Windham Rentals
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 $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 $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 $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 $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 $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 $442 per night (USD)VRBO
Windham Mountain A Frame Ski House with Central A\/C
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Classic A Frame Retreat only 2 miles from ski windham on private 5 acre lot with new cental A/C. This extra large clean ...
From $442 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 $992 per night (USD)Expedia
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)Expedia
From $248 per night (USD)VRBO
Guesthouse Minutes from the Mountain!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to our charming guest house, nestled just minutes away from Windham Mountain! This cozy retreat offers ...
From $248 per night (USD)VRBO
From $796 per night (USD)VRBO
Luxurious Home & Amazing Views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Whether you're seeking a peaceful escape or exciting adventure, this luxurious home is the perfect getaway!This ...
From $796 per night (USD)VRBO
From $593 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 $593 per night (USD)VRBO
From $859 per night (USD)VRBO
Chalet nestled right in Windham Mountain's quiet beauty-private access to trails
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
*STILL TIME TO BOOK SKI SEASON 2024-25! SUMMER RATES NOW THROUGH AUGUST** Perfect Windham Mountain slope side chalet ...
From $859 per night (USD)VRBO
From $1848 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 $1848 per night (USD)VRBO
From $1018 per night (USD)VRBO
Summer at Windham Mountain! On mountain 5 bedroom Retreat!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 22
This 2000 foot home boasts 5 bedrooms and 3 1/2 bathrooms. During the winter you can walk to skiing and the adventure pa ...
From $1018 per night (USD)VRBO
From $390 per night (USD)VRBO
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 $390 per night (USD)VRBO
From $638 per night (USD)Expedia
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)Expedia
From $273 per night (USD)VRBO
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)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 $628 per night (USD)VRBO
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)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 $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 $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 $400 per night (USD)VRBO
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)VRBO
From $2550 per night (USD)Expedia
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)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 $258 per night (USD)Expedia
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)Expedia
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 $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 $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 $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
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 $285 per night (USD)Expedia
Newly Built 1200sq ft Guest House 4min to Ski & Hiking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful newly built 1200 sq ft cozy log guest house, w vaulted ceiling’s and a gas fireplace for a charming indoor exp ...
From $285 per night (USD)Expedia
From $839 per night (USD)VRBO
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)VRBO
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 $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 $700 per night (USD)VRBO
\"Three Pines\" Luxury 6 Bedroom Ski Chalet with Windham Views
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
This house was built from the ground up and has never been rented. you could be the first! Situated on five private acre ...
From $700 per night (USD)VRBO
From $1101 per night (USD)VRBO
4 Bdrm Home w\/Hot Tub + Mtn. Views @Hotel Vienna
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Located on the grounds of Hotel Vienna, this gorgeous 4 bedroom log home with Hot Tub and Incredible Mountain views is a ...
From $1101 per night (USD)VRBO
From $2020 per night (USD)Expedia
Contemporary Renovated Retreat with Mountain Views, Spacious Living Spaces...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Windham Mountainside Marvel Contemporary Renovated Retreat with Mountain Views, Spacious Living Spaces with Bluestone F ...
From $2020 per night (USD)Expedia
From $357 per night (USD)VRBO
4-bedroom mountain getaway in the Catskills located just nearby Windham Mountain
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to our cozy mountain getaway in the Catskills! Only a 3-minute drive from Windham Mountain and Windham Country C ...
From $357 per night (USD)VRBO
From $1051 per night (USD)VRBO
Bump Mountain Retreat: Hot Tub, Sauna, Pool, Game Room, Piano & Panoramic Views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
If you're looking for a luxurious ski retreat a short drive from NYC, then look no further. Perched on a mountainside, B ...
From $1051 per night (USD)VRBO
From $604 per night (USD)VRBO
Luxury Ski-in Ski-Out Condo @ Windham Mountain
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This Whisper Creek condo is located in the newest luxury building at Windham, with a heated outdoor swimming pool, two h ...
From $604 per night (USD)VRBO
From $1781 per night (USD)VRBO
Windham ski in-out condo, luxury 2000+ sf modern 5BR, hot tub, pool, boot room++
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
We are renting our 2000+ sf modern, renovated, mountain facing luxury condo at Whisper Creek to someone who will take gr ...
From $1781 per night (USD)VRBO
From $293 per night (USD)VRBO
Vacation Rental Home ~ 2 Mi to Windham Mountain!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Discover the charming town of Windham, NY, and stay at this spacious 3-bedroom, 1.5-bath vacation rental. With a cozy fi ...
From $293 per night (USD)VRBO
From $1140 per night (USD)VRBO
Lux Mansion Windham, Catskills Hot Tub, BBQ, Pool Table, Fire pit, Pond
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
SPECIAL OFFER until the end of December! Book 2 nights on weekdays and get 50% off the 3rd night (weekdays only) <b>We ...
From $1140 per night (USD)VRBO
From $996 per night (USD)VRBO
Ski-in \/ Ski-out luxury 3-bedroom Windham condo with outdoor pool and hot-tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Get ready to relax in this 3-bedroom condo in Windham. With 2 king beds and 2 bunk beds, guests will have plenty of spac ...
From $996 per night (USD)VRBO
From $843 per night (USD)Expedia
Brand New Luxury Ski Cabin - 2 Mi to Windham Mtn!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Witness the breathtaking beauty of the Catskill Mountains at this stunning 6-bed, 5.5-bath vacation rental. Nestled in n ...
From $843 per night (USD)Expedia
From $476 per night (USD)VRBO
PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $476 per night (USD)VRBO
From $266 per night (USD)Expedia
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $266 per night (USD)Expedia
From $332 per night (USD)VRBO
LUXURY DUPLEX SUITE WITH JACUZZI
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $332 per night (USD)VRBO
From $251 per night (USD)Expedia
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Step inside and be greeted by a haven of sophistication. The living area boasts a stunning fireplace, casting a warm and ...
From $251 per night (USD)Expedia
From $561 per night (USD)VRBO
GLASS MIRROR CABIN - HAUS WINDHAM
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $561 per night (USD)VRBO
From $388 per night (USD)Expedia
The Haüs Windham - Luxury 2 Bedroom Suite w Loft
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $388 per night (USD)Expedia
From $615 per night (USD)VRBO
Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This is a beautiful log home on 8 acres with amazing views of Windham Mountain. The home is made of Canadian pine logs t ...
From $615 per night (USD)VRBO
From $1207 per night (USD)VRBO
'Sundance Vistas - Log Home ' - 2 Miles From Windham Ski Mountain
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Canadian Log Home on 14 acres yet only 2 miles to Windham Ski Mountain. The house has 4 bedrooms plus a loft and 3 bat ...
From $1207 per night (USD)VRBO
From $1156 per night (USD)VRBO
5 Bedrooms 5 1\/2 Bath Ski Area Views, Walk to Skiing, Huge Common Space & Decks!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Unit 3: This brand new 3600 square foot townhome boasts 5 bedroom and 5 1/2 baths directly across from Windham Mountain. ...
From $1156 per night (USD)VRBO
From $784 per night (USD)VRBO
\nStunning Chalet style home in Catskills with 8 Person hot tub, fire pit & Sauna
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Brand new four bedroom cozy log home (Chalet style) nestled on 4 acres on a quiet mountain road. Easily sleeps 10 pe ...
From $784 per night (USD)VRBO
From $3111 per night (USD)VRBO
Luxurious ski in\/out, 3-story chalet directly on the slopes of Windham Mountain
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 12
Luxurious ski in/ ski out, three-story chalet located directly on the slopes of Windham Mountain and minutes drive from ...
From $3111 per night (USD)VRBO
From $625 per night (USD)VRBO
Great Location - Ski In Ski Out Condo+Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Enclave condo building is equipped with a heated outdoor swimming pool, two hot tubs, gym, a patio with a fire pit w ...
From $625 per night (USD)VRBO
From $1080 per night (USD)VRBO
40 acres. seasonal rental.Mountain views.sleeps 12+.perfect for 2 families.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
This sprawling, jaw-dropping 40-acre estate will leave you and your guests speechless. It is often regarded as the prem ...
From $1080 per night (USD)VRBO
From $1168 per night (USD)VRBO
Seasonal Pool Plus Hot Tub & EV Charger 5 mins to Skiing at Windham Mountain
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
**Our brand new 30x8 shipping container pool, just completed in August of 2024, is available in the summer months and p ...
From $1168 per night (USD)VRBO