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Vacation Rentals near Windham Mountain

19 Resort Drive, Windham, New York 12496
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    Travelers to Windham are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    All 74 Rentals in Windham
    Secluded Charming Water Front Log Home1 / 53
    (6)Very good
    1.9 miles from Windham Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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    *4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw1 / 25
    (42)Excellent
    3.7 miles from Windham Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Mountain House Retreat1 / 26
    (6)Excellent
    3.2 miles from Windham Mountain
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!1 / 79
    (6)Excellent
    2.0 miles from Windham Mountain
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Balcony
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 20, 2020
    My boyfriend and I found this “romantic and magical” Domeo to stay in for a night and it was everything we could ask for. Very cozy and very clean, and definitely lived up to...
    Reviewed March 24, 2019
    This is a great romantic and cozy dome with a beautiful interior with amazing decorations. Every detail in the interior is inexplicably gorgeous. It was also very clean, quiet...
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    About this property
    This is a Must See, One of a kind Geodesic Dome! 12 feet tall! You will love it so much, it will feel like it is forbidden! ;) Beautiful birch work throughout the entire Dome. Truly magical Glamorous Camping (Glamping) experience! Detailed touches placed with love throughout our Domeo....
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    Windham, Catskill Region
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    ***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***1 / 26
    (1)Excellent
    1.2 miles from Windham Mountain
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    Reviewed September 24, 2014
    We rented this house for the July 4th weekend and just loved it. The location is just perfect and very close to a lot of activities. The place is very comfortable and can easily...
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    About this property
    Charming and cozy 2 bedroom/2 bathroom house with gorgeous views of Windham Mountain and the best of both worlds--a 1.5 mile drive to the mountain (10 miles to Hunter) and less than a minute drive to town (10-15 min walk). Situated on a little less than 2 acres of land on Route 23, but set back...
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    Windham, Catskill Region
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental1 / 55
    (7)Excellent
    2.1 miles from Windham Mountain
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed January 13, 2020
    This was perfectly located around the corner from Hunter Mountain and in a small center of town within walking distance to bars and restaurants. The space is quaint, updated...
    Reviewed August 8, 2018
    Ella is the most hospitable host we have met. It was a pleasure to visit Ella's cabin for the second time in two years. Now, there is also a beautiful tent in front of the house...
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    About this property
    CONTACT OWNER IF LOOKING FOR LARGER VACATION RENTAL OR IF the CALENDAR IS BOOKED. We rent other vacation rentals in the Catskills. Cozy, 1 bedroom unit, ideal for a couple. Great for skiers. 3rd person requests considered on case to case basis. Perfect for couples (or couple with a child). Beds:...
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    Windham, Catskill Region
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    3.1 miles from Windham Mountain
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
    • DVD Player
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    • Patio
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable, two-story, 7-room family home on an acre of land. Recently redecorated, new carpeting, new appliances. Master bedroom has king-size bed, 2nd and 3rd bedrooms each have a twin bed. Living Room, separate Dining Room, Kitchen, and Playroom. Full Bath. Front and back porches. Ample...
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    Windham, Catskill Region
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 4
    The Presidential Suite at Brie & Bordeaux1 / 20
    (1)Excellent
    0.6 miles from Windham Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
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    Pet friendly
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    Smoking allowed
    Reviewed October 27, 2015
    Beautiful guesthouse tucked away in Windham, NY. Great view of the mountain from the living and dining room. Guesthouse has full working kitchen, large Presidential Suite with...
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    About this property
    An upscale and contemporary suite located in the heart of the Catskills, above Bistro Brie & Bordeaux, on Main Street, in Windham, NY. Create you getaway weekends, weeks and season stays. The suite has a king bed, queen bed, and one bunk bed. The great room, incorporates the living room with flat...
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    Windham, Catskill Region
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.8 miles from Windham Mountain
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Pet friendly
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    Smoking allowed
    About this property
    2015 Ski Season rental available. Located 5 minutes from Windham Mountain Ski Resort. The apartment features 2 bedrooms, one bath, furnished with quaint country antiques, and new furniture. Spotlessly clean, convent. The kitchen is fully equiped with dishes, utensils, pots, and pans, microwave,...
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    Windham, Catskill Region
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1.8 miles from Windham Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    About this property
    Great views of Windham Mountain and the valley left and right. The house is 1.3 miles from Ski Windham. Large living room/dinning area with birds eye view of mountain and valley from a wraparound deck. Enjoy an adult cocktail watching the New Years Fire works or the stars. BBQ grill on the deck....
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    Windham, Catskill Region
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.8 miles from Windham Mountain
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large beautiful home on 6 acres of land only a couple minutes to Ski Windham Mountain and snow tubing park. Large outdoor fire-pit surrounded by huge rocks with Adirondack chairs. Nice outdoor hot tub. Out side cooking grill and outside deck looking at Ski Windham Mountain. Home has 5 bedrooms...
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    Windham, Catskill Region
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    3.0 miles from Windham Mountain
    8 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Hot Tub
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    • Mountain Views
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Mountain House. Sitting on five beautiful acres with views of 4 of the highest peaks in the Catskills, this is the perfect family getaway spot for all seasons. Ask about All-Inclusive Packages, which can include, on-site concierge, car and chef services and much more! In the winter...
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    Windham, Catskill Region
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 22
    Windham Townhouse - Base of Mountain1 / 18
    (6)Excellent
    0.2 miles from Windham Mountain
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Windham, Catskill Region
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    1.3 miles from Windham Mountain
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    In the land of Rip Van Winkle lies this 20-acre elevated mountain campsite with surrounding pine and cedar trees. Enjoy great views and lots of private space just one mile from the hamlet of Windham, NY. During your camping adventure enjoy platinum member access to Christman's Windham House...
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    Windham, Catskill Region
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
    0.2 miles from Windham Mountain
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Windham, Catskill Region
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    1.6 miles from Windham Mountain
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Windham, Catskill Region
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain1 / 21
    (6)Very good
    2.9 miles from Windham Mountain
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Windham, Catskill Region
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
    Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub1 / 36
    (95)Excellent
    3.3 miles from Windham Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
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    Windham, Catskill Region
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Windham Quads Condo! Ski '20/'21. Scroll to bottom for Rates ⬇️1 / 24
    (118)Very good
    2.2 miles from Windham Mountain
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Housekeeping Included
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    Windham, Catskill Region
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Windham Mountain Getaway 2BD 2BA Condo1 / 27
    (23)Very good
    2.2 miles from Windham Mountain
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
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    Windham, Catskill Region
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Windham:  Ski Season: Wkds & Midweek- High Speed WIFI, Private deck, Watch Video1 / 24
    (77)Excellent
    0.6 miles from Windham Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    ****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!1 / 49
    (28)Excellent
    0.4 miles from Windham Mountain
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    NEW! Luxury Home on Windham Mountain! Walk to Slopes1 / 42
    (13)Very good
    0.5 miles from Windham Mountain
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 11
    Spacious Retreat with Luxurious View1 / 28
    (15)Excellent
    3.6 miles from Windham Mountain
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Windham, Catskill Region
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 16
    Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo1 / 18
    (7)Excellent
    0.2 miles from Windham Mountain
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    • Shared Indoor Pool
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    Windham, Catskill Region
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Windham Mtn.-Walking distance to trail and base lodge!1 / 30
    (38)Excellent
    0.3 miles from Windham Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain1 / 50
    (71)Excellent
    3.2 miles from Windham Mountain
    9 Bedrooms, 5 Bathrooms, Sleeps 30 Quick View
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    Windham, Catskill Region
    Rental Home - 9 Bedrooms, 5 Bathrooms, Sleeps 30
    'New Home' Idyllic  Mt Views ,Pond & Horse farm views 2 min to Town1 / 36
    (15)Excellent
    1.9 miles from Windham Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Housekeeping Included
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    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet1 / 25
    (36)Excellent
    1.5 miles from Windham Mountain
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Windham, Catskill Region
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1.5 miles from Windham Mountain
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Get outdoors in the Catskill Mountains with a trip to this 2-bedroom, 1-bathroom Windham vacation rental! Windham Mountain sits only 2.2 miles from the cozy condo where you can spend the day skiing the slopes. Go for a hike through the Kaaterskill Wild Forest, shop and dine in the Village of...
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    Windham, Catskill Region
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1.5 miles from Windham Mountain
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Get away from the hustle and bustle of city life with a retreat to this 2-bedroom, 1-bath Windham vacation rental! The condo has room for 4 to relax and feel at home with a fully equipped kitchen and extra sleeping space in the loft. Get bundled up for a day skiing the slope of Windham Mountain,...
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    Windham, Catskill Region
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
    0.7 miles from Windham Mountain
    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Terrace
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    About this property
    Welcome to the Catskills region, full of scenic mountain views and outdoor adventure! With 6 bedrooms and 2 bathrooms, this Windham vacation rental offers charming antique finishes, a fully equipped kitchen, and an open interior with ample natural light, ideal for entertaining. Discover rolling...
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    Windham, Catskill Region
    Rental Home - 6 Bedrooms, 2 Bathrooms, Sleeps 10
    0.5 miles from Windham Mountain
    8 Bedrooms, 3 Bathrooms, Sleeps 17 Quick View
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    About this property
    Local wineries, delicious eateries, and all the beauty of the Catskill Mountains will be right at your fingertips at this lovely 5-bed, 3-bath family home. Along with an ideal location within walking distance to everything - including Windham Mountain Resort and Windham’s main drag - this vacation...
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    Windham, Catskill Region
    Rental Home - 8 Bedrooms, 3 Bathrooms, Sleeps 17
    0.7 miles from Windham Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    About this property
    Nestled on a scenic road and overlooking an acre of private land with wooded surroundings, the ‘Windham View’ vacation rental provides a one-of-a-kind Catskills getaway! Built by the current owners, the cabin-style home exudes custom charm and comfort while offering 4 bedrooms, 3 baths, an open...
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    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    0.9 miles from Windham Mountain
    5 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    About this property
    Clear the calendar for a trip to the Catskills and stay at this spacious vacation rental property! With 5 bedrooms and 2 bathrooms, this house is perfect for groups of 13 - whether it be a getaway with friends or grand family retreat! Enjoy a location perched on a peaceful hillside, yet just a mile...
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    Windham, Catskill Region
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 13
    0.8 miles from Windham Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Escape the stress of the city with a hiatus to ‘The Mountain House,’ a 4-bedroom, 2-bathroom vacation rental in Windham! Offering all the essential amenities, a spacious deck with a hot tub, and Windham Mountain views, you’ll be able to enjoy the relaxation you deserve at this incredible home....
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    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Modern Mountain House 5Bd/3Ba, HotTub, 4 Season Room, 5 min from Windham Mtn1 / 20
    (6)Excellent
    2.1 miles from Windham Mountain
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    Windham, Catskill Region
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    2.0 miles from Windham Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Cable/satellite TV
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape the noise of the city and experience pure Catskill bliss at this deluxe 3-bedroom, 2-bathroom home! Ideally situated less than 3 miles from Windham Mountain’s year-round adventure, this vacation rental is the ultimate respite from the stress of daily life. After long days spent on the nearby...
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    Windham, Catskill Region
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Spacious Mountain Escape - Minutes to Windham/Hunter1 / 19
    (1)Excellent
    3.5 miles from Windham Mountain
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Windham, Catskill Region
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    0.5 miles from Windham Mountain
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Waterfront
    • Hot Tub
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    Pet friendly
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    ******NOW ACCEPTING RESERVATION REQUESTS FOR 2021/2022 SKI SEASON****** ***EARLY BOOKING DISCOUNT FOR 21/22 SEASON DATES IF BOOKED BEFORE 6/1/21*** (OCTOBER - JANUARY 4th - DATES STILL AVAILABLE!) Perfect Windham Mountain slope side chalet. Short walk to slopes in winter and bike trails in...
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    Windham, Catskill Region
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Luxury Ski Windham Resort directly on Ski Mountain. Enjoy direct ski in/out1 / 45
    (1)Excellent
    0.6 miles from Windham Mountain
    6 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Balcony
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    Windham, Catskill Region
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 15
    Year-Round Relaxing Mountain Escape1 / 33
    (10)Excellent
    1.8 miles from Windham Mountain
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Windham, Catskill Region
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Winsome Windham - Secluded Chalet with Ski Windham Views1 / 30
    (32)Excellent
    1.9 miles from Windham Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 14
    The perfect mountain getaway nestled in the woods 2 min from downtown Windham.1 / 38
    (20)Excellent
    1.7 miles from Windham Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    • Patio
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    • Terrace
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    Location Information
    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 15
    2.0 miles from Windham Mountain
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Surrounded by stellar mountain views and endless all-season adventure, this vacation rental is an ideal spot to jumpstart your next alpine escape! Boasting cozy living areas and a wood-burning stove, this 2-bedroom, 1-bathroom retreat is well-suited for any outdoor itinerary. Cast a line in the...
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    Windham, Catskill Region
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Escape Winter... above & beyond. Perfect house for family, friends & fresh air.1 / 38
    (22)Excellent
    0.2 miles from Windham Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    • Shared Indoor Pool
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    Smoking allowed
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    Windham, Catskill Region
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Windham Family Getaway (Brand New!)1 / 29
    (22)Excellent
    1.1 miles from Windham Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
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    Smoking allowed
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    Windham, Catskill Region
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    3.8 miles from Windham Mountain
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Terrace
    • Parking
    • Hot Tub
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    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in the breathtaking beauty of the Catskills when you stay at this grand 4-bedroom, 5-bathroom vacation rental. Nestled on 20 acres of wooded land and bordering a running creek, the Windham home makes for the perfect foundation for a relaxing and restorative getaway. Enjoy a warm...
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    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham1 / 15
    (6)Excellent
    0.5 miles from Windham Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • DVD Player
    • Balcony
    • Sauna
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    2.3 miles from Windham Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Grill
    • Balcony
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    • Mountain Views
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the Catskills with this Windham vacation rental! Boasting an open living space, stone fireplace, and fully equipped kitchen, this 4-bedroom, 2-bath home is a modern retreat. Hunter Mountain sits only 10.5 miles away, and Windham Mountain is 3 miles from home, promising winter fun on the...
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    Location Information
    Windham, Catskill Region
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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