Maplecrest Unit Rentals
From $1016 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 $1016 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 $205 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 $205 per night (USD)VRBO
From $292 per night (USD)Expedia
Near Skiing & Hiking: Immaculate Windham Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ample Outdoor Space | 4 Miles to Windham Mountain Resort | Near Colgate Lake Just minutes from Windham, NY, this pristi ...
From $292 per night (USD)Expedia
From $794 per night (USD)VRBO
WINDHAM HOME SLEEPS 10 - 1 MILE TO SLOPES !
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Location, Location, Location - This conveniently located home has you positioned close to all Windham has to offer. 1 mi ...
From $794 per night (USD)VRBO
From $162 per night (USD)Expedia
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 $162 per night (USD)Expedia
From $409 per night (USD)VRBO
Spacious 2-bedroom condo with mountain views & lots of hiking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the best mountain retreat where the beauty of nature is right outside the front door. The only sound you'll h ...
From $409 per night (USD)VRBO
From $338 per night (USD)Expedia
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 $338 per night (USD)Expedia
From $183 per night (USD)VRBO
LUXURY SUITE WITH 2 FULL BEDS
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
HAUS WINDHAM Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility an ...
From $183 per night (USD)VRBO
From $411 per night (USD)Expedia
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 $411 per night (USD)Expedia
From $331 per night (USD)VRBO
Jewett's Gem: a comfortable, cozy, and stylish mountain getaway in the Catskills
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Jewett’s Gem is a cozy two bedroom condo situated between Hunter and Windham Mountains in the heart of the Catskills. F ...
From $331 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 $441 per night (USD)VRBO
Serene Catskills Riverfront Cabin. 3+ Private Acres, HotTub, Deck, Views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Peaceful mountain retreat where nature meets comfort. Set on 3 private acres with a river running through and direct acc ...
From $441 per night (USD)VRBO
From $1839 per night (USD)Expedia
***Your Own Estate***
- Bedrooms:
- 8
- Bathrooms:
- 12
- Sleeps:
- 46
Summary: **Please message us prior to booking and talking with your group to confirm pricing and availability** 12 BR, ...
From $1839 per night (USD)Expedia
From $2418 per night (USD)VRBO
*** Estate Main House***
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 24
Summary: ***PLEASE DO NOT HIT THE “RESERVE” BUTTON UNTIL YOU CONFIRM VIA EMAIL PRICING & AVAILABILITY. USE ONLY THE “CON ...
From $2418 per night (USD)VRBO
From $514 per night (USD)Expedia
Hot Tub • Pool Table • 10 mins to Ski • Cozy Cabin
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Casa Lobo, a newly renovated modern 3-bedroom, 2-bathroom cabin nestled in the heart of the Catskill Mountain ...
From $514 per night (USD)Expedia
From $352 per night (USD)VRBO
Retro Retreat: Charming Home w\/Hot Tub & Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 4
- 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 $352 per night (USD)VRBO
From $491 per night (USD)Expedia
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 $491 per night (USD)Expedia
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 $535 per night (USD)Expedia
4 SEASON VACATION RENTAL
- Bedrooms:
- 3
- 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 $535 per night (USD)Expedia
From $238 per night (USD)VRBO
Ski, Hike,Bike,Golf, Dine within a 6 min Drive. Perfect for a Family getaway
- Bedrooms:
- 2
- 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 $343 per night (USD)Expedia
Cabin Fever Too Cozy & Picturesque Gem with Mountain Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Step into the modern & spacious 2BR 2BA gem nestled in the picturesque and tranquil Catskill Mountains close to scenic h ...
From $343 per night (USD)Expedia
From $339 per night (USD)VRBO
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 $339 per night (USD)VRBO
From $516 per night (USD)Expedia
Catskill Mountain Oasis: sunset terraces, fireplaces, & pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Step into a NEWLY RENOVATED, spacious and modern 4BR, 4BA gem, perfectly positioned in the heart of the Catskills. This ...
From $516 per night (USD)Expedia
From $117 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 $117 per night (USD)VRBO
From $443 per night (USD)Expedia
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)Expedia
From $553 per night (USD)VRBO
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The beautiful stream and open space make this cottage a truly magnificent place. This lovely 1250 square feet two-leve ...
From $553 per night (USD)VRBO
From $666 per night (USD)Expedia
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 $666 per night (USD)Expedia
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 $114 per night (USD)Expedia
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 $114 per night (USD)Expedia
From $126 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 $126 per night (USD)VRBO
From $809 per night (USD)Expedia
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)Expedia
From $513 per night (USD)VRBO
Windham Immaculate Ski Chalet w\/ \nSecluded Fire Pit Available 25\/26 Ski Season!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Available for Season 25/26 Ski Season! $15,000. Nov 15, 2025 - April 15, 2026 This home is a super immaculate, upscale, ...
From $513 per night (USD)VRBO
From $591 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 $591 per night (USD)Expedia
From $669 per night (USD)VRBO
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
- 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 $669 per night (USD)VRBO
From $447 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 $447 per night (USD)Expedia
From $157 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 $157 per night (USD)VRBO
From $172 per night (USD)Expedia
Country Room<br>Inviting, colorful, and cozy room with a Queen Size bed, and en suite bathroom. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Country Room is located on the second floor of Mountain Treasure Bed and Break
- 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)Expedia
From $204 per night (USD)VRBO
Fiddler On The Roof Room<br>Enjoy the mountain view and relax in this bright room, which has a King-Size bed, an en suite bathroom, and mountain views. It sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br> Fiddler On The Roo
- 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 -Pr ...
From $204 per night (USD)VRBO
From $204 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 $204 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. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Art Nouveau Room is located on the second floor of Mountain Treasure
- 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
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Chic Chalet with Hot tub, Fire Pit, mins drive to Windham & Hunter Mountain Ski
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Chalet in Hensonville, NY · ★★★★ ★ · 4 BR · 6 Beds · 2 Baths Welcome to Chic Creek Chalet, a stunning chalet nestled in ...
Click For PricingExpedia
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 $884 per night (USD)Expedia
Tranquil Catskills Hideaway: Contemporary Retreat on 39 Acres
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our stunning contemporary retreat nestled on 39 acres of natural beauty in the enchanting Catskills of New Yo ...
From $884 per night (USD)Expedia
Click For PricingVRBO
4-bedroom chalet just 10 min drive to Hunter Mountain & 5 mins to Windham Ski
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Windham Pine Chalet, a cozy yet elegant chalet nestled in the scenic heart of Catskills. As your host, I'm th ...
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Click For PricingExpedia
Catskill Mountain Ski House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy 2 bedroom condo two minutes from Windham Mountain. Your family will be close to everything when you stay at this ce ...
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Click For PricingVRBO
Spacious 7-bedroom house with AC, WiFi in peaceful Hensonville
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
Get ready to relax in this marvelous 7-bedroom house in Hensonville. With 2 king beds, 3 queen beds, 1 full bed, and 2 t ...
Click For PricingVRBO
From $309 per night (USD)Expedia
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 $309 per night (USD)Expedia
From $196 per night (USD)VRBO
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 $196 per night (USD)VRBO
From $283 per night (USD)Expedia
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 $283 per night (USD)Expedia
From $224 per night (USD)VRBO
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 $224 per night (USD)VRBO
From $422 per night (USD)Expedia
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 $422 per night (USD)Expedia
From $309 per night (USD)VRBO
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 $309 per night (USD)VRBO
From $267 per night (USD)Expedia
LUXURY DUPLEX SUITE WITH JACUZZI
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $267 per night (USD)Expedia
Click For PricingVRBO
Jewett Gem w\/ Charcoal Grill & Mountain Views
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 6
See the hidden beauty of The Empire State when you book your stay at this Jewett vacation rental in the New York country ...
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From $297 per night (USD)Expedia
Windham Pet Friendly home, 2-5min from Ski, Hiking Trials, GoldenLake, Rest&Bars
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our charming house, a beautiful blend of old-world charm and modern comforts. Nestled in the heart of the Mou ...
From $297 per night (USD)Expedia
From $417 per night (USD)VRBO
MTN RETREAT In Windham
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Private 4BR, 2.5 bath contemporary home is situated on a cul-de-sac in Windham, NY The house has an open floor concept, ...
From $417 per night (USD)VRBO
From $970 per night (USD)Expedia
Hilltop Family Escape - 5BR 5BA - Hot Tub & Mountain Views - 4 min. to slopes
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Pack up the family and escape to our Windham timber frame chalet! Take in the stunning views of the mountains, surrounde ...
From $970 per night (USD)Expedia
From $205 per night (USD)VRBO
Cozy Mountain Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Located in the heart of Windham, Land in the Sky, this newly updated condo is your home away from home. For outdoor adve ...
From $205 per night (USD)VRBO
From $380 per night (USD)Expedia
Hot tub, private deck, backyard, near Windham and Hunter ski resorts.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Relax and savor your coffee on the deck while the sun comes up over Hunter, just a few minutes away from skiing at Windh ...
From $380 per night (USD)Expedia
From $459 per night (USD)VRBO
Mountain house w\/ stunning views & gourmet kitchen 7 mi to Windham 9 to Hunter
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Culinary comforts and open-plan living space await you in this sunny mountain refuge. South facing and filled with light ...
From $459 per night (USD)VRBO
From $1482 per night (USD)Expedia
**Your Own Carriage House**
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Summary: ***PLEASE DO NOT HIT THE “RESERVE” BUTTON UNTIL YOU CONFIRM VIA EMAIL PRICING & AVAILABILITY. USE ONLY THE “CON ...
From $1482 per night (USD)Expedia
From $146 per night (USD)VRBO
Black Dome - a 2B, 2B Condo 5 min from Windham, NY, and Windham Mt.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our freshly renovated condo with mountain views is 1000 sf of stylish space. 2 bedrooms upstairs, a fully functioning ki ...
From $146 per night (USD)VRBO
From $436 per night (USD)Expedia
The Garden House - Ski Hunter & Windham
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Garden House is a cedar chalet on a mountaintop in the Great Northern Catskills. It’s a place to slow down, to recha ...
From $436 per night (USD)Expedia