot Tub | Fire Pit | Games | Bar
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Make lasting memories in this 5 BR, 3.5 BA, 5,600 ft² cabin in scenic Windham, NY located just 5 min away from Windham M ...
From $1053 per night (USD)Expedia
From $521 per night (USD)VRBO
Luxury Windham Mtn Slope Side 3 BDRM Condo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
All three bedrooms have on-suite bathrooms. (1King, 1 Queen, Bunkbeds (sleeps 4) The property features a heated pool a ...
From $521 per night (USD)VRBO
From $157 per night (USD)Expedia
Catskills Home, 5 Mins to Windham Mtn Resort!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Make your next trip to the Catskills one to remember when you stay at this 2-bedroom, 2-bath vacation rental! Located on ...
From $157 per night (USD)Expedia
From $265 per night (USD)VRBO
Relaxing Catskills Apt < 3 Mi to Windham Mountain!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Experience year-round adventures at this family-friendly home in the heart of Upstate New York! Boasting 2 bedrooms, 2 b ...
From $265 per night (USD)VRBO
From $256 per night (USD)Expedia
Spacious Apt w/ Yard: 3 Mi to Windham Mountain
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the heart of Upstate New York, this 2-bedroom, 2-bath apartment offers easy access to Windham’s best summer a ...
From $256 per night (USD)Expedia
From $470 per night (USD)VRBO
Located within 10 minutes from both Windham Mountain and Hunter Mountain!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Thank you for your interest in our home! After using this privately for the last few years… kids sports are getting in t ...
From $470 per night (USD)VRBO
From $607 per night (USD)Expedia
Luxury Home w/ Deck: Explore the Catskill Mtns!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to the Catskills with this Windham vacation rental! Boasting an open living space, stone fireplace, and fully equ ...
From $607 per night (USD)Expedia
From $1011 per night (USD)VRBO
Ski Mountain Chalet w/ Hot tub, Fireplace, Game Room -Windham Mountain
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
Completely renovated luxury ski mountain home in Hensonville, town of Windham. 1.2 acres , set back on a hill for privac ...
From $1011 per night (USD)VRBO
From $513 per night (USD)Expedia
Luxurious Mountain Retreat: Sauna, Hot Tub, Fire Pit & Park
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience an Inviting Mountain Retreat Escape to our 4BR, 2BA log home situated on a park-like property near Windham an ...
From $513 per night (USD)Expedia
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Stylish Mountain Escape w/ Hot Tub, 3 Miles to Ski
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape the noise of the city and experience pure Catskill bliss at this deluxe 3-bedroom, 2-bathroom home! Ideally situa ...
Click For PricingVRBO
From $201 per night (USD)Expedia
Cozy Catskills Getaway w/ Yard & Mtn Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Surrounded by stellar mountain views and endless all-season adventure, this vacation rental is an ideal spot to jumpstar ...
From $201 per night (USD)Expedia
From $241 per night (USD)VRBO
Cozy Gateway Gem for 2 at Widham
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A beautifully renovated condo at the Quads. Almost 600 sq of living space to your disposal with a separate bedroom and ...
From $241 per night (USD)VRBO
From $298 per night (USD)Expedia
Windham Chalet+Gorgeous View
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
We refer to the property and the "Winter Palace" due to its homeliness and European chalet charm. If you have visited th ...
From $298 per night (USD)Expedia
From $211 per night (USD)VRBO
Redwood Retreat in Windham - Pool! Tennis!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
True mountain getaway, just 2.5 hours from NYC!! Modern and clean 2 bedroom 2 bathroom townhouse minutes to Windham Mou ...
From $211 per night (USD)VRBO
From $281 per night (USD)Expedia
4 Mi to Windham Mtn: Immaculate Summer Getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ample Outdoor Space | 4 Miles to Windham Mountain Resort | Near Colgate Lake Just minutes from Windham, NY, this pristi ...
From $281 per night (USD)Expedia
From $181 per night (USD)VRBO
High Peak Heaven: Cozy Log Cabin on 1 Acre!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Nestled in the Catskill Mountains, this Windham 2-bedroom, 1.5-bath vacation rental cabin makes for the perfect retreat ...
From $181 per night (USD)VRBO
From $180 per night (USD)VRBO
3-Bedroom Family Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Comfortable, two-story, 7-room family home on an acre of land. Recently redecorated. Master bedroom has king-size bed, ...
From $180 per night (USD)VRBO
From $420 per night (USD)VRBO
Windham Mountain Chalet with Treehouse sleeps 15, Game Room & fireplace
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Large Four season country vacation house in the heart of the Windham wirh a beautiful trehouse. Close enough to all the ...
From $420 per night (USD)VRBO
From $806 per night (USD)Expedia
Catskills Windham Hunter Mountain Cabin Getaway
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Here is your ski weekend! This is Your cozy cabin getaway near Windham and Hunter! You can rejuvenate your senses surrou ...
From $806 per night (USD)Expedia
From $542 per night (USD)VRBO
BREATHTAKING VIEWS, Contemporary, located 2,500' off road, 25 acre estate!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Perfect mountain getaway for all seasons! Skiing, hiking, biking, golfing, fishing or just relaxing! Enjoy the best of ...
From $542 per night (USD)VRBO
From $775 per night (USD)Expedia
Windham Moutain Ski House: Walk on & off Slopes - Families Only!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
FAMILIES ONLY, PLEASE. NO PARTIES! Family weekend home that we rent when we go skiing out West. Walk down steps behind ...
From $775 per night (USD)Expedia
From $328 per night (USD)VRBO
4 bedroom house 10 minutes to Windham Mountain
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Quiet 4 bedroom house with a nice sized living room with an indoor fireplace, a sunroom with beautiful views, a dining r ...
From $328 per night (USD)VRBO
From $1053 per night (USD)Expedia
Windham Farmhouse Escape w/hot tub
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Set on 8+ acres, this former dairy farm is a breath of fresh air. The farmhouse, built in 1838, maintains its original c ...
From $1053 per night (USD)Expedia
From $273 per night (USD)VRBO
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Make this spacious, newly built townhouse yours during a relaxing getaway in the Catskill Mountains! Located just minute ...
From $273 per night (USD)VRBO
From $607 per night (USD)VRBO
Country Escape Overlooking Hunter & Windham Mts
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Summary: Situated on 5 secluded acres between Windham & Hunter Mt, this 5-bdrm, 5-bath chalet can handle a large family, ...
From $607 per night (USD)VRBO
From $1431 per night (USD)VRBO
Serendipity Lake House on Lake Heloise. Beautiful private 4000 sq ft lodge
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 15
Enjoy a relaxing stay at this gorgeous rustic lodge on 10 acres abutting a 28 acre lake surrounded bybover 300 avrea of ...
From $1431 per night (USD)VRBO
From $246 per night (USD)Expedia
LUXURY SUITE WITH 2 FULL BEDS
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
➤ Escape to a Nature Immersive Retreat in the Catskills, with Haus Windham Vacation Rentals! • Perfect for any Guest see ...
From $246 per night (USD)Expedia
From $264 per night (USD)VRBO
Newly Renovated Ski House in Windham
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our charming and cozy retreat in the heart of Windham, where modern comfort meets historic charm. With its pr ...
From $264 per night (USD)VRBO
From $980 per night (USD)VRBO
BRAND NEW completely renovated house in Windham, 5 bed/ 3 bath
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to our beautiful, cozy mountain retreat! Our beautiful and spacious home is brand new and completely renovated. ...
From $980 per night (USD)VRBO
From $755 per night (USD)VRBO
Après Chalet|Ski|Luxury|Sauna|HotTub|Firepit|Disco
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
About this space Nestled in the heart of the Catskills, this Windham retreat offers both adventure and serenity, just 5 ...
From $755 per night (USD)VRBO
From $364 per night (USD)Expedia
Cozy Mtn-View Chalet < 2 Mi to Windham Slopes
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Private Hot Tub | Scenic Fireside Setting | Easy Access to Windham & Hunter Mountain Skiing There's no shortage of scen ...
From $364 per night (USD)Expedia
From $1377 per night (USD)VRBO
Reduced May Rates - Plus Special Culinary Promotion! Details Below!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Reduced May Rates - Plus Special Culinary Promotion! Details Below! Breathtaking Design, Newly Constructed Farmhouse wit ...
From $1377 per night (USD)VRBO
From $308 per night (USD)Expedia
All-Season Condo - Ski Windham l Hunter l Pool l Hike l Fish
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in this serene, inviting condo, a haven for year-round relaxation. Experience the natural splendor of the Catskil ...
From $308 per night (USD)Expedia
From $800 per night (USD)VRBO
Drift Haus|4.5BR+ Mountain Lodge
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Escape the ordinary at this spacious alpine lodge in the heart of Windham. Tucked into a quiet wooded setting, this five ...
From $800 per night (USD)VRBO
From $231 per night (USD)Expedia
Whispering River - Catskills New York
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the newly renovated house with central Heating and Cooling located just minutes from skiing, hiking and every ...
From $231 per night (USD)Expedia
From $655 per night (USD)VRBO
Modern A-Frame Cabin 3BR + Loft Luxury Retreat in Windham, NY
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Discover year-round comfort and style at this beautifully designed A-frame cabin just 5 minutes from Windham Mountain an ...
From $655 per night (USD)VRBO
From $255 per night (USD)VRBO
Cozy renovated home, ideal for skiing and hiking in Catskills
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
A recently renovated Dutch farmhouse style house will charm you with its modern yet traditional feel and perfect locatio ...
From $255 per night (USD)VRBO
From $587 per night (USD)VRBO
Luxurious Home & Amazing Views
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Whether you're seeking a peaceful escape or exciting adventure, this luxurious home is the perfect getaway!This ...
From $587 per night (USD)VRBO
From $370 per night (USD)VRBO
Retro Retreat: Charming Home w/Hot Tub & Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Nestled on spacious land just 3 miles from Windham Mt and 12 mins to Hunter Mt, this 1970s ski chalet will prov ...
From $370 per night (USD)VRBO
From $556 per night (USD)VRBO
4 SEASON VACATION RENTAL
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Large four bedroom, two kings beds and two queens beds, 2.5 bathroom country home. All new stainless steel kitchen app ...
From $556 per night (USD)VRBO
From $395 per night (USD)Expedia
Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful Country Setting 3 min to Windham town center w Large deck/ New Hot Tub and Large Wood Fire pit across our b ...
From $395 per night (USD)Expedia
From $1315 per night (USD)VRBO
New Custom Built Catskill Mountain Chalet with Elevator
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 8
This 6 Bedroom, 4 bath chalet is ski in/ski out and directly on the Windham mountainside just a short walk from the base ...
From $1315 per night (USD)VRBO
From $527 per night (USD)VRBO
*GUT RENO 4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*Windhm Mtn View*2BBQs
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Featured in New York Magazine and Awarded as a Top Choice Getaway in Windham, NY the Gem of the Catkills, Upstate New Yo ...
From $527 per night (USD)VRBO
From $775 per night (USD)VRBO
Windham/Hunter All-season French Country Farmhouse-Ultimate in Relaxed Elegance!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
The perfect multi-family get-away. Spend a beautiful holiday in French country comfort! 6- bedrooms, 3 bathrooms, 1 yog ...
From $775 per night (USD)VRBO
From $238 per night (USD)VRBO
Ski, Hike,Bike,Golf, Dine within a 6 min Drive. Perfect for a Family getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Gorgeous, newly renovated, corner unit with L shaped deck,2 bedroom, 2 bath with picturesque views featuring main level ...
From $238 per night (USD)VRBO
From $484 per night (USD)VRBO
Blue Spruce Chalet — Hot Tub, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the charms of an authentic chalet featured in INSIDER in 2022 with breathtaking views, a hot tub, working wood- ...
From $484 per night (USD)VRBO
From $495 per night (USD)VRBO
5 Bedroom Mountain Oasis
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
This cozy 5 bedroom, 5-acre mountain house boasts all the home comforts and amenities plus the charm of the Catskills. T ...
From $495 per night (USD)VRBO
From $540 per night (USD)VRBO
Waterfront Secluded Log-house w/Sauna, Games, More, Mins To Town & Activities
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
This beautiful getaway in the heart of the Catskill mountain region is the perfect oasis for creating memories that will ...
From $540 per night (USD)VRBO
From $807 per night (USD)VRBO
NEW - Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Viridian Lodge is a vacationer’s dream midcentury modern lodge and home away from home. Set on almost 4 acres of land wi ...
From $807 per night (USD)VRBO
From $443 per night (USD)VRBO
Windham/Hunter Chalet with breathtaking views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
We are a friendly family of an architect and interior designer who love sharing our comfortable home with our guests. W ...
From $443 per night (USD)VRBO
From $802 per night (USD)VRBO
All Season Luxury Condo in Windham/ Ski On - Ski Off
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful, brand new four bedroom, four bathroom condo right on the slopes at Windham Mountain in New York's Catskill Mo ...
From $802 per night (USD)VRBO
From $319 per night (USD)VRBO
Close to both Hunter and Windham Mnts
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Spacious townhouse has 2 Bedroom, 2 full baths! The first floor had an open floor plan with a fully-stocked kitchen, ...
From $319 per night (USD)VRBO
From $118 per night (USD)VRBO
Windham NY 2 Bedroom Cozy Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Great little historic rental centrally located in the "Gem of the Catskills," Windham, NY. Family friendly or a cozy li ...
From $118 per night (USD)VRBO
From $189 per night (USD)VRBO
Cozy Windham/Hunter Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Our place is a cozy 2 bedroom apartment on the bottom level of our home with a private entrance, nestled in the northern ...
From $189 per night (USD)VRBO
From $131 per night (USD)VRBO
Catskill Domeo - Romantic Magical Geodesic Glamping Dome in Catskill Mountains
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Catskill Domeo. You will love it so much, it will feel like it is forbidden! ;) Beautiful birch work throughout the ent ...
From $131 per night (USD)VRBO
From $809 per night (USD)VRBO
Modern Mountain House 5Bd/3Ba, HotTub, 4 Season Room, 5 min from Windham Mtn
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
BRAND NEW completely renovated 5 bed/3bath mountain house in Windham, 4 season room, hot tub, gas fireplace, 5 min from ...
From $809 per night (USD)VRBO
From $115 per night (USD)VRBO
Catskill Getaway - Great for Skiers. 2 Miles To Windham Mountain, 6 To Hunter
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Cozy, 1 bedroom apartment, ideal for a couple. 3rd person considered on case to case basis. Beds: 1 full, 1 folding matt ...
From $115 per night (USD)VRBO
From $504 per night (USD)VRBO
\"New Home\" Idyllic Mt Views ,Pond & Horse farm views 2 min to Town
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Beautifully constructed 2019 new home on a property with gorgeous mountain range views and horse farm views. Large open ...
From $504 per night (USD)VRBO
From $477 per night (USD)VRBO
Newly Renovated House ~ Secluded 5 Acre Retreat ~ Peaceful and Quiet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Large house for rent on five + acres with a stream next to the house. Five minutes to Windham ski slopes, ten minutes to ...
From $477 per night (USD)VRBO
From $463 per night (USD)VRBO
Private family home! 4 miles to Windham Mtn!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
The home sits on 5.5 acres surrounded by preserved state land on a dead end, gravel private road, and is the perfect pla ...
From $463 per night (USD)VRBO
From $3780 per night (USD)VRBO
EXCLUSIVE, EXQUISITE & UNFORGETTABLE MOUNTAIN OASIS
- Bedrooms:
- 7
- Bathrooms:
- 9
- Sleeps:
- 18
BOOK YOUR '22-'23 SKI RENTAL NOW! 5-star luxury estate! Only 2 ½ hours from NYC, but light years away from stress. This ...
From $3780 per night (USD)VRBO
From $810 per night (USD)VRBO
Mountain View Chalet Near Skiing
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
THE PROPERTY: Nestled on 3.25 acres of nature's beauty our Catskills retreat, convenient to both Windham and Hunter mou ...
From $810 per night (USD)VRBO
From $348 per night (USD)Expedia
Wonderful mountain home for all of your family adventures!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 15
Welcome to our cozy mountain retreat! Our beautiful and spacious cabin is perfect for your next getaway. Whether you’re ...
From $348 per night (USD)Expedia
From $500 per night (USD)VRBO
Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our charming timber frame home offers a unique aesthetic appeal - a harmonious combination of rustic warmth and modern f ...
From $500 per night (USD)VRBO
From $544 per night (USD)VRBO
Gorgeous Windham Retreat With Views Of The Slopes Only 3 Minutes To Town!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Stunning Windham Log Cabin Retreat! This spacious home has 4 bedrooms and 3 and 1/2 bathrooms. Sleeps 8-10 (1 King, 2 ...
From $544 per night (USD)VRBO
From $1822 per night (USD)VRBO
Windham Log Cabin on 35 Acres. Family friendly.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
5300 square foot house on 35 acres with views of the Western Catskills. The house sits on a 20 acre parcel with 5 Acres ...
From $1822 per night (USD)VRBO
From $929 per night (USD)VRBO
Luxury 4BR/4BA Ski-In / Ski-Out Mountain Stay \"The Four Ski-sons\"
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Luxury Ski-on and off from trail side! Beautiful accommodations to relax, unwind, ski, hike, bike, golf, horseback ride, ...
From $929 per night (USD)VRBO
From $410 per night (USD)VRBO
Windham Mountain Ski House with great views of Windham and the Valley.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Great views of Windham Mountain and the valley left and right. The house is 1.3 miles from Ski Windham. Large living roo ...
From $410 per night (USD)VRBO
From $211 per night (USD)VRBO
4BR TOWNHOUSE MINUTES TO WINDHAM & HUNTER\nFree shuttle to Windham Mnt ski season
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Crystal Pond Complex | 1,700 Sq Ft | Windham Mountain Shuttle stops right in front of the building! 12min drive to Hun ...
From $211 per night (USD)VRBO
From $1071 per night (USD)VRBO
Tuscan Year Round Beauty - Pickleball Court
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Among the nicest properties in Windham. Lovely large home nestled quietly on 12 usable acres with bucolic bridle paths j ...
From $1071 per night (USD)VRBO
From $1760 per night (USD)Expedia
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
- Bedrooms:
- 5
- Bathrooms:
- 9
- Sleeps:
- 30
The Lodge at Dancing Horse Farm is set on an historic farmstead with beautiful mountain views and is just minutes away f ...
From $1760 per night (USD)Expedia
From $693 per night (USD)VRBO
5-Star. Luxury Condo, Heated Pool, Hot Tub, Ski in/out @ Windham
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This is a one-of-a-kind ski rental and the first rented in 2019. It is 3 Bedrooms + Den (sleep sofa) and 4 full bathroo ...
From $693 per night (USD)VRBO
From $341 per night (USD)VRBO
Hunter/Windham Area - Winter Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Three bedroom ground floor apt close to Hunter Mountain and Windham Mountain in the Catskills in upstate New York.— slee ...
From $341 per night (USD)VRBO
From $477 per night (USD)VRBO
Near Hunter and Windham ski resorts. Crystal Pond town house, 4BR & 3.5 bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This is our family's home away from home. We mostly use it in the summer and once in a while for skiing. Having kids who ...
From $477 per night (USD)VRBO
From $342 per night (USD)Expedia
Windham Immaculate Ski Chalet with Awesome Fire Pit.\nAvailable 25/26 Ski Season!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Available for Season 25/26 Ski Season! $15,000. Nov 15, 2025 - April 15, 2026 Ultra Clean, Modern, Close to Windham Moun ...
From $342 per night (USD)Expedia
From $441 per night (USD)VRBO
Windham- Newly Renovated 4 BR Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy our newly renovated home located less than 5 minutes from Windham Mountain and less than 15 minutesto Hunter mount ...
From $441 per night (USD)VRBO
From $160 per night (USD)VRBO
Simply Amazing Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Amazing 2 Bedroom, 2 Bathroom Condo just minutes away Windham Mountain, hiking trails, shops and great restaurants. that ...
From $160 per night (USD)VRBO
From $1001 per night (USD)VRBO
Amazing Mountain View’s from every room! Hot Tub/3 Fire pits & Game Rm
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
The highest Mountain View’s with Ski Windham as well as Hunter Mountain ski slope views and Valley Views . A breathtakin ...
From $1001 per night (USD)VRBO
From $605 per night (USD)Expedia
Mid Century Modern Chalet with Tennis Court and Catskill Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Mid-century modern chalet featuring large windows with great views, soaring ceilings, exposed wood beams, huge fireplace ...
From $605 per night (USD)Expedia
From $804 per night (USD)VRBO
Mountain Escape: 5BR Chalet | 6 Min to Ski Resort
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
Experience the allure of this 3300 sq ft chalet boasting 5 bedrooms and 4 baths, ideally situated directly across from W ...
From $804 per night (USD)VRBO
From $281 per night (USD)Expedia
Mtn-View Home w\/ Deck on 4 Acres in Windham
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
5 Mi to Windham Mountain Club | Remote Workers Welcome Tucked away in the heart of Windham, this 3-bedroom, 2-bath vac ...
From $281 per night (USD)Expedia
From $1377 per night (USD)VRBO
Reduced May Rates - Plus Special Culinary Promotion! Details Below!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Reduced May Rates - Plus Special Culinary Promotion! Details Below! Breathtaking Design, Newly Constructed Farmhouse wit ...
From $1377 per night (USD)VRBO
From $810 per night (USD)Expedia
Woodside Cabin #2 on Lake Heloise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 18
Charming cabin to stay and play in at the lake. Have fun swimming and fishing on the lake. This property was a campsite ...
From $810 per night (USD)Expedia
From $427 per night (USD)VRBO
MIRROR CABIN IN THE FOREST WITH HOT TUB
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Haus Windham - 2 hours from NYC! ➤ Escape to our serene mirror Glass-Walled cabin nestled in the forested mou ...
From $427 per night (USD)VRBO
From $690 per night (USD)Expedia
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to our newly renovated 5-bedroom, 4.5-bathroom farmhouse located 3 minutes from the heart of Windham, NY, where ...
From $690 per night (USD)Expedia
From $1005 per night (USD)VRBO
Brand NEW MINT Windham 5BR/4.5BA home on 5 acre, wooded hilltop.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
MINT 5BR, 4.5BA, brand new home. Full modern furnishing complete 5/1. Panoramic views from 5 acre hilltop with forest ba ...
From $1005 per night (USD)VRBO
From $1377 per night (USD)Expedia
Reduced May Rates - Plus Special Culinary Promotion! Details Below!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Reduced May Rates - Plus Special Culinary Promotion! Details Below! Breathtaking Design, Newly Constructed Farmhouse wit ...
From $1377 per night (USD)Expedia
From $540 per night (USD)VRBO
Mountain Chalet with Hot Tub, Ski, & Amazing Views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
*New Listing Discount applied to all bookings made before 5/30/25!!* Chalet retreat in Hensonville, nestled convenientl ...
From $540 per night (USD)VRBO
From $261 per night (USD)Expedia
Ski, Hike & Golf: Pet-Friendly Windham Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
2 Mi to Windham Mountain Club | Furnished Deck | Peaceful, Wooded Surroundings | Fireplace Surrounded by lush woodlands ...
From $261 per night (USD)Expedia
From $172 per night (USD)VRBO
Country Room. Cozy room with a Queen-Size bed, en-suite bathroom, and FREE breakfast. Sleeps 2.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You're booking the smallest room at Mountain Treasure Bed and Breakfast. Other amenities in this room include: -QUEEN S ...
From $172 per night (USD)VRBO
From $205 per night (USD)Expedia
Americana Room. Elegant room with a King-Size bed, en suite bathroom, and mountain views. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Americana Room is located on the second floor of Mountain Treasure Bed and Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You're booking one room at Mountain Treasure Bed and Breakfast. Other amenities in this room include: -KING Size Bed wit ...
From $205 per night (USD)Expedia
From $172 per night (USD)VRBO
Art Nouveau Room<br>Large room decorated in the Art Nouveau style with FULL-size bed, en suite bathroom.FREE breakfast. Sleeps 2.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You're booking one room at Mountain Treasure Bed and Breakfast. Other AMENITIES in this room include: -FULL-Size Bed wit ...
From $172 per night (USD)VRBO
From $1818 per night (USD)VRBO
LUXURIOUS & SERENE SKI-IN/ SKI-OUT \"Winterfell\" LODGE
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to an unparalleled luxury living experience at this exquisite post-and-beam, charming **Ski-in/ Ski-Out, lodge o ...
From $1818 per night (USD)VRBO
From $1278 per night (USD)VRBO
Ski-in, Ski-out GORGEOUS mountain chalet in prime location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful wood and stone chalet directly off a green level ski/summer bike or hike run close to base of Windham mountain ...
From $1278 per night (USD)VRBO
From $1449 per night (USD)Expedia
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. 5 min from Windham Ski
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Black Bear Cabin: Your Luxurious Mountain Retreat Luxury 3,300 sqft Ski and Golf Chalet with 4 bedrooms + 4 ensuite bat ...
From $1449 per night (USD)Expedia
From $589 per night (USD)VRBO
Beautiful Catskills country retreat --neighboring reservoir/recreation area
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
The dancing bear welcomes you to our beautiful, fully restored, 1800’s farmhouse on 5 acres of woods and a large grass y ...
From $589 per night (USD)VRBO
From $593 per night (USD)VRBO
Spacious Mountain Escape - Minutes to Windham/Hunter
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Spacious, light-infused contemporary on park-like grounds just minutes from Windham and Hunter ski areas. Multiple wood ...
From $593 per night (USD)VRBO
From $540 per night (USD)VRBO
5BDR Cozy Windham Mountain Escape - Close to Skiing and Hiking!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to the Windham Mountain Escape! With 2 private units it is the perfect getaway for multiple families traveling t ...
From $540 per night (USD)VRBO
From $506 per night (USD)Expedia
Windham castle with a view & minutes to skiing!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 11
Great retreat for enjoying time with families and friends. The whole group will be comfortable in this spacious and uniq ...
From $506 per night (USD)Expedia