Town of Windham, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Windham, New York on RentalSaver.com!

Town of Windham Rentals

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 $196 per night (USD)
Expedia
Cutest Cabin in Windham walking trail to MTN views corn hole mini golf 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 $196 per night (USD)
Expedia
From $610 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 $610 per night (USD)
VRBO
From $665 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 $665 per night (USD)
Expedia
From $679 per night (USD)
VRBO
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 $679 per night (USD)
VRBO
From $1625 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 $1625 per night (USD)
VRBO
From $1226 per night (USD)
VRBO
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 $1226 per night (USD)
VRBO
From $1052 per night (USD)
Expedia
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 $1052 per night (USD)
Expedia
From $606 per night (USD)
VRBO
Luxurious Mt Retreat Sauna Hot Tub Fire Pit & Park
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Indulge in this picturesque setting of our 4BR 2BA log home on a spacious, park-like property just a short drive away fr ...
From $606 per night (USD)
VRBO
From $305 per night (USD)
Expedia
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 $305 per night (USD)
Expedia
From $1517 per night (USD)
VRBO
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)
VRBO
From $231 per night (USD)
VRBO
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 $231 per night (USD)
VRBO
From $247 per night (USD)
VRBO
Cozy Gateway Gem for 2 at Widham
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A beautifully renovated condo at the Quads. Almost 600 sq of living space to your disposal with a separate bedroom and ...
From $247 per night (USD)
VRBO
Click For Pricing
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 $303 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 $303 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Redwood Retreat in Windham - minutes to Mtn!
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 $202 per night (USD)
Expedia
From $662 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 $662 per night (USD)
VRBO
From $198 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 $198 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 $497 per night (USD)
VRBO
Pet-Friendly New York Cabin w/ Hot Tub & Game Room
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
- 2,200 Sq Ft - Hiking Nearby Privacy and spectacular views make this cabin a must-stay! The 4-bed, 3-bath vacation re ...
From $497 per night (USD)
VRBO
From $510 per night (USD)
Expedia
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)
Expedia
From $181 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 $181 per night (USD)
VRBO
From $1089 per night (USD)
Expedia
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)
Expedia
From $518 per night (USD)
VRBO
Windham Mountain Chalet with Treehouse sleeps 15, Game Room & fireplace
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
Large Four season country vacation house in the heart of the Windham wirh a beautiful trehouse. Close enough to all the ...
From $518 per night (USD)
VRBO
From $1828 per night (USD)
Expedia
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 $1828 per night (USD)
Expedia
From $755 per night (USD)
VRBO
Catskills Windham Hunter Mountain Cabin Getaway
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Here is your ski weekend! This is Your cozy cabin getaway near Windham and Hunter! You can rejuvenate your senses surrou ...
From $755 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 $1451 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 $1451 per night (USD)
VRBO
From $286 per night (USD)
Expedia
4 bedroom house 10 minutes to Windham Mountain
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Quiet 4 bedroom house with a nice sized living room with an indoor fireplace, a sunroom with beautiful views, a dining r ...
From $286 per night (USD)
Expedia
From $1058 per night (USD)
VRBO
Windham Farmhouse Escape w/hot tub
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Set on 8+ acres, this former dairy farm is a breath of fresh air. The farmhouse, built in 1838, maintains its original c ...
From $1058 per night (USD)
VRBO
From $397 per night (USD)
Expedia
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 $397 per night (USD)
Expedia
From $315 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 $315 per night (USD)
VRBO
From $164 per night (USD)
Expedia
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 $164 per night (USD)
Expedia
From $290 per night (USD)
VRBO
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 $290 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Ski on and Off Windham Mountain Village Townhome Unit
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This is a townhouse unit located within the Windham Mountain Village Association. It is located at at the base of Windh ...
From $270 per night (USD)
Expedia
From $392 per night (USD)
VRBO
The Ultimate Windham Getaway With Hot Tub & Sauna
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Ready for the season, this retreat is perfectly situated in the town of Windham, New York. Whether it’s hike, bike, or s ...
From $392 per night (USD)
VRBO
From $1063 per night (USD)
Expedia
Après Chalet|Ski|Luxury|Sauna|HotTub|Firepit|Disco
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
About this space Nestled in the heart of the Catskills, this Windham retreat offers both adventure and serenity, just 5 ...
From $1063 per night (USD)
Expedia
From $254 per night (USD)
VRBO
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 $254 per night (USD)
VRBO
From $1293 per night (USD)
Expedia
Contemporary Renovated Retreat with Mountain Views, Ski-In/Ski-Out,...
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Windham Mountainside Marvel Contemporary Renovated Retreat with Mountain Views, Ski-In/Ski-Out, Spacious Living Spaces ...
From $1293 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Whispering River - Catskills New York
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to the newly renovated house with central Heating and Cooling located just minutes from skiing, hiking and every ...
From $255 per night (USD)
VRBO
From $691 per night (USD)
VRBO
THE PAINTED COW- 5 acre farm, walk to Mainstreet, 1 mile to slopes in Windham!!
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Highest-rated superhost Airbnb- new to VRBO! Escape to Nature in All Four Seasons at this beautifully renovated 1900s f ...
From $691 per night (USD)
VRBO
From $349 per night (USD)
VRBO
Charming 3-bedroom farmhouse with hot tub in the Catskills
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this serene 3-bedroom, 2-bathroom home nestled in the heart of Windham, NY! Perfect for a relaxing family geta ...
From $349 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Located in Windham, enjoy what this 3-bedroom house has to offer. With 2 king beds and 1 full bed, guests can relax in t ...
From $301 per night (USD)
Expedia
From $358 per night (USD)
VRBO
Fabulous house with AC in charming Windham-located right by Windham Mountain
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located in Windham, this house is a dream. With 4 bathrooms equipped with amenities like a bathtub and hair dryer, guest ...
From $358 per night (USD)
VRBO
From $587 per night (USD)
VRBO
Amazing Location, Steps Away from Magic Carpet to Main Lodge.
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Welcome to a “Change of Altitude,” an immaculate 3 Bedroom/3 Bath Townhouse that’s a short walk from Windham Main Lodge ...
From $587 per night (USD)
VRBO
From $247 per night (USD)
VRBO
Ski, Hike,Bike,Golf, Dine within a 6 min Drive. Perfect for a Family getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Gorgeous, newly renovated, corner unit with L shaped deck,2 bedroom, 2 bath with picturesque views featuring main level ...
From $247 per night (USD)
VRBO
From $400 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 $400 per night (USD)
VRBO
From $547 per night (USD)
VRBO
4 SEASON VACATION RENTAL
Bedrooms:
2
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 $547 per night (USD)
VRBO
From $387 per night (USD)
Expedia
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)
Expedia
From $569 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 $569 per night (USD)
VRBO
From $495 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 $495 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 $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 $351 per night (USD)
VRBO
*GUT RENO 4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*Windhm Mtn View*2BBQs
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Featured in New York Magazine and Awarded as a Top Choice Getaway in Windham, NY the Gem of the Catkills, Upstate New Yo ...
From $351 per night (USD)
VRBO
From $555 per night (USD)
Expedia
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 $555 per night (USD)
Expedia
From $783 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 $783 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
From $679 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 $679 per night (USD)
VRBO
From $540 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 $540 per night (USD)
Expedia
From $1000 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 $1000 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 $856 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 $856 per night (USD)
VRBO
From $306 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 $306 per night (USD)
VRBO
From $443 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 $443 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
$Windham Immaculate Ski Chalet w/ \nSecluded Fire Pit Available 25/26 Ski Season!$
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 $153 per night (USD)
VRBO
Catskill Domeo - Romantic Magical Geodesic Glamping Dome in Catskill Mountains
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Catskill Domeo. You will love it so much, it will feel like it is forbidden! ;) Beautiful birch work throughout the ent ...
From $153 per night (USD)
VRBO
From $680 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 $680 per night (USD)
VRBO
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 $127 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 $127 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 $918 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 $918 per night (USD)
VRBO
From $522 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 $522 per night (USD)
VRBO
From $419 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 $419 per night (USD)
VRBO
From $738 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 $738 per night (USD)
Expedia
From $477 per night (USD)
VRBO
Newly Renovated House ~ Secluded 5 Acre Retreat ~ Peaceful and Quiet
Bedrooms:
2
Bathrooms:
3
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 $477 per night (USD)
VRBO
From $463 per night (USD)
VRBO
Private family home! 4 miles to Windham Mtn!
Bedrooms:
3
Bathrooms:
3
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 $463 per night (USD)
VRBO
From $1404 per night (USD)
VRBO
EXCLUSIVE, EXQUISITE & UNFORGETTABLE MOUNTAIN OASIS
Bedrooms:
7
Bathrooms:
9
Sleeps:
18
Copper Ridge Estate | 9BR Luxury Mountain Retreat w/ Theater, Pool, Gym & Concierge Sleeps 18 · 9 Bedrooms · 8+ Baths · ...
From $1404 per night (USD)
VRBO
From $819 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 $819 per night (USD)
VRBO
From $447 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 $447 per night (USD)
VRBO
$4BR TOWNHOUSE MINUTES TO WINDHAM & HUNTER\nFree shuttle to Windham Mnt ski season$
From $211 per night (USD)
VRBO
4BR TOWNHOUSE MINUTES TO WINDHAM & HUNTER\nFree shuttle to Windham Mnt ski season
Bedrooms:
3
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 $211 per night (USD)
VRBO
From $1953 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 $1953 per night (USD)
VRBO
From $589 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 $589 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 $550 per night (USD)
Expedia
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 $550 per night (USD)
Expedia
From $1346 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 $1346 per night (USD)
VRBO
From $284 per night (USD)
Expedia
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 $284 per night (USD)
Expedia
From $1071 per night (USD)
VRBO
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
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)
VRBO
From $1879 per night (USD)
Expedia
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
Bedrooms:
5
Bathrooms:
9
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 $1879 per night (USD)
Expedia
From $783 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 $783 per night (USD)
VRBO
From $529 per night (USD)
VRBO
Near Hunter and Windham ski resorts. Crystal Pond town house, 4BR & 3.5 bath
Bedrooms:
3
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 $529 per night (USD)
VRBO
$Windham Immaculate Ski Chalet with Awesome Fire Pit.\nAvailable 25/26 Ski Season!$
From $337 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 $337 per night (USD)
VRBO
From $140 per night (USD)
Expedia
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 $140 per night (USD)
Expedia
From $716 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 $716 per night (USD)
VRBO
From $605 per night (USD)
Expedia
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 $605 per night (USD)
Expedia
From $1739 per night (USD)
VRBO
7 Bedroom Luxurious Chalet In Windham, NY
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
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 $1739 per night (USD)
VRBO
From $459 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 $459 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
From $1010 per night (USD)
Expedia
Amazing Mountain View’s from every room! Hot Tub/3 Fire pits & Game Rm
Bedrooms:
3
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 $1010 per night (USD)
Expedia

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Results: 194 Rentals