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 $384 per night (USD)
Expedia
Windham Chalet with BBQ Hut, Pizza Oven and Hot tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The chalet is located 5 minutes from Windham on a cul-de-sac and has neighbors on one side and state land on the other, ...
From $384 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Cutest Cabin Spring Skiing & Hiking it's BBQ Time!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Cutest Cabin is the perfect stay for 2 people! Located only minutes away to the ski slope-snow tubing & town. Acros ...
From $216 per night (USD)
VRBO
From $1109 per night (USD)
Expedia
Stanley's Mountain Getaway · 5 Min to Skiing | Hot Tub | Fire Pit | Games | Bar
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Make lasting memories in this 5 BR, 3.5 BA, 5,600 ft² cabin in scenic Windham, NY located just 5 min away from Windham M ...
From $1109 per night (USD)
Expedia
$Windham Mtn! 2BR\/2B, Sleeps 6-8. Wi-Fi. Ski, Fine Dining, Hike, Antiquing, More!$
From $264 per night (USD)
VRBO
Windham Mtn! 2BR\/2B, Sleeps 6-8. Wi-Fi. Ski, Fine Dining, Hike, Antiquing, More!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Private WiFi for Internet & cell calling. ========================================= QUADS CONDOMINIUM: 2 bedroom, 2 ba ...
From $264 per night (USD)
VRBO
From $521 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 $521 per night (USD)
Expedia
From $175 per night (USD)
VRBO
Catskills Home, 5 Mins to Windham Mtn Resort!
Bedrooms:
2
Bathrooms:
4
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 $175 per night (USD)
VRBO
$Slope Views: Luxe Windham Retreat w\/ Hot Tub!$
From $484 per night (USD)
Expedia
Slope Views: Luxe Windham Retreat w\/ Hot Tub!
Bedrooms:
3
Bathrooms:
6
Sleeps:
17
Multiple Living Spaces | Outdoor Entertainment Area | Windham Mountain Ski Resort Local wineries, delicious eateries, a ...
From $484 per night (USD)
Expedia
$'The Mountain House:' Windham Retreat w\/ Hot Tub!$
From $627 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 $627 per night (USD)
VRBO
Click For Pricing
Expedia
Catskills House: 1 Mi to Windham Mountain Resort!
Bedrooms:
2
Bathrooms:
8
Sleeps:
10
Welcome to the Catskills region, full of scenic mountain views and outdoor adventure! With 6 bedrooms and 2 bathrooms, t ...
Click For Pricing
Expedia
From $256 per night (USD)
VRBO
Relaxing Catskills Apt < 3 Mi to Windham Mountain!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Experience year-round adventures at this family-friendly home in the heart of Upstate New York! Boasting 2 bedrooms, 2 b ...
From $256 per night (USD)
VRBO
$Spacious Apt w\/ Yard: 3 Mi to Windham Mountain$
From $259 per night (USD)
Expedia
Spacious Apt w\/ Yard: 3 Mi to Windham Mountain
Bedrooms:
2
Bathrooms:
3
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 $259 per night (USD)
Expedia
From $854 per night (USD)
VRBO
Condo in Windham Mountain Village
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Spacious condo for family and friends in WMV, large open space , indoor fireplace , hassle free , steps from the slope, ...
From $854 per night (USD)
VRBO
$Luxury Home w\/ Deck: Explore the Catskill Mtns!$
From $609 per night (USD)
Expedia
Luxury Home w\/ Deck: Explore the Catskill Mtns!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to the Catskills with this Windham vacation rental! Boasting an open living space, stone fireplace, and fully equ ...
From $609 per night (USD)
Expedia
From $1625 per night (USD)
VRBO
Windham Private heated indoor pool.
Bedrooms:
3
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
$NEW 5 Bed 5 1\/2 Bath Townhouse Walk To Skiing! 900 sq ft Of Mountan View Decks!$
From $1026 per night (USD)
Expedia
NEW 5 Bed 5 1\/2 Bath Townhouse Walk To Skiing! 900 sq ft Of Mountan View Decks!
Bedrooms:
6
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 $1026 per night (USD)
Expedia
$Ski Mountain Chalet w\/ Hot tub, Fireplace, Game Room -Windham Mountain$
From $1016 per night (USD)
VRBO
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 $1016 per night (USD)
VRBO
From $526 per night (USD)
Expedia
Luxurious Mountain Retreat: Sauna, Hot Tub, Fire Pit & Park
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience an Inviting Mountain Retreat Escape to our 4BR, 2BA log home situated on a park-like property near Windham an ...
From $526 per night (USD)
Expedia
From $350 per night (USD)
VRBO
Townhouse Spring Skiing & Hiking it's BBQ Time!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Red Fox Townhouse is located in Windham! ...
From $350 per night (USD)
VRBO
From $1517 per night (USD)
Expedia
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)
Expedia
$Stylish Mountain Escape w\/ Hot Tub, 3 Miles to Ski$
Click For Pricing
VRBO
Stylish Mountain Escape w\/ Hot Tub, 3 Miles to Ski
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape the noise of the city and experience pure Catskill bliss at this deluxe 3-bedroom, 2-bathroom home! Ideally situa ...
Click For Pricing
VRBO
$Cozy Catskills Getaway w\/ Yard & Mtn Views!$
From $256 per night (USD)
Expedia
Cozy Catskills Getaway w\/ Yard & Mtn Views!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Surrounded by stellar mountain views and endless all-season adventure, this vacation rental is an ideal spot to jumpstar ...
From $256 per night (USD)
Expedia
From $232 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 $232 per night (USD)
VRBO
$Windham Ridge Townhouse w\/ Beautiful Views - Seasonal Rental$
Click For Pricing
Expedia
Windham Ridge Townhouse w\/ Beautiful Views - Seasonal Rental
Bedrooms:
3
Bathrooms:
4
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 $298 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 $298 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Redwood Retreat in Windham - Pool! Tennis!
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 $205 per night (USD)
Expedia
From $710 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 $710 per night (USD)
VRBO
$TOWNHOUSE-Slp 8 Mt View\/6 BEDS. Downtown Windham. Walk to restaurants and stores$
From $197 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 $197 per night (USD)
Expedia
From $1346 per night (USD)
VRBO
ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!
Bedrooms:
4
Bathrooms:
5
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 $1346 per night (USD)
VRBO
$NEW 5 Bed 5 1\/2 Bath Townhouse Walk To Skiing! 900 sq ft Of Mountan View Decks!$
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:
6
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 $292 per night (USD)
VRBO
Near Skiing & Hiking: Immaculate Windham Getaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Ample Outdoor Space | 4 Miles to Windham Mountain Resort | Near Colgate Lake Just minutes from Windham, NY, this pristi ...
From $292 per night (USD)
VRBO
$Pet-Friendly New York Cabin w\/ Hot Tub & Game Room$
From $492 per night (USD)
Expedia
Pet-Friendly New York Cabin w\/ Hot Tub & Game Room
Bedrooms:
3
Bathrooms:
5
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 $492 per night (USD)
Expedia
From $174 per night (USD)
VRBO
Cozy Catskill Condo - 2 Mi to Windham Mountain Ski
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A 2-bedroom, 1-bathroom condo sitting only 2.2 miles from the Windham Mountain ski area, this Windham vacation rental ma ...
From $174 per night (USD)
VRBO
From $794 per night (USD)
Expedia
WINDHAM HOME SLEEPS 10 - 1 MILE TO SLOPES !
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Location, Location, Location - This conveniently located home has you positioned close to all Windham has to offer. 1 mi ...
From $794 per night (USD)
Expedia
From $191 per night (USD)
VRBO
High Peak Heaven: Cozy Log Cabin on 1 Acre!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Nestled in the Catskill Mountains, this Windham 2-bedroom, 1.5-bath vacation rental cabin makes for the perfect retreat ...
From $191 per night (USD)
VRBO
From $227 per night (USD)
Expedia
Homey Windham Condo: Hike & Ski the Catskill Mtns!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Get outdoors in the Catskill Mountains with a trip to this 2-bedroom, 1-bathroom Windham vacation rental! Windham Mounta ...
From $227 per night (USD)
Expedia
$Condo w\/ Loft: 2 Mi to Windham Mountain Ski!$
From $238 per night (USD)
VRBO
Condo w\/ Loft: 2 Mi to Windham Mountain Ski!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Get away from the hustle and bustle of city life with a retreat to this 2-bedroom, 1-bath Windham vacation rental! The c ...
From $238 per night (USD)
VRBO
From $203 per night (USD)
Expedia
On the Mountain in Windham, New York in the Catskills
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
4 bedroom, 2 1/2 bath home with renovated kitchen and new baths. Outdoor deck with beautiful views. Master Bedroom wit ...
From $203 per night (USD)
Expedia
From $162 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 $162 per night (USD)
VRBO
From $591 per night (USD)
Expedia
ON MTN!Welcome to our Windham MTN Escape! AVAILABLE for 2025 season Dec-Mar
Bedrooms:
4
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 $591 per night (USD)
Expedia
From $407 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 $407 per night (USD)
VRBO
$Mountain Escape 5 Minutes to Ski Resort\n\n\nGreat Discounted Summer rental !$
From $413 per night (USD)
Expedia
Mountain Escape 5 Minutes to Ski Resort\n\n\nGreat Discounted Summer rental !
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
A 2,700 square foot modern well stocked home with incredible views of Windham mountain. Ski Windham is only 1.5 miles aw ...
From $413 per night (USD)
Expedia
$Peaceful Catskills Condo w\/ Deck + Mountain View!$
From $194 per night (USD)
VRBO
Peaceful Catskills Condo w\/ Deck + Mountain View!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Trade in city crowds for a mountain adventure with this Windham vacation rental as your home base! Perched on a hill ove ...
From $194 per night (USD)
VRBO
From $698 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 $698 per night (USD)
Expedia
From $757 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 $757 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 $775 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 $775 per night (USD)
VRBO
From $313 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 $313 per night (USD)
Expedia
$Windham Farmhouse Escape w\/hot tub$
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 $380 per night (USD)
Expedia
NEW - Cozy Modern Home: Stunning views, 3 mins ski,BBQ,Fire Pit,Games, walk dwtn
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 $380 per night (USD)
Expedia
From $338 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 $338 per night (USD)
VRBO
$SKI-IN\/SKI-OUT ON WONDERAMA RUN, 4 BEDROOM, 3 BATH RETREAT$
From $1035 per night (USD)
Expedia
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)
Expedia
From $1431 per night (USD)
VRBO
Serendipity Lake House on Lake Heloise. Beautiful private 4000 sq ft lodge
Bedrooms:
3
Bathrooms:
4
Sleeps:
15
Enjoy a relaxing stay at this gorgeous rustic lodge on 10 acres abutting a 28 acre lake surrounded bybover 300 avrea of ...
From $1431 per night (USD)
VRBO
From $183 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 $183 per night (USD)
Expedia
From $411 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 $411 per night (USD)
VRBO
From $270 per night (USD)
Expedia
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)
Expedia
From $277 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 $277 per night (USD)
VRBO
From $318 per night (USD)
Expedia
Catskills Townhome ~ 2 Mi to Windham Mountain Club
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the stunning beauty of Windham, New York, at this picturesque 3-bedroom, 3-bathroom vacation rental. With bre ...
From $318 per night (USD)
Expedia
$BRAND NEW completely renovated house in Windham, 5 bed\/ 3 bath$
From $983 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 $983 per night (USD)
VRBO
From $378 per night (USD)
Expedia
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 $378 per night (USD)
Expedia
From $1230 per night (USD)
VRBO
Après Chalet|Ski|Luxury|Sauna|HotTub|Firepit|Disco
Bedrooms:
5
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 $1230 per night (USD)
VRBO
From $747 per night (USD)
Expedia
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)
Expedia
From $366 per night (USD)
VRBO
Cozy Mtn-View Chalet < 2 Mi to Windham Slopes
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Private Hot Tub | Scenic Fireside Setting | Easy Access to Windham & Hunter Mountain Skiing There's no shortage of scen ...
From $366 per night (USD)
VRBO
From $937 per night (USD)
Expedia
Reduced May Rates - Plus Special Culinary Promotion! Details Below!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Breathtaking Design, Newly Constructed Farmhouse with Wooded Views in Windham NY ** Special May Culinary Promotion! ** ...
From $937 per night (USD)
Expedia
From $308 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 $308 per night (USD)
VRBO
From $574 per night (USD)
Expedia
Walk to Ski Lift: Family-Friendly Windham Townhome
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Private Hot Tub | Pets Welcome w/ Fee | Near Hiking & Biking Experience the Catskills' year-round natural beauty at thi ...
From $574 per night (USD)
Expedia
$Contemporary Renovated Retreat with Mountain Views, Ski-In\/Ski-Out,...$
From $988 per night (USD)
VRBO
Contemporary Renovated Retreat with Mountain Views, Ski-In\/Ski-Out,...
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Windham Mountainside Marvel Contemporary Renovated Retreat with Mountain Views, Ski-In/Ski-Out, Spacious Living Spaces ...
From $988 per night (USD)
VRBO
From $580 per night (USD)
Expedia
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 $580 per night (USD)
Expedia
From $696 per night (USD)
VRBO
Drift Haus|4.5BR+ Mountain Lodge
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Escape the ordinary at this spacious alpine lodge in the heart of Windham. Tucked into a quiet wooded setting, this five ...
From $696 per night (USD)
VRBO
From $254 per night (USD)
Expedia
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 $254 per night (USD)
Expedia
From $535 per night (USD)
VRBO
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 $535 per night (USD)
VRBO
From $441 per night (USD)
Expedia
Serene Catskills Riverfront Cabin. 3+ Private Acres, HotTub, Deck, Views!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Peaceful mountain retreat where nature meets comfort. Set on 3 private acres with a river running through and direct acc ...
From $441 per night (USD)
Expedia
From $563 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 $563 per night (USD)
VRBO
From $318 per night (USD)
Expedia
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 $318 per night (USD)
Expedia
From $638 per night (USD)
VRBO
Cozy Rustic Bliss Seconds from Windham Mt Resort
Bedrooms:
3
Bathrooms:
6
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 $638 per night (USD)
VRBO
$Retro Retreat: Charming Home w\/Hot Tub & Fire Pit$
From $352 per night (USD)
Expedia
Retro Retreat: Charming Home w\/Hot Tub & Fire Pit
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Nestled on spacious land just 3 miles from Windham Mt and 12 mins to Hunter Mt, this 1970s ski chalet will prov ...
From $352 per night (USD)
Expedia
From $222 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 $222 per night (USD)
VRBO
From $760 per night (USD)
Expedia
Luxurious Home & Amazing Views
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Summary: Whether you're seeking a peaceful escape or exciting adventure, this luxurious home is the perfect getaway!This ...
From $760 per night (USD)
Expedia
From $238 per night (USD)
VRBO
Ski, Hike,Bike,Golf, Dine within a 6 min Drive. Perfect for a Family getaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gorgeous, newly renovated, corner unit with L shaped deck,2 bedroom, 2 bath with picturesque views featuring main level ...
From $238 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Cozy renovated home, ideal for skiing and hiking in Catskills
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
A recently renovated Dutch farmhouse style house will charm you with its modern yet traditional feel and perfect locatio ...
From $255 per night (USD)
Expedia
From $270 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 $270 per night (USD)
VRBO
From $535 per night (USD)
Expedia
4 SEASON VACATION RENTAL
Bedrooms:
3
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 $535 per night (USD)
Expedia
$Charming Mountain Retreat Lg Mod\/Kit on Stream\/Fire-pit\/Hot Tub$
From $381 per night (USD)
VRBO
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 $381 per night (USD)
VRBO
From $491 per night (USD)
Expedia
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 $491 per night (USD)
Expedia
From $1100 per night (USD)
VRBO
Summer at Windham Mountain! On mountain 5 bedroom Retreat!
Bedrooms:
4
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 $544 per night (USD)
Expedia
*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 $544 per night (USD)
Expedia
From $521 per night (USD)
VRBO
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 $521 per night (USD)
VRBO
$Windham\/Hunter All-season French Country Farmhouse-Ultimate in Relaxed Elegance!$
From $775 per night (USD)
Expedia
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 $775 per night (USD)
Expedia
From $820 per night (USD)
VRBO
Chalet nestled right in Windham Mountain's quiet beauty-private access to trails
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
*WELCOMING INQUIRIES FOR SKI SEASON 2025-26, and SUMMER-FALL GUESTS!!!** Perfect Windham Mountain slope side chalet. ...
From $820 per night (USD)
VRBO
From $1315 per night (USD)
Expedia
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)
Expedia
From $469 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 $469 per night (USD)
VRBO
From $854 per night (USD)
Expedia
Stunning Chalet style home with 8 Person Hot Tub, Fire pit & Sauna & steam rm.
Bedrooms:
4
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)
Expedia
From $786 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 $786 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Cozy Caboose in the city
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy, restored 1922 Caboose for rent in the center of downtown Windham...walking distance to restaurants, bars, shops, b ...
From $200 per night (USD)
Expedia
$Waterfront Secluded Log-house w\/Sauna, Games, More, Mins To Town & Activities$
From $562 per night (USD)
VRBO
Waterfront Secluded Log-house w\/Sauna, Games, More, Mins To Town & Activities
Bedrooms:
3
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 $562 per night (USD)
VRBO
From $996 per night (USD)
Expedia
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 $996 per night (USD)
Expedia
From $117 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 $117 per night (USD)
VRBO
$NEW - Gorgeous Modern Lodge w\/ Mt View - 5 Min to Skiing$
From $893 per night (USD)
Expedia
NEW - Gorgeous Modern Lodge w\/ Mt View - 5 Min to Skiing
Bedrooms:
4
Bathrooms:
5
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 $893 per night (USD)
Expedia
From $301 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 $301 per night (USD)
VRBO
$Windham\/Hunter Chalet with breathtaking views$
From $443 per night (USD)
Expedia
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)
Expedia

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Results: 299 Rentals