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!

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From $118 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 $118 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 $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 $295 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 $295 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 $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, brand new four bedroom, four bathroom condo right on the slopes at Windham Mountain in New York's Catskill Mo ...
From $802 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Close to both Hunter and Windham Mnts
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spacious townhouse has 2 Bedroom, 2 full baths! The first floor had an open floor plan with a fully-stocked kitchen, ...
From $319 per night (USD)
VRBO
$Windham Immaculate Ski Chalet w/ \nSecluded Fire Pit Available 25/26 Ski Season!$
From $506 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 $506 per night (USD)
VRBO
From $131 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 $131 per night (USD)
VRBO
From $809 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 $809 per night (USD)
VRBO
From $115 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 $115 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 $1252 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 $1252 per night (USD)
VRBO
From $609 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 $609 per night (USD)
VRBO
From $693 per night (USD)
VRBO
5-Star Lux Condo, Heated Pool, Hot Tub, Ski in/out @ Windham
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
All of the furniture, linens and amenities are brand new! We are at the base of the mtn and it is ski in/out -- perfec ...
From $693 per night (USD)
VRBO
From $1904 per night (USD)
Expedia
5 Min to Windham Mtn! Luxury Retreat w/ Mountain Views! Natural Swimming Pond
Bedrooms:
7
Bathrooms:
8
Sleeps:
22
Welcome to the Mountain House. Sitting on five beautiful acres with views of 4 of the highest peaks in the Catskills, r ...
From $1904 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 $348 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 $348 per night (USD)
Expedia
From $3780 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 $3780 per night (USD)
VRBO
From $810 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 $810 per night (USD)
VRBO
From $500 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 $500 per night (USD)
VRBO
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 $544 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 $544 per night (USD)
VRBO
From $602 per night (USD)
VRBO
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 $602 per night (USD)
VRBO
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 $1822 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 $1822 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 $173 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 $173 per night (USD)
VRBO
From $1071 per night (USD)
Expedia
Tuscan Year Round Beauty - Pickleball Court
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Among the nicest properties in Windham. Lovely large home nestled quietly on 12 usable acres with bucolic bridle paths j ...
From $1071 per night (USD)
Expedia
From $1760 per night (USD)
VRBO
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 $1760 per night (USD)
VRBO
From $448 per night (USD)
VRBO
SKI Slope views, ski 1 mile drive or walk, Golf Course & walk to town.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cozy one family Colonial/cape style home, with beautiful stone front furnished porch w/BBQ. Full view of Ski Windham Mou ...
From $448 per night (USD)
VRBO
From $693 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 $693 per night (USD)
VRBO
From $341 per night (USD)
VRBO
Hunter/Windham Area - Winter Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Three bedroom ground floor apt close to Hunter Mountain and Windham Mountain in the Catskills in upstate New York.— slee ...
From $341 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 $477 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 $477 per night (USD)
VRBO
$Windham Immaculate Ski Chalet with Awesome Fire Pit.\nAvailable 25/26 Ski Season!$
From $342 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 $342 per night (USD)
VRBO
From $132 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 $132 per night (USD)
Expedia
$Luxury 4BR/4BA Ski-In / Ski-Out Mountain Stay \The Four Ski-sons\$
From $929 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 $929 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 $567 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 $567 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 $716 per night (USD)
Expedia
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)
Expedia
From $160 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 $160 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 $1001 per night (USD)
VRBO
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 $1001 per night (USD)
VRBO
From $658 per night (USD)
VRBO
Vintage Charm Farmhouse Retreat
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Come and enjoy the mountains all year round! This Farmhouse is conveniently located within minutes from Windham and Hunt ...
From $658 per night (USD)
VRBO
From $1544 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 $1544 per night (USD)
VRBO
From $441 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 $441 per night (USD)
Expedia
From $598 per night (USD)
VRBO
Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Tucked away in the forest just a day trip from NYC, you'll find this gem of a mountain retreat where outdoor adventure a ...
From $598 per night (USD)
VRBO
From $290 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 $290 per night (USD)
Expedia
From $605 per night (USD)
VRBO
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)
VRBO
From $232 per night (USD)
Expedia
NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
➤ Nature Immersive Retreat in the Catskills, with Haus Windham Luxury Vacation Rentals! • Serene Getaway near Windham Mo ...
From $232 per night (USD)
Expedia
From $690 per night (USD)
VRBO
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
Bedrooms:
4
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 $690 per night (USD)
VRBO
From $847 per night (USD)
Expedia
NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
➤ Escape to a Nature Immersive Retreat in the Catskills, with Haus Windham Luxury Vacation Rentals! • Serene Getaway nea ...
From $847 per night (USD)
Expedia
From $346 per night (USD)
VRBO
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Escape to this newly renovated mountain cabin just 5 minutes from Windham Mountain ski resort! With a private fishing po ...
From $346 per night (USD)
VRBO
From $1354 per night (USD)
Expedia
Custom Windham Mtn Villa w/ Pool, Theater & Views!
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
The poster child for a 'dream house,' this stunning 5-bedroom, 4.5-bath vacation rental is sure to be adored by luxury t ...
From $1354 per night (USD)
Expedia
From $1172 per night (USD)
VRBO
Lux Windham Getaway | Views & Indoor Heated Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Summary: Welcome to your luxury mountain retreat — the perfect blend of high-end comfort and alpine charm. Perched to ca ...
From $1172 per night (USD)
VRBO
From $804 per night (USD)
Expedia
Mountain Escape: 5BR Chalet | 6 Min to Ski Resort
Bedrooms:
4
Bathrooms:
6
Sleeps:
15
Experience the allure of this 3300 sq ft chalet boasting 5 bedrooms and 4 baths, ideally situated directly across from W ...
From $804 per night (USD)
Expedia
From $3184 per night (USD)
VRBO
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
This Windham cabin minutes from Hunter and Windham Mountains, boasts 6 inviting bedrooms, including 1 king bed, 4 queen ...
From $3184 per night (USD)
VRBO
From $255 per night (USD)
Expedia
2 Mi to Windham Mountain: Scenic Home w/ Fire Pit!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Updated Interior w/ Modern Decor & Appliances | Office w/ Dedicated Workspace & Large Windows | Pet Friendly w/ Fee Qui ...
From $255 per night (USD)
Expedia
From $387 per night (USD)
VRBO
Beautiful Windham Chalet 2 minutes to Town and the Mountain
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Beautiful Chalet with a host of year-round activities! Close to skiing, snowboarding, sledding, snowshoeing, mountain bi ...
From $387 per night (USD)
VRBO
From $2769 per night (USD)
VRBO
6-bedroom SKI Off Chateau at Windham Mountain Club with WiFi
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Escape to this superb 6-bedroom Ski Off Chateau at Windham Mountain Club and enjoy Apres-Ski Each room of this Smart ho ...
From $2769 per night (USD)
VRBO
From $608 per night (USD)
VRBO
Spacious 5-bedroom house in marvelous Windham with AC, WiFi & wood burning stove
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Experience the Catskills at The Quad Six, a spacious 5-bedroom, 2-bathroom vacation home in Windham, NY. Located near bo ...
From $608 per night (USD)
VRBO
$Mtn-View Home w\/ Deck on 4 Acres in Windham$
From $281 per night (USD)
Expedia
Mtn-View Home w\/ Deck on 4 Acres in Windham
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
5 Mi to Windham Mountain Club | Remote Workers Welcome Tucked away in the heart of Windham, this 3-bedroom, 2-bath vac ...
From $281 per night (USD)
Expedia
Click For Pricing
VRBO
Fully updated townhome 200 feet from slopes of Windham Mountain
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This 3-bedroom 3 bath townhome 200 feet from the Windham ski lift is perfect for your escape. With a king bed, 2 bunk be ...
Click For Pricing
VRBO
From $1295 per night (USD)
Expedia
5-Bedroom Luxury Home on 7 Secluded Acres (10min from Windham Mountain)
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Enjoy a day on the slopes or hiking, followed by a hot tub for sore muscles, wine by the fire, or a movie in the games r ...
From $1295 per night (USD)
Expedia
From $1377 per night (USD)
VRBO
Reduced May Rates - Plus Special Culinary Promotion! Details Below!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Reduced May Rates - Plus Special Culinary Promotion! Details Below! Breathtaking Design, Newly Constructed Farmhouse wit ...
From $1377 per night (USD)
VRBO
From $1377 per night (USD)
Expedia
Reduced May Rates - Plus Special Culinary Promotion! Details Below!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Reduced May Rates - Plus Special Culinary Promotion! Details Below! Breathtaking Design, Newly Constructed Farmhouse wit ...
From $1377 per night (USD)
Expedia
From $5054 per night (USD)
VRBO
Spacious 5-bedroom house in charming Windham centrally located in town.
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Windham is waiting for you at this 5-bedroom house. This beautiful property features 4 queen beds and 1 king bed, perfec ...
From $5054 per night (USD)
VRBO
From $540 per night (USD)
Expedia
Mountain Chalet with Hot Tub, Ski, & Amazing Views!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
*New Listing Discount applied to all bookings made before 5/30/25!!* Chalet retreat in Hensonville, nestled convenientl ...
From $540 per night (USD)
Expedia
From $261 per night (USD)
VRBO
Ski, Hike & Golf: Pet-Friendly Windham Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
2 Mi to Windham Mountain Club | Furnished Deck | Peaceful, Wooded Surroundings | Fireplace Surrounded by lush woodlands ...
From $261 per night (USD)
VRBO
From $172 per night (USD)
Expedia
Country Room. Cozy room with a Queen-Size bed, en-suite bathroom, and FREE breakfast. Sleeps 2.
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 $192 per night (USD)
VRBO
Fiddler On The Roof Room<br>Room with mountain views, a King-Size bed, en suite bathroom, and FREE breakfast. It sleeps 2.
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 $192 per night (USD)
VRBO
From $205 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 $205 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.FREE breakfast. Sleeps 2.
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
From $448 per night (USD)
Expedia
3-bedroom All-Season condo at Enclave in amazing Windham ON MOUNTAIN
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Discover this marvelous 3-bedroom gem in Windham. This delightful condo features 2 king beds and 2 sets of bunk beds, pe ...
From $448 per night (USD)
Expedia
From $1307 per night (USD)
VRBO
Entire lodge in Windham, New York on 12 acres and bordering a state park
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Discover the charm of Windham, NY, a four-season retreat in the Catskill Mountains, just two hours from NYC! Mt. Pisgah ...
From $1307 per night (USD)
VRBO
From $1005 per night (USD)
Expedia
Brand NEW MINT Windham 5BR/4.5BA home on 5 acre, wooded hilltop.
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
MINT 5BR, 4.5BA, brand new home. Full modern furnishing complete 5/1. Panoramic views from 5 acre hilltop with forest ba ...
From $1005 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Ski, Hike & More: Year-Round Gem in Windham
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Walk to Main Street Shops & Restaurants | Amazing Bird Watching | Secluded Deck w/ Grill Escape to the mountains at thi ...
From $296 per night (USD)
VRBO
From $427 per night (USD)
Expedia
MIRROR CABIN IN THE FOREST WITH HOT TUB
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Haus Windham - 2 hours from NYC! ➤ Escape to our serene mirror Glass-Walled cabin nestled in the forested mou ...
From $427 per night (USD)
Expedia
From $810 per night (USD)
VRBO
Woodside Cabin #2 on Lake Heloise
Bedrooms:
1
Bathrooms:
1
Sleeps:
18
Charming cabin to stay and play in at the lake. Have fun swimming and fishing on the lake. This property was a campsite ...
From $810 per night (USD)
VRBO
From $405 per night (USD)
VRBO
Sauna, Mnt Views, Hot tub, <2 mins to slopes
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You'll love our Ski house for your trip to Windham Mountain! Here's why: - Centrally located to 2 mins from the village ...
From $405 per night (USD)
VRBO
From $1449 per night (USD)
VRBO
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. 5 min from Windham Ski
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Black Bear Cabin: Your Luxurious Mountain Retreat Luxury 3,300 sqft Ski and Golf Chalet with 4 bedrooms + 4 ensuite bat ...
From $1449 per night (USD)
VRBO
From $1278 per night (USD)
VRBO
Ski-in, Ski-out GORGEOUS mountain chalet in prime location
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Beautiful wood and stone chalet directly off a green level ski/summer bike or hike run close to base of Windham mountain ...
From $1278 per night (USD)
VRBO
$LUXURIOUS & SERENE SKI-IN/ SKI-OUT \Winterfell\ LODGE$
From $1818 per night (USD)
VRBO
LUXURIOUS & SERENE SKI-IN/ SKI-OUT \"Winterfell\" LODGE
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Welcome to an unparalleled luxury living experience at this exquisite post-and-beam, charming **Ski-in/ Ski-Out, lodge o ...
From $1818 per night (USD)
VRBO
From $243 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 $243 per night (USD)
Expedia
From $589 per night (USD)
VRBO
Beautiful Catskills country retreat --neighboring reservoir/recreation area
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
The dancing bear welcomes you to our beautiful, fully restored, 1800’s farmhouse on 5 acres of woods and a large grass y ...
From $589 per night (USD)
VRBO
From $259 per night (USD)
Expedia
Big Hollow Board and Batten House with Nerf Treehouse!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Come enjoy the Catskills! Nestled directly between Windham and Hunter Ski Mountains. Hiking trails a mile down the dead- ...
From $259 per night (USD)
Expedia
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 $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 $432 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 $432 per night (USD)
VRBO
From $2184 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 $2184 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 $593 per night (USD)
VRBO
Spacious Mountain Escape - Minutes to Windham/Hunter
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Spacious, light-infused contemporary on park-like grounds just minutes from Windham and Hunter ski areas. Multiple wood ...
From $593 per night (USD)
VRBO
From $787 per night (USD)
VRBO
Ski Ridge Golf farmhouse
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Relax in this beautiful natural setting course that Windham has to offer, while at the same time enjoying all comforts o ...
From $787 per night (USD)
VRBO
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

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