Maplecrest Unit Rentals
- From $1094 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 $1094 per night (USD)VRBO
- Click For Pricing
Expedia
Catskills Cabin Retreat: Hot Tub and Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your new country getaway! Originally built as a seasonal retreat for an acclaimed Vaudeville actress, our ful ...
Click For PricingExpedia
- From $297 per night (USD)
VRBO
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 $297 per night (USD)VRBO
- From $198 per night (USD)
Expedia
Redwood Retreat in Windham - Minutes to Mountain!
- 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 $198 per night (USD)Expedia
- From $286 per night (USD)
VRBO
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 $286 per night (USD)VRBO
- From $630 per night (USD)
Expedia
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 $630 per night (USD)Expedia
- From $162 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 $162 per night (USD)VRBO
- From $422 per night (USD)
Expedia
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 $422 per night (USD)Expedia
- From $417 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 $417 per night (USD)VRBO
- From $292 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 $292 per night (USD)Expedia
- From $325 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 $325 per night (USD)VRBO
- From $247 per night (USD)
Expedia
Cozy Windham Condo - Hot Tub. 5 mins to Windham and 15 to Hunter, close to all.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Perfect 2 bedroom condo. Eat in kitchen with dishwasher, Keurig, toaster, and microwave Cozy living room with Smart TV o ...
From $247 per night (USD)Expedia
- From $196 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 $196 per night (USD)VRBO
- From $3814 per night (USD)
VRBO
*** Estate Main House***
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Summary: ***PLEASE DO NOT HIT THE “RESERVE” BUTTON UNTIL YOU CONFIRM VIA EMAIL PRICING & AVAILABILITY. USE ONLY THE “CON ...
From $3814 per night (USD)VRBO
- From $2823 per night (USD)
VRBO
***Your Own Estate***
- Bedrooms:
- 8
- Bathrooms:
- 12
- Sleeps:
- 34
Summary: **Please message us prior to booking and talking with your group to confirm pricing and availability** 12 BR, ...
From $2823 per night (USD)VRBO
- From $472 per night (USD)
Expedia
Cozy Cabin • Hot Tub • Pool Table • 10 mins to Ski Hunter and Windham
- 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 $472 per night (USD)Expedia
- From $437 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 $437 per night (USD)VRBO
- From $437 per night (USD)
VRBO
Mountain Lodge w\/Hot Tub & Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: All season mountain lodge - skiing, hiking, biking, near Windham & Hunter, NY. Spacious four bedroom getaway in ...
From $437 per night (USD)VRBO
- From $742 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 $742 per night (USD)VRBO
- From $463 per night (USD)
VRBO
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 $463 per night (USD)VRBO
- From $320 per night (USD)
VRBO
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 $320 per night (USD)VRBO
- From $252 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 $252 per night (USD)VRBO
- From $491 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 $491 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 $604 per night (USD)
VRBO
Cozy & Picturesque Gem Mountain View ~ 2 Decks & 2Fireplaces
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Step into the modern & spacious 4BR 4BA gem nestled in a picturesque and tranquil area close to scenic hiking trails, sk ...
From $604 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 $402 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 $402 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 $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 $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 $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 $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 $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 $219 per night (USD)
VRBO
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)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 $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 $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 $819 per night (USD)
VRBO
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 $819 per night (USD)VRBO
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $261 per night (USD)
Expedia
Hot Tub & Fireplace Mountain Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Take the scenic byway up the mountains to your own private getaway! Lounge on either of the two decks, take a relaxing d ...
From $261 per night (USD)Expedia
- From $414 per night (USD)
VRBO
Windham Pet Friendly home, 2-5min from Ski, Hiking Trials, GoldenLake, Rest&Bars
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our charming house, a beautiful blend of old-world charm and modern comforts. Nestled in the heart of the Mou ...
From $414 per night (USD)VRBO
- From $495 per night (USD)
Expedia
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 $495 per night (USD)Expedia
- From $675 per night (USD)
VRBO
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)VRBO
- From $476 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 $476 per night (USD)Expedia
- From $266 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 $266 per night (USD)VRBO
- From $332 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 $332 per night (USD)Expedia
- From $251 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 $251 per night (USD)VRBO
- From $561 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 $561 per night (USD)Expedia
- From $388 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 $388 per night (USD)VRBO
- From $332 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 $332 per night (USD)Expedia
- From $316 per night (USD)
VRBO
Cozy chalet wih hot tub -5 minutes from Windham Mountain
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy Chalet style house nestled in a quiet spot 5 minutes to Windham Mountain and close to hiking trails 15 minutes to H ...
From $316 per night (USD)VRBO
- From $357 per night (USD)
Expedia
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)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $2326 per night (USD)
VRBO
**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 $2326 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- From $402 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 $402 per night (USD)Expedia
- From $284 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 $284 per night (USD)VRBO
- From $410 per night (USD)
Expedia
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 $410 per night (USD)Expedia