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Windham Rentals

From $229 per night (USD)
VRBO
LUXURY DUPLEX SUITE WITH JACUZZI
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 $229 per night (USD)
VRBO
From $306 per night (USD)
Expedia
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step inside and be greeted by a haven of sophistication. The living area boasts a stunning fireplace, casting a warm and ...
From $306 per night (USD)
Expedia
From $270 per night (USD)
VRBO
GLASS MIRROR CABIN - HAUS WINDHAM
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $270 per night (USD)
VRBO
From $456 per night (USD)
Expedia
The Haüs Windham - Luxury 2 Bedroom Suite w Loft
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $456 per night (USD)
Expedia
From $436 per night (USD)
VRBO
NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to Haus Windham - your ultimate luxury vacation rental in Windham, New York, where tranquility and opulence inte ...
From $436 per night (USD)
VRBO
From $225 per night (USD)
VRBO
Guesthouse Minutes from the Mountain!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to our charming guest house, nestled just minutes away from Windham Mountain! This cozy retreat offers ...
From $225 per night (USD)
VRBO
From $536 per night (USD)
VRBO
Luxurious Home & Amazing Views
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Summary: Whether you're seeking a peaceful escape or exciting adventure, this luxurious home is the perfect getaway!This ...
From $536 per night (USD)
VRBO
From $1035 per night (USD)
VRBO
SKI-IN/SKI-OUT ON WONDERAMA RUN, 4 BEDROOM, 3 BATH RETREAT
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
The main level features the kitchen, dining room, wood burning fireplace, den and great room with sun decks and views of ...
From $1035 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Windham Mountain Village Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Welcome to our fantastic Windham Mountain condo, where the location is truly unbeatable! Whether you're seeking ...
From $319 per night (USD)
VRBO
From $602 per night (USD)
VRBO
Cozy Rustic Bliss Seconds from Windham Mt Resort
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Summary: Vacation in this sprawling rustic home. Cook in 2 modern kitchens each with Kuerigs, cozy up by the 1st floor f ...
From $602 per night (USD)
VRBO
From $253 per night (USD)
VRBO
Mountain Cabin with Scenic Views and Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: Come relax at our modern home that is located right in the heart of Windham ! Walking distance to town, local ...
From $253 per night (USD)
VRBO
From $233 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 $233 per night (USD)
Expedia
From $199 per night (USD)
VRBO
Windham Home Near Mountain Biking & Hiking Trails!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This 2-bed, 2-bath vacation rental in Windham is perfect for a small group of friends or family looking to unplug, unwin ...
From $199 per night (USD)
VRBO
From $343 per night (USD)
Expedia
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 $343 per night (USD)
Expedia
From $1105 per night (USD)
VRBO
Brand New Luxury Ski Cabin - 2 Mi to Windham Mtn!
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Witness the breathtaking beauty of the Catskill Mountains at this stunning 6-bed, 5.5-bath vacation rental. Nestled in n ...
From $1105 per night (USD)
VRBO
From $817 per night (USD)
Expedia
Luxury Ski-in Ski-Out 4 Bedroom 10 Bed Condo at Whisper Creek Windham Mountain
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Ski-In / Ski-Out Luxury 4 bedroom, 4 bath, condo at the base of Windham Mountain! Owned and designed primarily for pers ...
From $817 per night (USD)
Expedia
From $1065 per night (USD)
VRBO
Bump Mountain Retreat: Hot Tub, Sauna, Pool, Game Room, Piano & Panoramic Views
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
If you're looking for a luxurious ski retreat a short drive from NYC, then look no further. Perched on a mountainside, B ...
From $1065 per night (USD)
VRBO
Click For Pricing
Expedia
Windham House with Hot Tub perfect for families
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Spacious restored family house just, 1.7 miles from Ski Windham and 6.7 miles from Hunter Mountain. Three large family r ...
Click For Pricing
Expedia
From $567 per night (USD)
VRBO
Luxury Ski-in Ski-Out Condo + Amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Please message me for long term and/or seasonal rental inquiries. This Whisper Creek condo is located in the newest lux ...
From $567 per night (USD)
VRBO
From $1901 per night (USD)
VRBO
Windham ski in-out condo, luxury 2000+ sf modern 5BR, hot tub, pool, boot room++
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
We are renting our 2000+ sf modern, renovated, mountain facing luxury condo at Whisper Creek to someone who will take gr ...
From $1901 per night (USD)
VRBO
From $245 per night (USD)
VRBO
Vacation Rental Home ~ 2 Mi to Windham Mountain!
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Discover the charming town of Windham, NY, and stay at this spacious 3-bedroom, 1.5-bath vacation rental. With a cozy fi ...
From $245 per night (USD)
VRBO
From $1665 per night (USD)
VRBO
Lux Mansion Windham, Catskills Hot Tub, BBQ, Pool Table, Fire pit, Pond
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
SPECIAL OFFER until the end of December! Book 2 nights on weekdays and get 50% off the 3rd night (weekdays only) <b>We ...
From $1665 per night (USD)
VRBO
From $481 per night (USD)
VRBO
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
Bedrooms:
3
Bathrooms:
9
Sleeps:
25
Step into the heartwarming embrace of history at our enchanting 1800's residence! This cherished abode beckons you with ...
From $481 per night (USD)
VRBO
From $1061 per night (USD)
Expedia
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 $1061 per night (USD)
Expedia
From $1245 per night (USD)
VRBO
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 $1245 per night (USD)
VRBO
From $3429 per night (USD)
VRBO
Luxurious ski in/out, 3-story chalet directly on the slopes of Windham Mountain
Bedrooms:
7
Bathrooms:
7
Sleeps:
12
Luxurious ski in/ ski out, three-story chalet located directly on the slopes of Windham Mountain and minutes drive from ...
From $3429 per night (USD)
VRBO
From $546 per night (USD)
VRBO
Red Lift Cabin - Close to town, hiking and biking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Just 2.5 hours from NYC in the heart of the Catskills. One of a kind entirely renovated townhouse. 3 minutes walking dis ...
From $546 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Charming 3 bedroom, 2 bathroom chalet on the mountain!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Well lit, open floor plan, with wood burning fireplace. You'll be staying right on Windham Mountain - so close to skiin ...
From $270 per night (USD)
VRBO
From $270 per night (USD)
VRBO
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)
VRBO
From $1080 per night (USD)
VRBO
Ski-in / Ski-out luxury 3-bedroom Windham condo with outdoor pool and hot-tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Get ready to relax in this 3-bedroom condo in Windham. With 2 king beds and 2 bunk beds, guests will have plenty of spac ...
From $1080 per night (USD)
VRBO
From $396 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 $396 per night (USD)
VRBO
From $934 per night (USD)
VRBO
BRAND NEW completely renovated house in Windham, 5 bed/ 3 bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to our beautiful, cozy mountain retreat! Our beautiful and spacious home is brand new and completely renovated. ...
From $934 per night (USD)
VRBO
From $374 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 $374 per night (USD)
VRBO
From $865 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 $865 per night (USD)
Expedia
From $571 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 $571 per night (USD)
VRBO
From $276 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 $276 per night (USD)
Expedia
From $747 per night (USD)
VRBO
In the Heart of Windham - Best Location
Bedrooms:
3
Bathrooms:
5
Sleeps:
13
Discover this 5-bedroom gem in Windham. This pleasant house features 1 king bed and 4 queen beds, perfect for a group ge ...
From $747 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Cozy Mtn-View Chalet < 2 Mi to Windham Slopes
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Private Hot Tub | Scenic Fireside Setting | Easy Access to Windham & Hunter Mountain Skiing There's no shortage of scen ...
From $347 per night (USD)
Expedia
$LUXURIOUS & SERENE SKI-IN/ SKI-OUT \Winterfell\ LODGE$
From $1929 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 $1929 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $1295 per night (USD)
VRBO
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)
VRBO
From $814 per night (USD)
Expedia
September Special! Choose a complimentary fun experience - see details below!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
September Special! Farmhouse renters [min. 2 nights] enjoy your choice of one complimentary event in our luxury barn or ...
From $814 per night (USD)
Expedia
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
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 $454 per night (USD)
VRBO
Cozy townhouse steps away from Windham Mountain- zip code 12496
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Note: When making vacation reservations, please plan ahead by including lift tickets in your purchase – advanced purchas ...
From $454 per night (USD)
VRBO
From $1472 per night (USD)
Expedia
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 $1472 per night (USD)
Expedia
From $322 per night (USD)
VRBO
Mountain View Ski Minutes to Windham & Hunter
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
At this cozy mountain view cabin, you can wake up minutes from the ski lifts. We are 4 minutes from the ski slopes of Wi ...
From $322 per night (USD)
VRBO
From $267 per night (USD)
Expedia
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 $267 per night (USD)
Expedia
From $814 per night (USD)
VRBO
September Special! Choose a complimentary fun experience - see details below!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
September Special! Farmhouse renters [min. 2 nights] enjoy your choice of one complimentary event in our luxury barn or ...
From $814 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
Click For Pricing
VRBO
Walk to Ski Lift: Family-Friendly Windham Townhome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private Hot Tub | Pets Welcome w/ Fee | Near Hiking & Biking Experience the Catskills' year-round natural beauty at thi ...
Click For Pricing
VRBO
From $937 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 $937 per night (USD)
Expedia
From $814 per night (USD)
VRBO
September Special! Choose a complimentary fun experience - see details below!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
September Special! Farmhouse renters [min. 2 nights] enjoy your choice of one complimentary event in our luxury barn or ...
From $814 per night (USD)
VRBO
From $7018 per night (USD)
Expedia
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 $7018 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Delightful 3-bedroom chalet with WiFi in Windham
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This fabulous chalet in Windham offers a cozy retreat for guests. With 3 bedrooms including a queen, twin, and bunk bed, ...
From $258 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Idyllic Mountain Stay Hot Tub, Wood Stove, Games
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Escape to this stylish mountain retreat, situated on 3 private acres with breathtaking views of Windham + Hunter Mountai ...
From $459 per night (USD)
Expedia
From $448 per night (USD)
VRBO
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)
VRBO
From $508 per night (USD)
VRBO
Serene Catskills Riverfront Chalet. HotTub + Views!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Serene mountain retreat where nature meets comfort. Set on 3 private acres with a river running through and direct acces ...
From $508 per night (USD)
VRBO
From $266 per night (USD)
VRBO
Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
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 $266 per night (USD)
VRBO
From $348 per night (USD)
Expedia
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Escape to Windham in this beautifully designed, pet-friendly home—just a 2-minute walk to the village’s charming shops, ...
From $348 per night (USD)
Expedia
From $350 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 $350 per night (USD)
VRBO
From $456 per night (USD)
Expedia
MIRROR CABIN IN THE FOREST WITH HOT TUB
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Mirror Cabin Retreat | Modern Luxury in the Catskills Discover the ultimate Catskills getaway at this one-of-a-kind mir ...
From $456 per night (USD)
Expedia
From $670 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 $670 per night (USD)
VRBO
From $1620 per night (USD)
Expedia
Family-Friendly Windham Estate, Swimming Pond, Spa
Bedrooms:
6
Bathrooms:
8
Sleeps:
16
Summary: Escape to the ultimate Catskills retreat at The Mountain House! This 8-BR, 6.5-BA home on 10.5 acres features a ...
From $1620 per night (USD)
Expedia
From $340 per night (USD)
VRBO
4-bedroom country house in serene Windham with WiFi, AC
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
This 4-bedroom Center Hall Colonial is perfect for your escape to Windham. With 1 king bed and 3 queen beds, this wonder ...
From $340 per night (USD)
VRBO
Click For Pricing
Expedia
Peaceful 3-BR Getaway Just Outside Windham Town
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Set within Windham’s sought-after Windmont community, this expansive mountain retreat offers privacy, comfort, ...
Click For Pricing
Expedia
From $347 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 $347 per night (USD)
VRBO
From $1000 per night (USD)
Expedia
Fireplaces, Home Theater, Ski-In/Out Windham Lodge
Bedrooms:
6
Bathrooms:
8
Sleeps:
16
Unwind at Wanderwood Lodge, an 8BR retreat with ski-in/ski-out access on Windham Mountain. Cozy up by wood-burning firep ...
From $1000 per night (USD)
Expedia
From $324 per night (USD)
VRBO
3 Mi to Windham Mountain: Private Hilltop Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Stunning Views of Winter Slopes | Hot Tub | Playroom Shed for Kids Plan a mountain getaway the whole family will love — ...
From $324 per night (USD)
VRBO
From $279 per night (USD)
VRBO
Secluded Retreat w Hot Tub in Windham
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Escape to this secluded Catskills retreat! Just minutes from Windham Mountain, Hunter, hiking trails, and lakes ...
From $279 per night (USD)
VRBO
From $755 per night (USD)
VRBO
Unwind Windham, Chalet
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Tucked away in the heart of the Catskills, Unwind Windham is more than just a place to stay—it’s a retreat designed for ...
From $755 per night (USD)
VRBO

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Results: 171 Rentals