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Windham Rentals

From $216 per night (USD)
VRBO
2 Bedroom Townhouse in front of Windham Mountain Ski Resort
Bedrooms:
2
Bathrooms:
2
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 $216 per night (USD)
VRBO
From $1071 per night (USD)
Expedia
Tuscan Year Round Beauty - Pickleball Court - Full Winter Rental Availability
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)
Expedia
From $852 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 $852 per night (USD)
VRBO
From $662 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 $662 per night (USD)
VRBO
From $122 per night (USD)
VRBO
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
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 $122 per night (USD)
VRBO
From $461 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 $461 per night (USD)
VRBO
$Luxury 4BR/4BA Ski-In / Ski-Out Mountain Stay \The Four Ski-sons\$
From $1061 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 $1061 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 $4143 per night (USD)
VRBO
Luxury Mountain Log Home, Ski-In/Ski-Out to Windham Resort
Bedrooms:
7
Bathrooms:
5
Sleeps:
22
* NOTE: Your safety matters. The property features exterior surveillance cameras surrounding the home; these do not look ...
From $4143 per night (USD)
VRBO
From $1304 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 $1304 per night (USD)
VRBO
From $270 per night (USD)
VRBO
5 Minutes from Windham Mountain
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Chalet Chickadee is a beautiful European style 2 bedroom apartment in a duplex chalet style home with Windham Mountain v ...
From $270 per night (USD)
VRBO
From $189 per night (USD)
Expedia
Cutest Cabin in Windham, walking path to pond, corn hole & fire pit, BBQ grill
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Cutest Cabin is the perfect stay for 2 people! Located only minutes away to town & ski slope-snow tubing Across the ...
From $189 per night (USD)
Expedia
From $1926 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 $1926 per night (USD)
VRBO
From $1107 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 $1107 per night (USD)
Expedia
From $548 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 $548 per night (USD)
VRBO
From $605 per night (USD)
Expedia
3 BDRM/2 Bath in Windham Mountain Village Walking Distance To Mountain with view
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Fully furnished 3 Bedroom / 2 Bathroom Condo in Windham Mountain Village, walk to the slopes with amazing mountain views ...
From $605 per night (USD)
Expedia
From $459 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 $459 per night (USD)
VRBO
From $561 per night (USD)
Expedia
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 $561 per night (USD)
Expedia
From $456 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 $456 per night (USD)
VRBO
From $168 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 $168 per night (USD)
Expedia
From $545 per night (USD)
VRBO
Slope Views: Luxe Windham Retreat w/ Hot Tub!
Bedrooms:
3
Bathrooms:
5
Sleeps:
17
Multiple Living Spaces | Outdoor Entertainment Area | Windham Mountain Ski Resort Local wineries, delicious eateries, a ...
From $545 per night (USD)
VRBO
From $1115 per night (USD)
Expedia
5 Bedrooms 5 1/2 Bath Ski Area Views, Walk to Skiing, Huge Common Space & Decks!
Bedrooms:
5
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 $1115 per night (USD)
Expedia
From $482 per night (USD)
VRBO
'The Mountain House:' Windham Retreat w/ Hot Tub!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape the stress of the city with a hiatus to ‘The Mountain House,’ a 4-bedroom, 2-bathroom vacation rental in Windham! ...
From $482 per night (USD)
VRBO
From $3533 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 $3533 per night (USD)
VRBO
Click For Pricing
VRBO
Catskills House: 1 Mi to Windham Mountain Resort!
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
Welcome to the Catskills region, full of scenic mountain views and outdoor adventure! With 6 bedrooms and 2 bathrooms, t ...
Click For Pricing
VRBO
From $351 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 $351 per night (USD)
Expedia
From $1304 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 $1304 per night (USD)
VRBO
From $629 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 $629 per night (USD)
VRBO
$\nStunning Chalet style home in Catskills with 8 Person hot tub, fire pit & Sauna$
From $846 per night (USD)
VRBO
\nStunning Chalet style home in Catskills with 8 Person hot tub, fire pit & Sauna
Bedrooms:
3
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 $846 per night (USD)
VRBO
From $716 per night (USD)
Expedia
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 $716 per night (USD)
Expedia
From $342 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 $342 per night (USD)
VRBO
From $647 per night (USD)
Expedia
Condo in Windham Mountain Village
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Spacious condo for family and friends in WMV, large open space , indoor fireplace , hassle free , steps from the slope, ...
From $647 per night (USD)
Expedia
From $615 per night (USD)
VRBO
Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This is a beautiful log home on 8 acres with amazing views of Windham Mountain. The home is a unique one that is made o ...
From $615 per night (USD)
VRBO
From $377 per night (USD)
VRBO
Windham/Hunter Mountain
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Relax and enjoy our large home located on a private secluded block. Offering 4 master bedrooms with 3 full size bathroo ...
From $377 per night (USD)
VRBO
From $614 per night (USD)
VRBO
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 $614 per night (USD)
VRBO
$\New Home\ Idyllic Mt Views ,Pond & Horse farm views 2 min to Town$
From $504 per night (USD)
Expedia
\"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)
Expedia
From $1591 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 $1591 per night (USD)
VRBO
From $1025 per night (USD)
Expedia
EAT, DRINK, PLAY & RELAX in Windham
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Getaway w/family and friends! From the exciting game room, to the tranquil firepit, to the open floorplan, you, your fa ...
From $1025 per night (USD)
Expedia
From $1589 per night (USD)
VRBO
Windham Private heated indoor pool.
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Escape the big city and visit our newly renovated and furnished Catskill Mountain retreat! Enjoy all the comforts of hom ...
From $1589 per night (USD)
VRBO
From $1101 per night (USD)
Expedia
NEW 5 Bed 5 1/2 Bath Townhouse Walk To Skiing! 900 sq ft Of Mountan View Decks!
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Unit 2: This brand new 3600 square foot townhome boasts 5 bedroom and 5 1/2 baths directly across from Windham Mountain. ...
From $1101 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Gorgeous, First Class, 2 King apartment in downtown Windham
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Gorgeous, brand new, 1000 square foot, 2 king bedroom apartment, located in the heart of downtown Windham..walk to many ...
From $277 per night (USD)
VRBO
From $917 per night (USD)
VRBO
Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Spacious, luxurious, 4500 square foot, 4 bedroom, 3 full bathrooms...hot tub and sauna...20 speaker sound system... hom ...
From $917 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 four bedroom, four bathroom condo right on the slopes at Windham Mountain in New York's Catskill Mountains. T ...
From $802 per night (USD)
VRBO
From $1004 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 $1004 per night (USD)
VRBO
From $292 per night (USD)
VRBO
Red Fox T.H. & Spa hot tub - mini golf tee off & outside living room & firepit
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Red Fox Townhouse is located in Windham! ...
From $292 per night (USD)
VRBO
From $1517 per night (USD)
Expedia
Windham Mountain Village Townhouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Newly Renovated Mountain Side Townhome. Featuring 2 Bedrooms with a Loft. Spacious open concept including a Fire Place, ...
From $1517 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $229 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 $229 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Windham Family Getaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
This three bedroom, two bath home with many new amenities and a wood burning stove sleeps up to 9 people (max 8 adults) ...
From $303 per night (USD)
VRBO
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Expedia
Windham Ridge Townhouse w/ Beautiful Views - Seasonal Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Have your own townhouse and ski at beautiful Windham Mountain. This beautiful townhouse is in great condition with fresh ...
Click For Pricing
Expedia
From $558 per night (USD)
VRBO
Great for Families & Groups!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Newly renovated (4 bed and 2 full baths) Windham Mountain ski house, 3 miles from Windham mountain and 12 miles from Hun ...
From $558 per night (USD)
VRBO
From $229 per night (USD)
Expedia
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
SPACIOUS 2-STORY DOWNTOWN TOWNHOUSE; 12 ft Ceiling and A/C! Relax in the fresh mountain air... 30 foot private balcon ...
From $229 per night (USD)
Expedia
From $1183 per night (USD)
VRBO
ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Welcome to your Windham Retreat! Enjoy incredibly easy access to some of the best skiing in New York. This home has all ...
From $1183 per night (USD)
VRBO
From $2115 per night (USD)
Expedia
NEW 5 Bed 5 1/2 Bath Townhouse Walk To Skiing! 900 sq ft Of Mountan View Decks!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Unit 1: This brand new 3600 square foot townhome boasts 5 bedroom and 5 1/2 baths directly across from Windham Mountain. ...
From $2115 per night (USD)
Expedia
From $185 per night (USD)
VRBO
Cozy Catskill Condo - 2 Mi to Windham Mountain Ski
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A 2-bedroom, 1-bathroom condo sitting only 2.2 miles from the Windham Mountain ski area, this Windham vacation rental ma ...
From $185 per night (USD)
VRBO
From $802 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 $802 per night (USD)
VRBO
From $510 per night (USD)
VRBO
WINDHAM HOME SLEEPS 10 - 1 MILE TO SLOPES !
Bedrooms:
1
Bathrooms:
4
Sleeps:
11
Location, Location, Location - This conveniently located home has you positioned close to all Windham has to offer. 1 mi ...
From $510 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Homey Windham Condo: Hike & Ski the Catskill Mtns!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Get outdoors in the Catskill Mountains with a trip to this 2-bedroom, 1-bathroom Windham vacation rental! Windham Mounta ...
From $245 per night (USD)
Expedia
From $261 per night (USD)
VRBO
Condo w/ Loft: 2 Mi to Windham Mountain Ski!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Get away from the hustle and bustle of city life with a retreat to this 2-bedroom, 1-bath Windham vacation rental! The c ...
From $261 per night (USD)
VRBO
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Expedia
1/2 Mi to Windham Mtn: Main Street Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Walk to Dining | Off-Street Parking | In-Unit Laundry | Gallery Condos Blend small-town charm with all-season fun at t ...
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Expedia
From $203 per night (USD)
VRBO
On the Mountain in Windham, New York in the Catskills
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
4 bedroom, 2 1/2 bath home with renovated kitchen and new baths. Outdoor deck with beautiful views. Master Bedroom wit ...
From $203 per night (USD)
VRBO
From $730 per night (USD)
VRBO
Above & beyond. Perfect house for family, friends & fresh air.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
After a complete renovation we are back and ready to host ! Our condo is perfect for families & friends looking for a gr ...
From $730 per night (USD)
VRBO
From $200 per night (USD)
VRBO
Cozy Caboose in the city
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy, restored 1922 Caboose for rent in the center of downtown Windham...walking distance to restaurants, bars, shops, b ...
From $200 per night (USD)
VRBO
From $463 per night (USD)
Expedia
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 $463 per night (USD)
Expedia
From $1089 per night (USD)
VRBO
ON MTN!Welcome to our Windham MTN Escape! AVAILABLE for 2025 season Dec-Mar
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
I have dates blocked off please send inquiry if you are interested in any dates. PM ME ON FB or send inquiry If interest ...
From $1089 per night (USD)
VRBO
From $854 per night (USD)
VRBO
Stunning Chalet style home with 8 Person Hot Tub, Fire pit & Sauna & steam rm.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
A spectacular open floor plan with a gas fireplace and grand dining room. The entryway has a custom wet bar with wine fr ...
From $854 per night (USD)
VRBO
$Mountain Escape 5 Minutes to Ski Resort\n\n\nGreat Discounted Summer rental !$
From $413 per night (USD)
VRBO
Mountain Escape 5 Minutes to Ski Resort\n\n\nGreat Discounted Summer rental !
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
A 2,700 square foot modern well stocked home with incredible views of Windham mountain. Ski Windham is only 1.5 miles aw ...
From $413 per night (USD)
VRBO
From $217 per night (USD)
Expedia
Peaceful Catskills Condo w/ Deck + Mountain View!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Trade in city crowds for a mountain adventure with this Windham vacation rental as your home base! Perched on a hill ove ...
From $217 per night (USD)
Expedia
From $496 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 $496 per night (USD)
VRBO
From $209 per night (USD)
Expedia
Mountain view apartment, 5mins to Ski Area!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Steps from the Mountain! Just 1 mile away with a crisp mountain view, our beautiful chalet is a mere 5 minute drive from ...
From $209 per night (USD)
Expedia
From $790 per night (USD)
VRBO
Chalet nestled right in Windham Mountain's quiet beauty-private access to trails
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
*WELCOMING INQUIRIES FOR SKI SEASON 2025-26, and SUMMER-FALL GUESTS!!!** Perfect Windham Mountain slope side chalet. ...
From $790 per night (USD)
VRBO
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 $1269 per night (USD)
VRBO
Restored Firehouse One Minute to Skiing on Main St
Bedrooms:
1
Bathrooms:
4
Sleeps:
18
This four bedroom with two baths comes with every amenity. It is located in a restored firehouse with a 16 foot x 9 foo ...
From $1269 per night (USD)
VRBO
From $1100 per night (USD)
VRBO
Summer at Windham Mountain! On mountain 5 bedroom Retreat!
Bedrooms:
3
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 $1100 per night (USD)
VRBO
From $521 per night (USD)
VRBO
Beautifully Restored 6BR in the heart of Windham
Bedrooms:
3
Bathrooms:
6
Sleeps:
13
Enjoy our lovingly restored home in the heart of Windham. Built in 1902, Windham Walk has just finished a complete renov ...
From $521 per night (USD)
VRBO
From $542 per night (USD)
Expedia
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)
Expedia
From $1065 per night (USD)
VRBO
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 $1065 per night (USD)
VRBO
From $318 per night (USD)
VRBO
Windham: Golf, Fish, NY Safety Track, Disc Golf, Hull-O Farms & more all nearby!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Our comfy home has 4 Bedrooms - 2 King size bedrooms, 2 Queen size Bedroom. One full bathroom upstairs and 1 full bat ...
From $318 per night (USD)
VRBO
From $387 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 $387 per night (USD)
VRBO
From $281 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 $281 per night (USD)
Expedia
From $440 per night (USD)
VRBO
Mountain Rental w/ Hot Tub 5 Mins from Windham Mt
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Come relax in our secluded 4 bedroom, 2 bathroom contemporary vacation rental LESS THAN 5 mins from Windham Mt and 15 mi ...
From $440 per night (USD)
VRBO
From $231 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 $231 per night (USD)
Expedia
From $118 per night (USD)
VRBO
Cozy Cabin Condo by the Mountain, 5mins to skiing!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Steps from the Mountain! Just 1 mile away with a crisp mountain view, our beautiful chalet is a mere 5 minute drive from ...
From $118 per night (USD)
VRBO
From $781 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 $781 per night (USD)
Expedia
From $808 per night (USD)
VRBO
Bucolic privacy with Hot Tub in Windham
Bedrooms:
2
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 $808 per night (USD)
VRBO
From $270 per night (USD)
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 ...
From $270 per night (USD)
Expedia
From $2239 per night (USD)
VRBO
*The View* ski in/out modern luxury at Windham Mountain Resort
Bedrooms:
6
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 $2239 per night (USD)
VRBO
Click For Pricing
Expedia
Ski retreat with views of Windham, in heart of town near all.
Bedrooms:
2
Bathrooms:
5
Sleeps:
13
Recently renovated 4-bedroom house with views of the trails on Windham Mountain from 3 of the 4 bedrooms. Ski Windham du ...
Click For Pricing
Expedia
From $750 per night (USD)
VRBO
Panoramic views four minutes to Windham Mountain skiing.
Bedrooms:
2
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 $750 per night (USD)
VRBO
From $710 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 $710 per night (USD)
VRBO
From $390 per night (USD)
VRBO
NEW - Cozy Modern: Stunning views,3 mins ski,BBQ,Fire Pit,Game Room,walk to town
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Windy Hollow! A spacious and newly renovated vacation home with stunning views of Windham Mountain and walkin ...
From $390 per night (USD)
VRBO
From $1956 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 $1956 per night (USD)
VRBO
From $529 per night (USD)
VRBO
Ski house just steps from slopes with indoor pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Come enjoy the Catskills at our spacious Windham Mountain townhome at the base of Windham Mountain. Townhome includes 4B ...
From $529 per night (USD)
VRBO
From $309 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 $309 per night (USD)
Expedia
From $506 per night (USD)
VRBO
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)
VRBO
From $1201 per night (USD)
VRBO
Seasonal Pool Plus Hot Tub & EV Charger 5 mins to Skiing at Windham Mountain
Bedrooms:
4
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 $1201 per night (USD)
VRBO
From $1126 per night (USD)
VRBO
40 acres. seasonal rental.Mountain views.sleeps 12+.perfect for 2 families.
Bedrooms:
3
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 $1126 per night (USD)
VRBO
From $598 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 $598 per night (USD)
Expedia
From $263 per night (USD)
VRBO
PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $263 per night (USD)
VRBO
From $312 per night (USD)
Expedia
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $312 per night (USD)
Expedia

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