Town of Windham Rentals
- From $1200 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 $1200 per night (USD)VRBO
- From $317 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 $317 per night (USD)VRBO
- From $463 per night (USD)
VRBO
Retreat mountain home
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Fully furnished, very comfortable, open living space. Property situated on 10+ beautiful acres in the Catskill mountains ...
From $463 per night (USD)VRBO
- From $926 per night (USD)
VRBO
HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to a wonderful oasis of tranquility. Beautiful bright A-frame home sited on 10 secluded private acres with open ...
From $926 per night (USD)VRBO
- From $114 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 $114 per night (USD)VRBO
- From $662 per night (USD)
VRBO
Year-Round Relaxing Mountain Escape
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
Luxury 6 Bedroom year-round retreat nestled in secluded pine forest. Large open floor plan with vaulted ceilings great f ...
From $662 per night (USD)VRBO
- From $208 per night (USD)
VRBO
Relax!! Escape the city!! Updated condo w Mtn views from deck w\/ turbo internet
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Chic, spacious updated two level corner unit townhouse. Freshly painted a serene light gray, brand new barn wood floorin ...
From $208 per night (USD)VRBO
- From $492 per night (USD)
VRBO
with Secluded Fire Pit\nUltra Clean, Modern, Close to Windham Mountain.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Available for Season Rental 24/25 Ski Season! $14,000 This home is a super immaculate, upscale, classic ski chalet nestl ...
From $492 per night (USD)VRBO
- From $712 per night (USD)
VRBO
Windham Townhouse - Base of Mountain
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Base of Windham, Large 3 bedroom town home. Please remember to check WindhamMountain.com Ski Season & Bike Park update ...
From $712 per night (USD)VRBO
- From $174 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 $174 per night (USD)VRBO
- From $140 per night (USD)
VRBO
Catskill Domeo - Romantic Magical Geodesic Glamping Dome in Catskill Mountains
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Catskill Domeo. You will love it so much, it will feel like it is forbidden! ;) Beautiful birch work throughout the ent ...
From $140 per night (USD)VRBO
- From $1361 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 $1361 per night (USD)VRBO
- From $123 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 $123 per night (USD)VRBO
- From $596 per night (USD)
VRBO
VINTAGE ART WINDHAM HOUSE WITH BAR, HOT TUB, FIREPLACE 5 MIN TO SKI
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
WELCOME TO THE WINDHAM ART HOUSE WITH BRAND NEW HOT TUB, OUTDOOR SWIMMING POOL, WALL-TO-WALL WOOD FIREPLACE, HANDMADE BA ...
From $596 per night (USD)VRBO
- From $575 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 $575 per night (USD)VRBO
- From $1236 per night (USD)
VRBO
Steps away from the magic carpet that brings you right to the lodge!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy beautiful mountain views while soaking in the hot tub after a great day on the slopes! This townhouse is convenien ...
From $1236 per night (USD)VRBO
- From $909 per night (USD)
VRBO
5-Star Lux Condo, Heated Pool, Hot Tub, Ski in\/out @ Windham
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
All of the furniture, linens and amenities are brand new! We are at the base of the mtn and it is ski in/out -- perfec ...
From $909 per night (USD)VRBO
- From $2410 per night (USD)
VRBO
5 Min to Windham Mtn! Luxury Retreat w\/ Mountain Views! Natural Swimming Pond
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 22
Welcome to the Mountain House. Sitting on five beautiful acres with views of 4 of the highest peaks in the Catskills, r ...
From $2410 per night (USD)VRBO
- From $429 per night (USD)
VRBO
Cozy townhouse steps away from Windham Mountain- zip code 12496
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
Note: When making vacation reservations, please plan ahead by including lift tickets in your purchase – advanced purchas ...
From $429 per night (USD)VRBO
- From $3571 per night (USD)
VRBO
EXCLUSIVE, EXQUISITE & UNFORGETTABLE MOUNTAIN OASIS
- Bedrooms:
- 8
- 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 $3571 per night (USD)VRBO
- From $619 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 $619 per night (USD)VRBO
- From $397 per night (USD)
VRBO
Catskill MTN House w\/ Hot Tub and Large Outdoor Decks, fire-pit, close to hiking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Cozy updated house located close to the Elm Ridge Trail System, Windham Mountain (7 min), Hunter Moutain (15 min) and do ...
From $397 per night (USD)VRBO
- From $408 per night (USD)
VRBO
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 $408 per night (USD)VRBO
- From $441 per night (USD)
Expedia
Newly Renovated House ~ Secluded 5 Acre Retreat ~ Peaceful and Quiet
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $441 per night (USD)Expedia
- From $429 per night (USD)
VRBO
Private family home! 4 miles to Windham Mtn!
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $429 per night (USD)VRBO
- From $490 per night (USD)
Expedia
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 $490 per night (USD)Expedia
- From $634 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 $634 per night (USD)VRBO
- From $471 per night (USD)
VRBO
Windham Mountain Village - Walk to Slopes - 2 Bedroom\/2 Bathroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Amazing location, 2 Bedroom / 2 Bathroom Condo in Windham Mountain Village, walk to the slopes. The unit has a king bed ...
From $471 per night (USD)VRBO
- From $1800 per night (USD)
VRBO
Windham Log Cabin on 35 Acres. Family friendly.
- Bedrooms:
- 5
- 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 $1800 per night (USD)VRBO
- From $482 per night (USD)
VRBO
4BR TOWNHOUSE MINUTES TO WINDHAM & HUNTER\nFree shuttle to Windham Mnt ski season
- Bedrooms:
- 4
- 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 $482 per night (USD)VRBO
- From $1162 per night (USD)
VRBO
Luxury Home on Windham Mountain! Walk to Slopes
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Come enjoy the finest that Windham Mountain has to offer in this spacious, contemporary ski home with breath-taking moun ...
From $1162 per night (USD)VRBO
- From $538 per night (USD)
VRBO
SKI Slope views, ski 1 mile drive or walk, Golf Course & walk to town.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy one family Colonial/cape style home, with beautiful stone front furnished porch w/BBQ. Full view of Ski Windham Mou ...
From $538 per night (USD)VRBO
- From $745 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 $745 per night (USD)VRBO
- From $355 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 $355 per night (USD)VRBO
- From $625 per night (USD)
VRBO
5 Minutes To Windham Slopes! High End Amenities! Entertainment Galore!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This home is approximately 2000square feet of modern amenities with front door views of the windham slopes. The main lev ...
From $625 per night (USD)VRBO
- From $508 per night (USD)
VRBO
Near Hunter and Windham ski resorts. Crystal Pond town house, 4BR & 3.5 bath
- Bedrooms:
- 4
- 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 $508 per night (USD)VRBO
- From $992 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 $992 per night (USD)VRBO
- From $1206 per night (USD)
Expedia
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
- Bedrooms:
- 5
- Bathrooms:
- 10
- 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 $1206 per night (USD)Expedia
- From $235 per night (USD)
VRBO
2 Bedroom Townhouse in front of Windham Mountain Ski Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This 2 bedroom, 2 bath Townhouse with loft is located at the top of Windham Mt Village a very short easy walking distanc ...
From $235 per night (USD)VRBO
- From $434 per night (USD)
Expedia
Windham Immaculate Ski Chalet with Awesome Fire Pit.\n\n\n
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Available for Season 24/25 Ski Season! $15,000. Nov 15, 2024 - April 15, 2025 Ultra Clean, Modern, Close to Windham Moun ...
From $434 per night (USD)Expedia
- From $140 per night (USD)
VRBO
Studio 3 BEDS-SLEEPS 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
HIDDEN GEM IN CATSKILLS. Relax in the fresh mountain air! Light-filled cozy studio on Main St in downtown Windham. S ...
From $140 per night (USD)VRBO
- From $379 per night (USD)
VRBO
Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Alpine Escape! Enjoy incredibly easy access to some of the best skiing in New York. This home has all the e ...
From $379 per night (USD)VRBO
- From $1373 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 $1373 per night (USD)VRBO
- From $355 per night (USD)
VRBO
Windham Mountain Ski House with great views of Windham and the Valley.
- Bedrooms:
- 2
- Bathrooms:
- 5
- 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 $355 per night (USD)VRBO
- From $4367 per night (USD)
VRBO
Luxury Mountain Log Home, Ski-In\/Ski-Out to Windham Resort
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 22
* NOTE: Your safety matters. The property features exterior surveillance cameras surrounding the home; these do not look ...
From $4367 per night (USD)VRBO
- From $406 per night (USD)
Expedia
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled on three acres of land with a panoramic view of the Catskill Mountain the Mountain Treasure Two-Bedroom Cottage ...
From $406 per night (USD)Expedia
- From $638 per night (USD)
VRBO
Panoramic views four minutes to Windham Mountain skiing.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to the Windham Round Haus located just minutes from Windham Mountain. Our home is located on a private street a ...
From $638 per night (USD)VRBO
- From $219 per night (USD)
Expedia
Quiet basement apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This is a two bedroom basement apartment with a fireplace and hot tub Off street parking firewood plowing included Th ...
From $219 per night (USD)Expedia
- From $980 per night (USD)
VRBO
Amazing Mountain View’s from every room! Hot Tub\/3 Fire pits & Game Rm
- Bedrooms:
- 4
- 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 $980 per night (USD)VRBO
- From $703 per night (USD)
Expedia
Vintage Charm Farmhouse Retreat
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Come and enjoy the mountains all year round! This Farmhouse is conveniently located within minutes from Windham and Hunt ...
From $703 per night (USD)Expedia
- From $1588 per night (USD)
VRBO
7 Bedroom Luxurious Chalet In Windham, NY
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
Welcome to our Catskill getaway located in the town of Windham sitting on 7.5 acres. Our 7 bedroom house is all about sl ...
From $1588 per night (USD)VRBO
- From $437 per night (USD)
Expedia
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 $437 per night (USD)Expedia
- From $560 per night (USD)
VRBO
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 $560 per night (USD)VRBO
- From $273 per night (USD)
Expedia
Windham Mountain Vacation Rental ~ 3 Mi to Lifts!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Find your next all-season escape at this lovely Catskills vacation rental! Located less than 5 miles from Windham Mounta ...
From $273 per night (USD)Expedia
- From $515 per night (USD)
VRBO
Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Tucked away in the forest just a day trip from NYC, you'll find this gem of a mountain retreat where outdoor adventure a ...
From $515 per night (USD)VRBO
- From $392 per night (USD)
Expedia
NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $392 per night (USD)Expedia
- From $705 per night (USD)
VRBO
The Hensonville Honeypot - 2mins walking distance to local town cafes and shops.
- Bedrooms:
- 5
- 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 $705 per night (USD)VRBO
- From $628 per night (USD)
Expedia
NEW OUTDOOR HOT TUB!! 5 BEDROOM\/3 BATH CHALET - HAUS WINDHAM
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $628 per night (USD)Expedia
- From $540 per night (USD)
VRBO
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to this newly renovated mountain cabin just 5 minutes from Windham Mountain ski resort! With a private fishing po ...
From $540 per night (USD)VRBO
- From $719 per night (USD)
Expedia
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 $719 per night (USD)Expedia
- From $634 per night (USD)
VRBO
Windham Luxury Pet Friendly Retreat.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 11
New log-style home fully furnished on 3 levels; family rooms on the 1st and 2nd levels; lower level radiant heated tile ...
From $634 per night (USD)VRBO
- From $3387 per night (USD)
Expedia
Spacious 6-bedroom cabin in cool Windham with AC, WiFi
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
This Windham cabin boasts 6 inviting bedrooms, including 1 king bed, 4 queen beds, and 3 bunk beds. With amenities like ...
From $3387 per night (USD)Expedia
- From $258 per night (USD)
VRBO
2 Mi to Windham Mountain: Scenic Home w\/ Fire Pit!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Updated Interior w/ Modern Decor & Appliances | Office w/ Dedicated Workspace & Large Windows | Pet Friendly w/ Fee Qui ...
From $258 per night (USD)VRBO
- From $1107 per night (USD)
Expedia
Welcome to our home in the mountains, 2 hrs from NYC. 6BR, sleeps 12. Ski in\/out
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to our home in the mountains, 2 hrs from NYC. 6BR, 5.5 bathrooms. sleeps 12 people - hot tub and some great vie ...
From $1107 per night (USD)Expedia
- From $1465 per night (USD)
VRBO
Custom Windham Mtn Villa w\/ Pool, Theater & Views!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
The poster child for a 'dream house,' this stunning 5-bedroom, 4.5-bath vacation rental is sure to be adored by luxury t ...
From $1465 per night (USD)VRBO
- From $961 per night (USD)
Expedia
NEW Modern Cabin | 8 Mins From Skiing | Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Sophie’s Summit Lodge is located in the heart of the Catskills in historic Windham, NY. Our 5 BD and 5 BA cabin features ...
From $961 per night (USD)Expedia
- From $1574 per night (USD)
VRBO
Modern Ski-View Pool House: Contemporary Comfort in Windham, New York
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to our inviting ski-view getaway in Windham, New York! Perched on the slopes, this vrbo promises a ski enthusias ...
From $1574 per night (USD)VRBO
- From $1438 per night (USD)
VRBO
Luxurious Penthouse with Full Mountain Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
High-end ski-in/ski-out condo located steps away from Whisper Run on Windham Mountain fully-appointed with top notch fur ...
From $1438 per night (USD)VRBO
- From $1312 per night (USD)
VRBO
Windham Mountain ski on\/off 3br condo. Pool, Common areas, boot room and gym!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Discover this meticulously maintained true ski on/off 3 BR 3 full bath gem at Windham Mountain Club. Located in the cove ...
From $1312 per night (USD)VRBO
- From $228 per night (USD)
Expedia
Mtn-View Home w\/ Deck on 4 Acres in Windham
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $228 per night (USD)Expedia
- From $1129 per night (USD)
VRBO
Fully updated townhome 200 feet from slopes of Windham Mountain
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This 3-bedroom 3 bath townhome 200 feet from the Windham ski lift is perfect for your escape. With a king bed, 2 bunk be ...
From $1129 per night (USD)VRBO
- From $1295 per night (USD)
Expedia
5-Bedroom Luxury Home on 7 Secluded Acres (10min from Windham Mountain)
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Enjoy a day on the slopes or hiking, followed by a hot tub for sore muscles, wine by the fire, or a movie in the games r ...
From $1295 per night (USD)Expedia
- From $792 per night (USD)
VRBO
Breathtaking Design, Newly Constructed Farmhouse with Wooded Views in Windham NY
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Brand-new construction! Modern farmhouse offers the perfect blend of beauty & peace of the mountains, and the luxurious ...
From $792 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Beautiful Windham Chalet 2 minutes to Town and the Mountain
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Beautiful Chalet with a host of year-round activities! Close to skiing, snowboarding, sledding, snowshoeing, mountain bi ...
From $400 per night (USD)Expedia
- From $2550 per night (USD)
VRBO
6-bedroom SKI Off Chateau at Windham Mountain Club with WiFi
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
Escape to this superb 6-bedroom Ski Off Chateau at Windham Mountain Club and enjoy Apres-Ski Each room of this Smart ho ...
From $2550 per night (USD)VRBO
- From $598 per night (USD)
Expedia
Spacious 5-bedroom house in marvelous Windham with AC, WiFi & wood burning stove
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Experience the Catskills at The Quad Six, a spacious 5-bedroom, 2-bathroom vacation home in Windham, NY. Located near bo ...
From $598 per night (USD)Expedia
- From $1860 per night (USD)
VRBO
LUXURIOUS & SERENE SKI-IN\/ SKI-OUT \"Winterfell\" LODGE
- Bedrooms:
- 7
- 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 $1860 per night (USD)VRBO
- From $1271 per night (USD)
VRBO
Ski-in, Ski-out GORGEOUS mountain chalet in prime location
- Bedrooms:
- 4
- 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 $1271 per night (USD)VRBO
- From $546 per night (USD)
VRBO
Beautiful Catskills country retreat --neighboring reservoir\/recreation area
- Bedrooms:
- 3
- 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 $546 per night (USD)VRBO
- From $656 per night (USD)
Expedia
~ Alpine 5BR Chalet: 6 min to SKI | Sleeps 20 ~
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 20
Experience the allure of this 3300 sq ft chalet boasting 5 bedrooms and 4 baths, ideally situated directly across from W ...
From $656 per night (USD)Expedia
- From $640 per night (USD)
VRBO
Logtastic cabin in Windham with Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
About this space Spacious authentic log cabin on a private serene 6 acres. This cabin has it all...large hot tub, game r ...
From $640 per night (USD)VRBO
- From $522 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 $522 per night (USD)VRBO
- From $490 per night (USD)
VRBO
Ski house just steps from slopes with indoor pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Come enjoy the fall and winter at this great Windham Mountain townhome at the base of Windham Mountain. Space includes 4 ...
From $490 per night (USD)VRBO
- From $240 per night (USD)
VRBO
Big Hollow Board and Batten House with Nerf Treehouse!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Come enjoy the Catskills! Nestled directly between Windham and Hunter Ski Mountains. Hiking trails a mile down the dead- ...
From $240 per night (USD)VRBO
- From $646 per night (USD)
VRBO
Spacious Mountain Escape - Minutes to Windham\/Hunter
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Spacious, light-infused contemporary on park-like grounds just minutes from Windham and Hunter ski areas. Multiple wood ...
From $646 per night (USD)VRBO
- From $1811 per night (USD)
VRBO
Condo on Windham Mountain - Greene County
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful, newly renovated three bedroom, three bathroom condo right on the slopes at Windham Mountain in New York's Cat ...
From $1811 per night (USD)VRBO
- From $2019 per night (USD)
VRBO
*The View* ski in\/out modern luxury at Windham Mountain Resort
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 14
The View is a spectacular new house at the top of Windham Mountain. Ease of ski in/out with all the amenities, from expa ...
From $2019 per night (USD)VRBO
- From $463 per night (USD)
VRBO
Escape to the mountains on 5 acres, 5 minutes to Windham Resort w\/ all Amenities
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Just a 2.5-hour drive from NYC, you can escape to a relaxing, newly built and furnished modern cabin on five acres of wo ...
From $463 per night (USD)VRBO
- From $657 per night (USD)
VRBO
2 Bed Ski-In\/Out Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our 2 bedroom, 2 bath, ski-in/ski-out condo, located at the base of Windham Mountain! This getaway holds 2 co ...
From $657 per night (USD)VRBO
- Click For Pricing
Expedia
Fantastic 2 family vacation home with EV charger
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The perfect luxury vacation gettaway! Fully equipped with everything you need to relax after a day out. Minutes from Win ...
Click For PricingExpedia
- From $1836 per night (USD)
VRBO
Rare Ski-In\/Ski-Out Townhome! Windham Mountain at your back door!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
The rare opportunity to rent an Enclave Townhome is here! Stay in one of the most sought-after locations at the base of ...
From $1836 per night (USD)VRBO
- From $839 per night (USD)
Expedia
Ski Ridge Golf farmhouse
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Relax in this beautiful natural setting course that Windham has to offer, while at the same time enjoying all comforts o ...
From $839 per night (USD)Expedia
- From $749 per night (USD)
VRBO
Bucolic privacy with Hot Tub in Windham
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
The Blue House is a beautiful large home nestled in the gem of the Catskills, Windham - just 5 minutes to restaurants an ...
From $749 per night (USD)VRBO
- From $262 per night (USD)
Expedia
Rustic Mountain view Cabin 5 mins to Ski Area!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Steps from the Mountain! Just 1 mile away with a crisp mountain view, our beautiful chalet is a mere 5 minute drive from ...
From $262 per night (USD)Expedia
- From $254 per night (USD)
VRBO
Windham getaway!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perfectly cozy destination in the mountains for a weekend getaway or a family vacation. This condo has everything that y ...
From $254 per night (USD)VRBO
- From $540 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 $540 per night (USD)Expedia
- From $383 per night (USD)
VRBO
Windham family ski home, walking distance to trails and base
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wake up with a coffee and walk out onto Windham mountain. Enjoy an updated home with a modern kitchen and amenities. A C ...
From $383 per night (USD)VRBO
- From $298 per night (USD)
Expedia
Spacious Townhouse minutes from Village and Slopes with shuttle to mountain
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Spacious 3-Bedroom Townhouse with Sleeping Loft and Wood-Burning Fireplace at Windham Ski Mountain, Min ...
From $298 per night (USD)Expedia
- From $460 per night (USD)
VRBO
Cozy Cabin Getaway in Windham Catskill Mountains\n
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Welcome! You are viewing our cozy 3500-square-foot cabin tucked away on 5.80 acres in the beautiful and scenic hills of ...
From $460 per night (USD)VRBO
- From $675 per night (USD)
Expedia
Stunning A Frame Chalet, Game Rm, 5 min Windham Mt\n\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to our exquisite Chalet, nestled in the heart of natural beauty, where relaxation and sophistication blend to cr ...
From $675 per night (USD)Expedia