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

Filter

Popular Areas

$All Season Luxury Condo in Windham\/ Ski On - Ski Off$
From $1200 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 $1200 per night (USD)
VRBO
From $317 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 $317 per night (USD)
VRBO
From $463 per night (USD)
VRBO
Retreat mountain home
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Fully furnished, very comfortable, open living space. Property situated on 10+ beautiful acres in the Catskill mountains ...
From $463 per night (USD)
VRBO
From $926 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 $926 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 $662 per night (USD)
VRBO
Year-Round Relaxing Mountain Escape
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Luxury 6 Bedroom year-round retreat nestled in secluded pine forest. Large open floor plan with vaulted ceilings great f ...
From $662 per night (USD)
VRBO
$Relax!! Escape the city!! Updated condo w Mtn views from deck w\/ turbo internet$
From $208 per night (USD)
VRBO
Relax!! Escape the city!! Updated condo w Mtn views from deck w\/ turbo internet
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Chic, spacious updated two level corner unit townhouse. Freshly painted a serene light gray, brand new barn wood floorin ...
From $208 per night (USD)
VRBO
$with Secluded Fire Pit\nUltra Clean, Modern, Close to Windham Mountain.$
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 $712 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 $712 per night (USD)
VRBO
$Cozy Windham\/Hunter Getaway$
From $174 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 $174 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
$Modern Mountain House 5Bd\/3Ba, HotTub, 4 Season Room, 5 min from Windham Mtn$
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 $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
$\New Home\ Idyllic Mt Views ,Pond & Horse farm views 2 min to Town$
From $575 per night (USD)
VRBO
\"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 $575 per night (USD)
VRBO
From $1236 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 $1236 per night (USD)
VRBO
$5-Star Lux Condo, Heated Pool, Hot Tub, Ski in\/out @ Windham$
From $909 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 $909 per night (USD)
VRBO
$5 Min to Windham Mtn! Luxury Retreat w\/ Mountain Views! Natural Swimming Pond$
From $2410 per night (USD)
VRBO
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 $2410 per night (USD)
VRBO
From $429 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 $429 per night (USD)
VRBO
From $3571 per night (USD)
VRBO
EXCLUSIVE, EXQUISITE & UNFORGETTABLE MOUNTAIN OASIS
Bedrooms:
8
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 $3571 per night (USD)
VRBO
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
$Catskill MTN House w\/ Hot Tub and Large Outdoor Decks, fire-pit, close to hiking$
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 $408 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 $408 per night (USD)
VRBO
From $441 per night (USD)
Expedia
Newly Renovated House ~ Secluded 5 Acre Retreat ~ Peaceful and Quiet
Bedrooms:
3
Bathrooms:
4
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 $441 per night (USD)
Expedia
From $429 per night (USD)
VRBO
Private family home! 4 miles to Windham Mtn!
Bedrooms:
3
Bathrooms:
4
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 $429 per night (USD)
VRBO
From $490 per night (USD)
Expedia
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 $490 per night (USD)
Expedia
From $634 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 $634 per night (USD)
VRBO
$Windham Mountain Village - Walk to Slopes - 2 Bedroom\/2 Bathroom Condo$
From $471 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 $471 per night (USD)
VRBO
From $1800 per night (USD)
VRBO
Windham Log Cabin on 35 Acres. Family friendly.
Bedrooms:
5
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 $1800 per night (USD)
VRBO
$4BR TOWNHOUSE MINUTES TO WINDHAM & HUNTER\nFree shuttle to Windham Mnt ski season$
From $482 per night (USD)
VRBO
4BR TOWNHOUSE MINUTES TO WINDHAM & HUNTER\nFree shuttle to Windham Mnt ski season
Bedrooms:
4
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 $482 per night (USD)
VRBO
From $1162 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 $1162 per night (USD)
VRBO
From $538 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 $538 per night (USD)
VRBO
$5-Star. Luxury Condo, Heated Pool, Hot Tub, Ski in\/out @ Windham$
From $745 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 $745 per night (USD)
VRBO
$Hunter\/Windham Area - Winter Rental$
From $355 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 $355 per night (USD)
VRBO
From $625 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 $625 per night (USD)
VRBO
From $508 per night (USD)
VRBO
Near Hunter and Windham ski resorts. Crystal Pond town house, 4BR & 3.5 bath
Bedrooms:
4
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 $508 per night (USD)
VRBO
From $992 per night (USD)
VRBO
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 $992 per night (USD)
VRBO
From $1206 per night (USD)
Expedia
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
Bedrooms:
5
Bathrooms:
10
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 $1206 per night (USD)
Expedia
From $235 per night (USD)
VRBO
2 Bedroom Townhouse in front of Windham Mountain Ski Resort
Bedrooms:
2
Bathrooms:
3
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 $235 per night (USD)
VRBO
$Windham Immaculate Ski Chalet with Awesome Fire Pit.\n\n\n$
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 $140 per night (USD)
VRBO
Studio 3 BEDS-SLEEPS 3
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)
VRBO
From $379 per night (USD)
VRBO
Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Alpine Escape! Enjoy incredibly easy access to some of the best skiing in New York. This home has all the e ...
From $379 per night (USD)
VRBO
$Luxury 4BR\/4BA Ski-In \/ Ski-Out Mountain Stay \The Four Ski-sons\$
From $1373 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 $1373 per night (USD)
VRBO
From $355 per night (USD)
VRBO
Windham Mountain Ski House with great views of Windham and the Valley.
Bedrooms:
2
Bathrooms:
5
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 $355 per night (USD)
VRBO
$Luxury Mountain Log Home, Ski-In\/Ski-Out to Windham Resort$
From $4367 per night (USD)
VRBO
Luxury Mountain Log Home, Ski-In\/Ski-Out to Windham Resort
Bedrooms:
8
Bathrooms:
6
Sleeps:
22
* NOTE: Your safety matters. The property features exterior surveillance cameras surrounding the home; these do not look ...
From $4367 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 $638 per night (USD)
VRBO
Panoramic views four minutes to Windham Mountain skiing.
Bedrooms:
3
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 $638 per night (USD)
VRBO
From $219 per night (USD)
Expedia
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)
Expedia
$Amazing Mountain View’s from every room! Hot Tub\/3 Fire pits & Game Rm$
From $980 per night (USD)
VRBO
Amazing Mountain View’s from every room! Hot Tub\/3 Fire pits & Game Rm
Bedrooms:
4
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 $980 per night (USD)
VRBO
From $703 per night (USD)
Expedia
Vintage Charm Farmhouse Retreat
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Come and enjoy the mountains all year round! This Farmhouse is conveniently located within minutes from Windham and Hunt ...
From $703 per night (USD)
Expedia
From $1588 per night (USD)
VRBO
7 Bedroom Luxurious Chalet In Windham, NY
Bedrooms:
4
Bathrooms:
7
Sleeps:
16
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 $1588 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 $560 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 $560 per night (USD)
VRBO
From $273 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 $273 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces
Bedrooms:
4
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 $515 per night (USD)
VRBO
From $392 per night (USD)
Expedia
NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $392 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
$NEW OUTDOOR HOT TUB!! 5 BEDROOM\/3 BATH CHALET - HAUS WINDHAM$
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 $540 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 $540 per night (USD)
VRBO
From $719 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 $719 per night (USD)
Expedia
From $634 per night (USD)
VRBO
Windham Luxury Pet Friendly Retreat.
Bedrooms:
3
Bathrooms:
3
Sleeps:
11
New log-style home fully furnished on 3 levels; family rooms on the 1st and 2nd levels; lower level radiant heated tile ...
From $634 per night (USD)
VRBO
From $3387 per night (USD)
Expedia
Spacious 6-bedroom cabin in cool Windham with AC, WiFi
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
This Windham cabin boasts 6 inviting bedrooms, including 1 king bed, 4 queen beds, and 3 bunk beds. With amenities like ...
From $3387 per night (USD)
Expedia
$2 Mi to Windham Mountain: Scenic Home w\/ Fire Pit!$
From $258 per night (USD)
VRBO
2 Mi to Windham Mountain: Scenic Home w\/ Fire Pit!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Updated Interior w/ Modern Decor & Appliances | Office w/ Dedicated Workspace & Large Windows | Pet Friendly w/ Fee Qui ...
From $258 per night (USD)
VRBO
$Welcome to our home in the mountains, 2 hrs from NYC. 6BR, sleeps 12. Ski in\/out$
From $1107 per night (USD)
Expedia
Welcome to our home in the mountains, 2 hrs from NYC. 6BR, sleeps 12. Ski in\/out
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Welcome to our home in the mountains, 2 hrs from NYC. 6BR, 5.5 bathrooms. sleeps 12 people - hot tub and some great vie ...
From $1107 per night (USD)
Expedia
$Custom Windham Mtn Villa w\/ Pool, Theater & Views!$
From $1465 per night (USD)
VRBO
Custom Windham Mtn Villa w\/ Pool, Theater & Views!
Bedrooms:
5
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 $1465 per night (USD)
VRBO
From $961 per night (USD)
Expedia
NEW Modern Cabin | 8 Mins From Skiing | Hot Tub
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Sophie’s Summit Lodge is located in the heart of the Catskills in historic Windham, NY. Our 5 BD and 5 BA cabin features ...
From $961 per night (USD)
Expedia
From $1574 per night (USD)
VRBO
Modern Ski-View Pool House: Contemporary Comfort in Windham, New York
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
Welcome to our inviting ski-view getaway in Windham, New York! Perched on the slopes, this vrbo promises a ski enthusias ...
From $1574 per night (USD)
VRBO
From $1438 per night (USD)
VRBO
Luxurious Penthouse with Full Mountain Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
High-end ski-in/ski-out condo located steps away from Whisper Run on Windham Mountain fully-appointed with top notch fur ...
From $1438 per night (USD)
VRBO
$Windham Mountain ski on\/off 3br condo. Pool, Common areas, boot room and gym!$
From $1312 per night (USD)
VRBO
Windham Mountain ski on\/off 3br condo. Pool, Common areas, boot room and gym!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Discover this meticulously maintained true ski on/off 3 BR 3 full bath gem at Windham Mountain Club. Located in the cove ...
From $1312 per night (USD)
VRBO
$Mtn-View Home w\/ Deck on 4 Acres in Windham$
From $228 per night (USD)
Expedia
Mtn-View Home w\/ Deck on 4 Acres in Windham
Bedrooms:
2
Bathrooms:
3
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 $228 per night (USD)
Expedia
From $1129 per night (USD)
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 ...
From $1129 per night (USD)
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 $792 per night (USD)
VRBO
Breathtaking Design, Newly Constructed Farmhouse with Wooded Views in Windham NY
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Brand-new construction! Modern farmhouse offers the perfect blend of beauty & peace of the mountains, and the luxurious ...
From $792 per night (USD)
VRBO
From $400 per night (USD)
Expedia
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 $400 per night (USD)
Expedia
From $2550 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 $2550 per night (USD)
VRBO
From $598 per night (USD)
Expedia
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 $598 per night (USD)
Expedia
$LUXURIOUS & SERENE SKI-IN\/ SKI-OUT \Winterfell\ LODGE$
From $1860 per night (USD)
VRBO
LUXURIOUS & SERENE SKI-IN\/ SKI-OUT \"Winterfell\" LODGE
Bedrooms:
7
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 $1860 per night (USD)
VRBO
From $1271 per night (USD)
VRBO
Ski-in, Ski-out GORGEOUS mountain chalet in prime location
Bedrooms:
4
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 $1271 per night (USD)
VRBO
$Beautiful Catskills country retreat --neighboring reservoir\/recreation area$
From $546 per night (USD)
VRBO
Beautiful Catskills country retreat --neighboring reservoir\/recreation area
Bedrooms:
3
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 $546 per night (USD)
VRBO
From $656 per night (USD)
Expedia
~ Alpine 5BR Chalet: 6 min to SKI | Sleeps 20 ~
Bedrooms:
4
Bathrooms:
5
Sleeps:
20
Experience the allure of this 3300 sq ft chalet boasting 5 bedrooms and 4 baths, ideally situated directly across from W ...
From $656 per night (USD)
Expedia
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 $490 per night (USD)
VRBO
Ski house just steps from slopes with indoor pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Come enjoy the fall and winter at this great Windham Mountain townhome at the base of Windham Mountain. Space includes 4 ...
From $490 per night (USD)
VRBO
From $240 per night (USD)
VRBO
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 $240 per night (USD)
VRBO
$Spacious Mountain Escape - Minutes to Windham\/Hunter$
From $646 per night (USD)
VRBO
Spacious Mountain Escape - Minutes to Windham\/Hunter
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Spacious, light-infused contemporary on park-like grounds just minutes from Windham and Hunter ski areas. Multiple wood ...
From $646 per night (USD)
VRBO
From $1811 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 $1811 per night (USD)
VRBO
$*The View* ski in\/out modern luxury at Windham Mountain Resort$
From $2019 per night (USD)
VRBO
*The View* ski in\/out modern luxury at Windham Mountain Resort
Bedrooms:
7
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 $2019 per night (USD)
VRBO
$Escape to the mountains on 5 acres, 5 minutes to Windham Resort w\/ all Amenities$
From $463 per night (USD)
VRBO
Escape to the mountains on 5 acres, 5 minutes to Windham Resort w\/ all Amenities
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Just a 2.5-hour drive from NYC, you can escape to a relaxing, newly built and furnished modern cabin on five acres of wo ...
From $463 per night (USD)
VRBO
$2 Bed Ski-In\/Out Condo$
From $657 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 $657 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
$Rare Ski-In\/Ski-Out Townhome! Windham Mountain at your back door!$
From $1836 per night (USD)
VRBO
Rare Ski-In\/Ski-Out Townhome! Windham Mountain at your back door!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
The rare opportunity to rent an Enclave Townhome is here! Stay in one of the most sought-after locations at the base of ...
From $1836 per night (USD)
VRBO
From $839 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 $839 per night (USD)
Expedia
From $749 per night (USD)
VRBO
Bucolic privacy with Hot Tub in Windham
Bedrooms:
3
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 $749 per night (USD)
VRBO
From $262 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 $262 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Windham getaway!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Perfectly cozy destination in the mountains for a weekend getaway or a family vacation. This condo has everything that y ...
From $254 per night (USD)
VRBO
From $540 per night (USD)
Expedia
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 $540 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Windham family ski home, walking distance to trails and base
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Wake up with a coffee and walk out onto Windham mountain. Enjoy an updated home with a modern kitchen and amenities. A C ...
From $383 per night (USD)
VRBO
From $298 per night (USD)
Expedia
Spacious Townhouse minutes from Village and Slopes with shuttle to mountain
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Spacious 3-Bedroom Townhouse with Sleeping Loft and Wood-Burning Fireplace at Windham Ski Mountain, Min ...
From $298 per night (USD)
Expedia
$Cozy Cabin Getaway in Windham Catskill Mountains\n$
From $460 per night (USD)
VRBO
Cozy Cabin Getaway in Windham Catskill Mountains\n
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
Welcome! You are viewing our cozy 3500-square-foot cabin tucked away on 5.80 acres in the beautiful and scenic hills of ...
From $460 per night (USD)
VRBO
$Stunning A Frame Chalet, Game Rm, 5 min Windham Mt\n\n$
From $675 per night (USD)
Expedia
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)
Expedia

Search Your Destination Now!

Town of Windham Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 287 Rentals