Town of Windham Rentals
From $274 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 $274 per night (USD)VRBO
From $250 per night (USD)Expedia
Cutest Cabin in Windham on site miniature golfing with fire pit and BBQ
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Cutest Cabin in Windham is the perfect stay for 2 people! Located only minutes away to it all! On site activities, m ...
From $250 per night (USD)Expedia
From $281 per night (USD)VRBO
Catskills Home, 5 Mins to Windham Mtn Resort!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Make your next trip to the Catskills one to remember when you stay at this 2-bedroom, 2-bath vacation rental! Located on ...
From $281 per night (USD)VRBO
From $635 per night (USD)Expedia
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 $635 per night (USD)Expedia
From $545 per night (USD)VRBO
'The Mountain House:' Windham Retreat w/ Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape the stress of the city with a hiatus to ‘The Mountain House,’ a 4-bedroom, 2-bathroom vacation rental in Windham! ...
From $545 per night (USD)VRBO
From $572 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 $572 per night (USD)Expedia
From $346 per night (USD)VRBO
Relaxing Catskills Apt < 3 Mi to Windham Mountain!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Experience year-round adventures at this family-friendly home in the heart of Upstate New York! Boasting 2 bedrooms, 2 b ...
From $346 per night (USD)VRBO
From $351 per night (USD)Expedia
Spacious Apt w/ Yard: 3 Mi to Windham Mountain
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the heart of Upstate New York, this 2-bedroom, 2-bath apartment offers easy access to Windham’s best summer a ...
From $351 per night (USD)Expedia
From $548 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 $548 per night (USD)VRBO
From $883 per night (USD)VRBO
Luxe Lodge w/ Mt View - Hot Tub, Fire Pit, Game Rm, 5 Min to Skiing
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Plan your all-seasons escape to this beautiful, luxury chalet with direct views of Windham Mt., just a 5 minute drive to ...
From $883 per night (USD)VRBO
From $4054 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 $4054 per night (USD)VRBO
From $982 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 $982 per night (USD)VRBO
From $539 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 $539 per night (USD)VRBO
From $578 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 $578 per night (USD)VRBO
From $537 per night (USD)VRBO
4BR TOWNHOUSE MINUTES TO WINDHAM & HUNTER Free 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 $537 per night (USD)VRBO
From $754 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 $754 per night (USD)VRBO
From $647 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 $647 per night (USD)VRBO
From $475 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 $475 per night (USD)VRBO
From $1727 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 $1727 per night (USD)VRBO
From $481 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 $481 per night (USD)VRBO
From $4920 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 $4920 per night (USD)VRBO
From $559 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 $559 per night (USD)Expedia
From $1255 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 $1255 per night (USD)VRBO
From $230 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 $230 per night (USD)Expedia
From $1482 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 $1482 per night (USD)VRBO
From $2078 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 $2078 per night (USD)Expedia
From $809 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 $809 per night (USD)VRBO
From $386 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 $386 per night (USD)VRBO
From $533 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 $533 per night (USD)VRBO
From $516 per night (USD)Expedia
Windham Immaculate Ski Chalet with Awesome Fire Pit. Available 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 $516 per night (USD)Expedia
From $146 per night (USD)VRBO
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
HIDDEN GEM IN CATSKILLS. Relax in the fresh mountain air! Light-filled cozy studio on Main St in downtown Windham. S ...
From $146 per night (USD)VRBO
From $754 per night (USD)VRBO
MTN RETREAT In Windham
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Private 4BR, 2.5 bath contemporary home is situated on a cul-de-sac in Windham, NY The house has an open floor concept, ...
From $754 per night (USD)VRBO
From $543 per night (USD)VRBO
5 Bedrooms 5 1/2 Bath Ski Area Views, Walk to Skiing, Huge Common Space & Decks!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Unit 3: This brand new 3600 square foot townhome boasts 5 bedroom and 5 1/2 baths directly across from Windham Mountain. ...
From $543 per night (USD)VRBO
From $1665 per night (USD)Expedia
'Sundance Vistas - Log Home ' - 2 Miles From Windham Ski Mountain
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Canadian Log Home on 14 acres yet only 2 miles to Windham Ski Mountain. The house has 4 bedrooms plus a loft and 3 bat ...
From $1665 per night (USD)Expedia