Vacation Rentals in Windham, New York

50 Properties Available

'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort! Private vacation home
'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!
$4329 / night
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6-bedroom SKI Off Chateau at Windham Mountain Club with WiFi Private vacation home
6-bedroom SKI Off Chateau at Windham Mountain Club with WiFi
$2588 / night
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Custom Windham Mtn Villa w\/ Pool, Theater & Views! Villa
Custom Windham Mtn Villa w\/ Pool, Theater & Views!
$1424 / night
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NEW Modern Cabin | 8 Mins From Skiing | Hot Tub Cabin
NEW Modern Cabin | 8 Mins From Skiing | Hot Tub
$1252 / night
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New Pool Plus Hot Tub & EV Charger 5 mins to Skiing at Windham Mountain Private vacation home
New Pool Plus Hot Tub & EV Charger 5 mins to Skiing at Windham Mountain
$1251 / night
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5 Min to Skiing | Hot Tub | Fire Pit | Pool Table Cabin
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
$1244 / night
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Immaculate & Cozy 3 BR at base of Windham Mtn Condo
Immaculate & Cozy 3 BR at base of Windham Mtn
$1213 / night
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All Season Luxury Condo in Windham\/ Ski On - Ski Off Condo
All Season Luxury Condo in Windham\/ Ski On - Ski Off
$1200 / night
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Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter Private vacation home
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
$1095 / night
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40 acres. seasonal rental.Mountain views.sleeps 12+.perfect for 2 families. Private vacation home
40 acres. seasonal rental.Mountain views.sleeps 12+.perfect for 2 families.
$1094 / night
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Luxury 3300 sqft Ski & Golf Chalet,2 fireplaces & Firepit.5 min from Windham Ski Chalet
Luxury 3300 sqft Ski & Golf Chalet,2 fireplaces & Firepit.5 min from Windham Ski
$1093 / night
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Catskill Vineyard Hideaway: Windham's Cozy Retreat - Hot Tub, 8 BRs, Sleeps 22 Private vacation home
Catskill Vineyard Hideaway: Windham's Cozy Retreat - Hot Tub, 8 BRs, Sleeps 22
$1072 / night
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Windham Farmhouse Escape w\/hot tub Agritourism
Windham Farmhouse Escape w\/hot tub
$980 / night
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SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty \/ Pickle Ball. Private vacation home
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty \/ Pickle Ball.
$950 / night
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HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views Private vacation home
HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views
$926 / night
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Black Bear Cabin - Beautiful cabin located 5min from Windham Mtn Resort ! Private vacation home
Black Bear Cabin - Beautiful cabin located 5min from Windham Mtn Resort !
$855 / night
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Chalet nestled right in Windham Mountain's quiet beauty-private access to trails Chalet
Chalet nestled right in Windham Mountain's quiet beauty-private access to trails
$771 / night
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Great Location - Ski In Ski Out Condo+Amenities Condo
Great Location - Ski In Ski Out Condo+Amenities
$700 / night
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Spacious 4-bedroom house in tranquil Windham with AC big deck and fire pit BBQ Private vacation home
Spacious 4-bedroom house in tranquil Windham with AC big deck and fire pit BBQ
$694 / night
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\"Three Pines\" Luxury 6 Bedroom Ski Chalet with Windham Views Chalet
\"Three Pines\" Luxury 6 Bedroom Ski Chalet with Windham Views
$690 / night
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2 Bed Ski-In\/Out Condo Condo
2 Bed Ski-In\/Out Condo
$657 / night
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Luxe Windham - Hot Tub, Views, Firepit, Peloton - 5min to Mountain! Cabin
Luxe Windham - Hot Tub, Views, Firepit, Peloton - 5min to Mountain!
$646 / night
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Spacious 5-bedroom house in marvelous Windham with AC, WiFi & wood burning stove Private vacation home
Spacious 5-bedroom house in marvelous Windham with AC, WiFi & wood burning stove
$608 / night
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5-Star. Luxury Condo, Heated Pool, Hot Tub, Ski in\/out @ Windham Condo
5-Star. Luxury Condo, Heated Pool, Hot Tub, Ski in\/out @ Windham
$600 / night
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Large Catskill townhome steps from skiing w/pool Private vacation home
Large Catskill townhome steps from skiing w/pool
$587 / night
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5 Minutes To Windham Slopes! High End Amenities! Entertainment Galore! Private vacation home
5 Minutes To Windham Slopes! High End Amenities! Entertainment Galore!
$575 / night
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Windham Mountain Chalet with Treehouse sleeps 15, Game Room & fireplace Private vacation home
Windham Mountain Chalet with Treehouse sleeps 15, Game Room & fireplace
$566 / night
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Windham castle with a view & minutes to skiing! Private vacation home
Windham castle with a view & minutes to skiing!
$542 / night
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Ski, Hike & More: Year-Round Gem in Windham Private vacation home
Ski, Hike & More: Year-Round Gem in Windham
$541 / night
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DREAM LOG CABIN 110 Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet Cabin
DREAM LOG CABIN 110 Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet
$525 / night
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****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape! Private vacation home
****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!
$516 / night
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4 Bdrm Home w\/Hot Tub + Mtn. Views @Hotel Vienna Private vacation home
4 Bdrm Home w\/Hot Tub + Mtn. Views @Hotel Vienna
$511 / night
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Waterfront Secluded Log-house w\/Sauna, Games, More, Mins To Town & Activities Cabin
Waterfront Secluded Log-house w\/Sauna, Games, More, Mins To Town & Activities
$509 / night
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Blue Spruce Chalet — Hot Tub, Pet Friendly Chalet
Blue Spruce Chalet — Hot Tub, Pet Friendly
$485 / night
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Simple and Charming A-Frame Cabin Rental in Windham, New York Cabin
Simple and Charming A-Frame Cabin Rental in Windham, New York
$473 / night
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Cozy Windham Getaway Private vacation home
Cozy Windham Getaway
$460 / night
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SKI Slope views, ski 1 mile drive or walk, Golf Course & walk to town. Private vacation home
SKI Slope views, ski 1 mile drive or walk, Golf Course & walk to town.
$450 / night
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Windham Mountain A Frame Ski House with Central A\/C Private vacation home
Windham Mountain A Frame Ski House with Central A\/C
$450 / night
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Near Hunter and Windham ski resorts. Crystal Pond town house, 4BR & 3.5 bath Condo
Near Hunter and Windham ski resorts. Crystal Pond town house, 4BR & 3.5 bath
$411 / night
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Catskills Retreat - 3Br with 3 En Suites - Near Windham & Wedding Venues Private vacation home
Catskills Retreat - 3Br with 3 En Suites - Near Windham & Wedding Venues
$404 / night
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Cozy Cabin Getaway in Windham Catskill Mountains\n Cabin
Cozy Cabin Getaway in Windham Catskill Mountains\n
$400 / night
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Your Windham Fall and Winter Escape Awaits! Private vacation home
Your Windham Fall and Winter Escape Awaits!
$400 / night
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Mountain View Ski Minutes to Windham & Hunter Cabin
Mountain View Ski Minutes to Windham & Hunter
$386 / night
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CONVENIENT!Walk 1000ft. to Windham Mtn! Fully furnished 2BR\/2Bth Condo w\/WiFi Private vacation home
CONVENIENT!Walk 1000ft. to Windham Mtn! Fully furnished 2BR\/2Bth Condo w\/WiFi
$370 / night
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2 Mi to Windham Mountain: Scenic Home w/ Fire Pit! Private vacation home
2 Mi to Windham Mountain: Scenic Home w/ Fire Pit!
$361 / night
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Cozy townhouse steps away from Windham Mountain- zip code 12496 Private vacation home
Cozy townhouse steps away from Windham Mountain- zip code 12496
$351 / night
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Ski, Hike & Golf: Pet-Friendly Windham Retreat Private vacation home
Ski, Hike & Golf: Pet-Friendly Windham Retreat
$333 / night
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Windham Mountain Vacation Rental ~ 3 Mi to Lifts! Private vacation home
Windham Mountain Vacation Rental ~ 3 Mi to Lifts!
$317 / night
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Presidential Suite with Jacuzzi, Full Kitchen and Sauna near Windham Mtn Condo
Presidential Suite with Jacuzzi, Full Kitchen and Sauna near Windham Mtn
$310 / night
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Windham Family Getaway Private vacation home
Windham Family Getaway
$279 / night
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