Vacation Rentals By Owner In Windham, NY

$594.0

Luxury Ski-in Ski-Out Condo + Amenities

Windham, New York, United States

For long term and/or seasonal rental inquiries, please message me (contact info on HiChee.com)brbrbrThis Whisper Creek condo is located in the newest luxury building at Windham, with a heated outdoor swimming pool, two hot tubs, gym, a patio with a fire pit with plenty of outdoor seating, indoor parking, and a ski locker room that opens right out onto the mountain. There is a state-of-the-art fitness room as well as a dedicated private locker for ski equipment with boot warmers.brbrThis unit features a master bedroom with a king-sized bed, a second bedroom with a queen bed, and a third bedroom with two bunk beds. Each of the bedrooms includes a full bathroom en suite. All bedrooms have smart TVs with YouTube tv. The fully equipped kitchen includes everything you will need. There is also a dishwasher and washer/ dryer in the unit. All mattresses are memory foam - Casper or Nova Foam. There is plenty of room for two families. Max of 8 people (4 adults and 4 children). brbrNo pets allowed. Must be at least 25 years old to book reservation.

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Sleeps

$1478.51

/ Nightly

Private Vacation Home

Luxe 8BR Windham Lodge | Theater, Walk to Slopes

Windham, New York, United States

Unwind at Wanderwood Lodge, an 8BR retreat steps from the slopes at Windham Mountain. Cozy up by wood-burning fireplaces, enjoy movie nights in the home theater, or grill with mountain views on the terrace. With fast Wi-Fi, a chef’s kitchen, and room for 20, it’s ideal for families or group getaways. Just minutes from hiking, skiing, and top dining spots—your perfect Catskills escape awaits.br ✔ Walk to Slopesbr ✔ Home Theater Roombr ✔ Fireplacesbr ✔ Wi-Fibr ✔ Full Kitchenbr ✔ Free Easy ParkingbrbrWelcome to Wanderwood Lodge, a premier luxury escape just steps from Windham Mountain`s slopes. This expansive 8-bedroom, 6-bath retreat spans nearly 6,900 square feet and is perfectly designed for families, friends, or groups seeking comfort, connection, and year-round adventure in the Catskills.brbrFrom the comfort of the property, you’ll have a front-row seat to Windham Mountain’s spectacular fireworks, which usually happen on July 4th, New Year’s Eve, and Presidents’ Day weekend. Gather with family and friends, cozy up, and enjoy the show without ever leaving home.brbrStep inside the grand great room, where soaring 20-foot ceilings, exposed beams, and a floor-to-ceiling wall of windows frame serene mountain views. A striking stone fireplace, and spacious sectional invite cozy gatherings, while adjacent dining areas offer seating for large groups beneath natural wood finishes, and abundant light.brbrThe fully equipped kitchen features premium Viking appliances, dual dishwashers, and a decorative ski-themed tile mural over the range. It`s the ideal setup for preparing group meals, with plenty of storage, and counter space for entertaining. Two generous dining areas ensure everyone can enjoy meals together with a view.brbrDownstairs, a dedicated home theater awaits with leather recliners, a stone fireplace, and a wall-mounted TV—perfect for movie nights after a day on the slopes. Throughout the home, rustic finishes and thoughtful layout foster both relaxation and social connection.brbrEnjoy walk-to-slopes access — the White Way trail at Windham Mountain is just across the street, or simply take in the fresh air from multiple balconies and the spacious terrace. Whether you`re here to ski, hike, or simply unwind in nature, Wanderwood Lodge offers a rare blend of luxury and location.brbrWith high-speed Wi-Fi, central air, satellite TV, and onsite parking, every detail has been considered to ensure a comfortable, connected stay—no matter the season.brbrKitchen :brbrThis spacious and well-appointed kitchen blends rustic charm with functionality. Featuring custom wood cabinetry, granite countertops, and a large center island with bar seating, it`s ideal for preparing meals and gathering as a group. The Viking stove is framed by a decorative tile mural depicting a skier, adding a distinctive mountain touch. Additional highlights include dual dishwashers, a double-door stainless steel refrigerator, built-in microwave, toaster, coffee maker, and a farmhouse-style sink set beneath a wide window with woodland views. Everything is designed for convenience and comfort, making it easy to cook for a crowd or enjoy casual breakfasts before hitting the slopes.brbrLiving & Dining Area:brbrThe expansive open-plan living and dining area is the heart of the home, anchored by a dramatic floor-to-ceiling stone fireplace and surrounded by two-story walls of windows that flood the space with natural light. A combination of plush sectional seating, leather sofas, and classic armchairs offer ample room for the entire group to relax in comfort. Adjacent to the sitting area are two formal dining tables—each comfortably seating ten—perfect for shared meals or game nights. Wood-paneled ceilings with exposed beams, antler chandeliers, and large glass doors leading to the deck add a rustic elegance that enhances the mountain lodge atmosphere. Whether you`re warming by the fire, enjoying a meal with a view, or taking in the wooded surroundings, this space offers both grandeur and warmth in equal measure.brbrSleeping Arrangements – 8 BedroomsbrbrWanderwood Lodge features eight spacious bedrooms designed for comfort, privacy, and restful nights. Six bedrooms are furnished with king-size beds, making them ideal for couples or solo travelers seeking a plush retreat. Two additional bedrooms offer bunk bed configurations, perfect for children or groups. Each room reflects the home`s rustic mountain charm with wood accents, cozy bedding, and ample natural light. Bedrooms are spread across multiple levels to accommodate larger parties while still allowing for privacy and quiet. All are located within easy access to the home’s six full bathrooms, ensuring convenience for guests. Whether you`re settling in after a day on the slopes or enjoying a peaceful morning with a view, these bedrooms offer a tranquil space to recharge.brbrHome Theater Description:brbrThe lower-level home theater offers a cozy retreat for movie lovers and groups looking to unwind after a day on the mountain. Outfitted with a full row of plush leather recliners and positioned in front of a large wall-mounted TV, this space is designed for immersive viewing. A stone fireplace adds warmth and ambiance, while the wood-paneled walls and natural tones echo the rustic character found throughout the home. Whether it`s a family film night or catching up on your favorite series, this dedicated space makes entertainment easy and inviting.brbrDeck :brbrStep out onto the expansive deck and take in sweeping mountain views just beyond the treetops. Accessible directly from the main living area, this outdoor space offers a peaceful setting to enjoy your morning coffee or evening glass of wine. Surrounded by rustic wood railings and overlooking Windham Mountain, the deck provides a front-row seat to every season—lush greenery in summer, fiery foliage in fall, and snow-covered slopes in winter. Whether you`re grilling, gathering, or simply soaking in the quiet, the deck is an ideal extension of the lodge’s serene mountain atmosphere.brbrGuests have exclusive access of the grounds and home.brbrAvailable by platform message.brbrNestled in the heart of the Northern Catskills, Wanderwood Lodge offers an unbeatable location for outdoor adventure and mountain relaxation. Just steps from Windham Mountain’s White Way Trail, guests enjoy walk-to-slopes access in the winter and a front-row seat to lush hiking and biking trails in warmer months. The area blends small-town charm with natural beauty, making it a perfect year-round destination.brbrIn under 10 minutes, explore Windham’s welcoming downtown with its boutique shops, farm-to-table restaurants, cozy cafés, and breweries. For outdoor lovers, nearby trails, waterfalls, and scenic overlooks provide endless exploration. During summer and fall, the region comes alive with festivals, farmers markets, and harvest events.brbrWhether you’re here to hit the slopes, take in fall foliage, or simply unplug and enjoy the quiet of the mountains, this area has something for everyone—from families and friend groups to romantic getaways and solo retreats.brbrNearby Attractions:brbrWindham Mountain Resort (5 min)brbrWindham Country Club (5 min)brbrThe Windham Path (5–10 min)brbrWindham Vineyards and Winery (10 min)brbrHunter Mountain (20–25 min)brbrKaaterskill Falls (25–30 min)brbrNorth-South Lake Recreation Area (30–35 min)brbrZoom Flume Water Park (30–35 min)brbrThomas Cole National Historic Site (40–45 min)brbrOlana State Historic Site (45–50 min)brbrNearby Dining:brbrMulligan`s Pub at Windham Country Club (5 min)brbrThe Windham Local (5–10 min)brbrTaphouse Grille (5–10 min)brbrBrandywine Restaurant (5–10 min)brbrUnion + Post (5–10 min)brbrBabblers Café & Lounge (5–10 min)brbrChicken Run (10–15 min)brbrMatilda (10–15 min)brbrJessie’s Harvest House (20–25 min)brbrThe only way to access Wanderwood Lodge is by car, and we highly recommend using a 4WD or AWD vehicle, especially during the winter months when snow and ice are common in the Catskills. The property offers ample on-site parking, making it easy for multiple vehicles to park safely.brbrOnce you`re here, everything from Windham Mountain Resort to local shops, restaurants, and hiking trails is just a short drive away, making it easy to explore the best of the Catskills at your own pace.brbrTo comply with insurance requirements, we kindly ask all guests to sign a rental agreement prior to arrival. Local guests must contact us before booking, and we do not permit third-party reservations. For safety reasons, EV charging is not allowed on the property. After your booking is confirmed, you`ll receive access to our digital guidebook containing Wi-Fi credentials, check-in instructions, and other useful details. We`re here to support you throughout your stay—please reach out with any questions or concerns.brbrBed Configuration (8 Bedrooms Total):brbrTop Level:br3 bedroomsbrEach has a king-size bedbr2 full bathrooms (shared on this floor)brbrMiddle Level:br2 bedroomsbr1 king-size bed (with en-suite bathroom)br1 queen-size bedbr2 bathroom total on this floor (1 shared)brbrBottom Level:br3 bedroomsbr2 rooms with bunk bedsbr1 room with a king-size bedbr2 full bathrooms (shared by all rooms on this level)brAccurate Guest Count: All guests must be listed on the reservation. No unregistered guests are allowed at any time.brbrbrNo Parties or Events: This home is designed for quiet enjoyment. Parties, events, and large gatherings are not permitted under any circumstances.brbrbrLocal Guests & Third-Party Bookings: Local residents must contact us before booking. Third-party reservations (bookings made for someone else) are not accepted.brbrbrRoutine Maintenance: Periodic maintenance such as lawn care, snow plowing, or trash collection may occur during your stay. We aim to keep any disruption to a minimum.brbrbrParking: Please park only in the designated parking areas provided on the property. Do not block driveways or other vehicles.brbrbrNo Smoking: Smoking is strictly prohibited anywhere on the premises, including indoors, decks, and surrounding outdoor areas.

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Sleeps

$948.2

/ Nightly

Private Vacation Home

Lux Windham Getaway | Views & Indoor Heated Pool

Windham, New York, United States

Summary:brbrWelcome to your luxury mountain retreat — the perfect blend of high-end comfort and alpine charm. Perched to capture stunning panoramic views of the surrounding ski mountains, this expansive 5-bedroom home is built for unforgettable getaways with family and friends. Whether you're soaking in the indoor heated pool, unwinding by the fire pit under the stars, or enjoying a movie night in the private home theater, every moment here is designed to elevate your stay.brbrbrbrThe Space:brbrWindham SkiChaletbrbrbrbrStep into grandeur with soaring 30-foot ceilings and a living area wrapped in a stunning all-glass wall, giving you uninterrupted views of the mountains and flooding the space with natural light. The open-concept layout flows into a fully decked-out kitchen, featuring high-end appliances, a breakfast bar, and space for a large dining table — perfect for family dinners or group gatherings.brbrbrbrIndoor Heated Pool available year round.brbrbrbrThe home offers 5 beautifully appointed bedrooms:brbrbrbrThree king suites, each with a private ensuite bathroom and direct balcony accessbrbrbrbrOne additional king bedroom with gorgeous views and balcony accessbrbrbrbrA fun-filled bunk room with two Queen-over-Queen bunk beds, ideal for kids or larger groupsbrbrbrbrWith 4.5 bathrooms in total, everyone has space and privacy. The home theater room makes for perfect movie nights, while the indoor heated pool is a year-round luxury. brbrbrbrStep outside to a 180-degree wraparound deck, or head to the patio and backyard, where a cozy fire pit awaits.brbrbrbrHome comes with the Propane Tank Grillbrbrbrbr Every bedroom(except bunk bed room) has its own balcony to soak in the mountain air and breathtaking scenery.brbrbrbrGuest Access:brbrGuests have full private access to the entire home, including all five bedrooms, 4.5 bathrooms, the indoor heated pool, theater room, living area, kitchen and dining space, backyard, fire pit patio, and decks. Self-check-in is available via smart lock, and ample on-site parking is included. High-speed Wi-Fi, laundry facilities, and all essential amenities are provided to make your stay effortless and extraordinary.brbrbrbrInteraction with Guests:brbrGuest can reach out to host anytime via airbnb message

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Sleeps

$332.08

/ Nightly

Private Vacation Home

Windham Mountain Vacation Rental ~ 3 Mi to Lifts!

Windham, New York, United States

Find your next all-season escape at this lovely Catskills vacation rental! Located less than 5 miles from Windham Mountain Ski Resort and Main Street Windham, this 4-bedroom, 2-bathroom townhome provides a perfect location for everything you want to do while you’re in Windham, New York. When you’re visiting in the winter, be sure to hit the slopes and enjoy an après-ski cocktail. In the summer, you’ll have plenty of hikes, golfing, and sightseeing to do! No matter what, you’ll have a great time.brbr-- THE PROPERTY --brbrPet Friendly w/ Fee | Great Mountain Views | brBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Additional Sleeping: Pack ‘n Play brbrINDOOR LIVING: Smart TVs, wood fireplace (wood provided), board games, books, dining table, ceiling fans, piano brOUTDOOR LIVING: Private patio, outdoor dining area, Weber gas grill, outdoor seating brKITCHEN: Cooking basics, Keurig & drip coffee makers, hot water pot, Crockpot, dishwasher, stove/oven, refrigerator, microwave, dishware & flatware, ice maker, spices, toaster ovenbrGENERAL: Free WiFi, baseboard heating, complimentary toiletries, linens & towels, in-unit washer & dryer, iron/board, hair dryer, trash bags & paper towels brFAQ: Pet fee (paid pre-trip), no A/CbrACCESSIBILITY: 2-story home, 3 exterior steps required to enter, 2 bedrooms & 1 full bathroom on 1st floorbrPARKING: Shared parking lot (4 vehicles), free street parkingbrbr-- THE LOCATION --brbrMAIN STREET (0.9 miles): Tap House Grille, Catskill Mountain Country Store, Windham Theatre, Windham Diner, Ze Windham Wine Bar, Millrock Restaurant, Windham Fine Arts, CarvelbrSUMMER ADVENTURE: Windham Mountain (1 mile), The Windham Path (3 miles), Escarpment Trailhead (5 miles), Five State Lookout (9 miles), Mountain Top Arboretum (12 miles), Kaaterskill Falls Trail Head (16 miles)brWINTER WONDERLAND: Windham Mountain Ski Resort (1 mile), Hunter Mountain Resort (11 miles)brPARS + BIRDIES: Windham Country Club (2 miles), Christman’s Windham House (3 miles), High Ridge Club (5 miles)brAIRPORT: Albany International Airport (46 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly with a $25 fee (+ fees & taxes, 2 pets max) br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property is heated but does not offer air conditioning due to the climate br- NOTE: This 2-story home requires 3 exterior steps to enter. While it offers 2 bedrooms and 1 full bathroom on the 1st floor, additional interior stairs are required to access the bedrooms on the 2nd floor

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Select Dates for Price

Private Vacation Home

Windham Mountain Village Townhouse

Windham, New York, United States

Newly Renovated base of the mountain Townhome. Featuring 2 Bedrooms with a sleeping loft. Spacious open concept including a Fire Place, 85 inch TV, Brand New Kitchen and Bathrooms. Glass Sliders that show off a beautiful Windham Mountain View. Indoor community Hot Tub and Pool available at the Clubhouse with Rental.

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Bath

Sleeps

$616.11

/ Nightly

Chalet

Modern 3BR/4BA Windham chalet w/ hot tub, views & mins to ski, bars, dining!

Windham, New York, United States

Escape to Fun, Adventure, and Comfort: Your Dream Mountain Chalet in Windham, NYbrWelcome to Your Perfect Mountain GetawaybrbrNestled amidst the breathtaking beauty of the Catskill Mountains, just five minutes from the slopes of Windham Mountain and a short drive from the trails of Hunter, lies a picture-perfect retreat that combines rustic charm with modern luxury: our Windham Ski Chalet. This exquisite 3-bedroom (plus flexible sleeping spaces), 4-bathroom home is more than just a rental—it’s your launchpad for adventure, your cocoon of comfort, and your unforgettable escape from the everyday grind.brbrWhether you're planning a ski weekend with friends, a cozy family holiday, or a longer seasonal stay, our chalet offers everything you need to feel at home—and more. With its awe-inspiring mountain views, a 6-person outdoor hot tub, private location, and sophisticated interior design, this home was crafted to help you recharge, reconnect, and reimagine what a getaway can be.

3

Bed

4

Bath

11

Sleeps

$1785.53

/ Nightly

Lodge

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

Windham, New York, United States

The Lodge at Dancing Horse Farm is set on an historic farmstead with beautiful mountain views and is just minutes away from Windham Mountain Club and Hunter Mountain Ski and Snowboard Resort. Dancing Horse Farm is the perfect place to escape your day to day life and reset with your family and friends in a beautiful, open space with private access to the farm area and our woodland hiking trails. brbrThe lodge is situated at the end of a long, hemlock lined, private driveway. Once inside the lodge, your group will find great spaces to be together and plenty of bedrooms to spread out and have your own personal space. The main floor has a large kitchen, dining room and great room that is great for gathering groups but cozy and comfortable for any size family or group. Can't go to a your favorite sporting event... Get together this fall for that big football game at our place and watch on our 65 4K HDTV. The first floor has a large common area with a 75 4K HDTV, a pool table and a dart board. There is a large stone patio and a wooden deck with seating and a gas bbq grill to spread out and enjoy the outdoors. There are also 3 firepit areas in the yard with comfy chairs to warm up on a cool night.brbrJust beyond the lodge you can walk down to our barns here at Dancing Horse Farm and say hello to the animals. Beyond the barn area, you can explore the many acres of woods with private walking trails to get back to nature. brbrWhether you are here to ski, snowboard, hang out on the farm, or just escape to nature, the Lodge at Dancing Horse Farm is the place where you will create memories that last a lifetime. Welcome home.brbrbrCheck out our 3D Home Virtual Tour! (copy and paste link into your browser)brwww.zillow.com/view-3d-home/4bed67c0-cfdb-4e28-a9ff-048ce1d46eec setAttribution=mls&wl=truebrbr*Please note that if you are looking for additional space, please inquire about the Caretaker's Apartment. This space is available for you to rent along with the main lodge. This space is never rented to other guests when you rent the main lodge. The Caretaker's Apartment is attached to the main house with a private entrance. It has a kitchen, bathroom, living room, dining area and bedroom. The bedroom has a king bed and the living room has a twin day bed with an additional twin mattress underneath. The two chairs in the living room also fold out into beds. The space can be utilized for a variety of purposes: grandparents, newlyweds, group members that require private quarters, a teenage retreat, dedicated work space for corporate groups... etc. Please see the pictures in the gallery.brbr**To rent the lodge at Dancing Horse Farm, the primary renter must be on site and must be at least 25 years of age. Unfortunately, the property is not available to rent for prom parties, senior school parties, or similar gatherings. A driver's license, state or federal identification is required prior to booking.

Bed

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Sleeps

$1341.0

/ Nightly

Private Vacation Home

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Windham, New York, United States

Among the nicest properties in Windham. Lovely large home nestled quietly on 12 usable acres with bucolic bridle paths joined to hiking trails. A true feel of Tuscany on the property beginning at the front door. 16' Travertine Dining Island and Professional Kitchen. Seats 14. Wolf Oven / 48” Induction Cooktop. Pickleball /Snowshoe or Cross-Country on the property in Winter. Relax in Spa/Hot Tub /Theatre Room. Prepare meals in professional indoor or outdoor kitchens. The daily rental rate is weekday/weekend driven. HighSeason and Holiday weekends may require 3-4 night minimums respectively. Housekeeping is 275 plus a 500 refundable security deposit.brMountain bike to multiple destinations. Adjacent views to 30 acre horse farm, pond and Ski Windham. Wedding package details available to discuss. Wedding video encompasses two (2) contiguous properties. Ask owner for clarification on pricing for each. HighSeason and Holiday weekends require 3 or 4 night minimums respectively. Limited access to lift tickets during non holiday periods.

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Sleeps

$178.2

/ Nightly

Private Vacation Home

2 Bedroom Townhouse in front of Windham Mountain Ski Resort

Windham, New York, United States

This 2 bedroom, 2 bath Townhouse with loft is located at the top of Windham Mt Village a very short easy walking distance from the Windham ski lodge and beginner lifts. The unit sleeps 8 people (max 6 adults + 2 children) total with a master bedroom with Queen Duxiana bed on main floor and 2nd bedroom with 4 bunk beds and a loft with 2 Duxiana twin beds on the upper level. 2 newly rebuilt full baths with showers, fully equipped kitchen, dining area, living area with wood burning fireplace. Firewood is included. Smart TV with cable and wireless internet included. An outdoor deck has a gas grill. Washer and Dryer. Newly installed central wall air conditioning and heating with remote controls. Access to indoor community pool, hot tub and tennis courts when open.

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Sleeps

$281.13

/ Nightly

Cabin

Newly Built 1200sq ft Guest House 4min to Ski & Hiking

Windham, New York, United States

Beautiful newly built 1200 sq ft cozy log guest house, w vaulted ceiling’s and a gas fireplace for a charming indoor experience. Air conditioning for those few warm summer days. A mud room with bench seating and ski storage area. w a heated floor. An outdoor Adirondack chair seating area w a gas fire table for a peaceful outdoor evening surrounded by a serene tree lined environment.

2

Bed

1

Bath

4

Sleeps

$586.44

/ Nightly

Cabin

Arrowhead Aframe / 5-min to Windham Ski / Hot tub / Movie Room / Karaoke

Windham, New York, United States

Welcome to the Upstate Arrowhead! Escape to our newly built and thoughtfully designed A-frame cabin in Windham, nestled in the heart of the Catskills. Perfect for a cozy getaway or mountain adventure, just minutes from skiing, hiking, and town, yet tucked away for total peace and privacy.brbrShare your adventures with us on IG @arrowhead.nybrbrThe spacebrAs you arrive at the spacious parking area, you’re welcomed by soaring trees that surround the property. The home’s high-end exterior stands out, featuring premium siding and a striking black standing-seam metal roof with dormers, skylights, and snow rails for added safety. An expansive wrap-around deck built with premium materials leads to the main entrance or the impressive 16-ft sliding door at the rear and is a perfect perch for a view of the surrounding forest or stargazing at night.brbrInside, enjoy a true a-frame experience with soaring ceilings and walls of windows that flood the home with natural light, highlighting exposed rafters and wide-plank oak flooring throughout. The open kitchen is anchored by a stunning 10-ft island and a long dining table with a banquette, perfect for gathering. Downstairs, a finished basement offers a game room and a dedicated movie theater/karaoke room, with direct access to a private hot tub just outside—perfectly positioned to enjoy the views.brbrGuest accessbrGuests will receive a keypad code directly from VRBO for easy access to the entire A-Frame during their stay.brbrNotes: brbr**A renter's agreement must be signed after bookingbrbr**We have an outdoor security camera in the driveway pointing at the parking lot and a doorbell camera at the front door. We'll only check the camera to confirm that you've arrived and departed, otherwise we'll completely respect your privacy during your trip.brbr**We love all animals but the A-frame is only dog-friendly and kindly ask that you refrain from bringing your young or untrained pups, as they are more likely to scratch or damage the house and furniture.brbrOther things to notebrWell-behaved pets less than 20lb are welcome (subject to approval) with $25 fee (per pet/night) brbr**This is a rural Catskills property. During winter months, snow, ice, and rapidly changing weather conditions are normal and expected. While the driveway is plowed and treated, guests must be comfortable walking on snow and ice, wearing appropriate footwear, and following parking guidance provided. We cannot guarantee completely ice-free outdoor surfaces, and no refunds are issued due to weather conditions beyond our control.brbr**The outdoor dining setup is not available in winter months.brbr**The laundry room is currently under construction. The washer and dryer is available to use but please excuse our appearance of the room at this time. Our rates are currently discounted to reflect this.

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Bath

Sleeps

$543.97

/ Nightly

Private Vacation Home

Gorgeous Windham Retreat With Views Of The Slopes Only 3 Minutes To Town!

Windham, New York, United States

Stunning Windham Log Cabin Retreat! This spacious home has 4 bedrooms and 3 and 1/2 bathrooms. Sleeps 8-10 (1 King, 2 Queens, 3 bunk beds plus pull out queen couch). Includes a loft overlooking the great room. Radiant heated floors throughout the house. Kitchen is fully equipped with stainless steel appliances, pots, pans, etc. Master Bath with whirlpool tub. Full basement with Pool table. Large stone fireplace in the living room. Gorgeous views of the slopes. Only 3 minutes from town. Perfect family retreat! Relax around the firepit and enjoy all the activities that Windham has to offer!

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Bath

Sleeps

$460.29

/ Nightly

Private Vacation Home

Wonderful mountain home for all of your family adventures!

Windham, New York, United States

Welcome to our cozy mountain retreat! Our beautiful and spacious cabin is perfect for your next getaway. Whether you’re planning a family ski trip, leaf peeping adventure, or a weekend away with friends, this cabin has everything you need for a comfortable and enjoyable stay.brbrOur cabin is ideally located minutes away from Windham Mountain, so you can hit the slopes in no time. brbrBook now and experience the best of what the mountains have to offer and get ready for an unforgettable adventure !

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Bath

Sleeps

$1067.4

/ Nightly

Private Vacation Home

Spacious 5BR All-Season Ski-In/Ski-Out Home Modern Renovation & Smart Features

Windham, New York, United States

Experience mountain living at its finest in this ski-on/ski-off, fully renovated 5-bedroom, 4-bathroom home, designed for every season. Whether you’re hosting friends for a lively weekend or seeking a peaceful getaway surrounded by nature, this spacious retreat offers the perfect blend of modern luxury and cozy comfort.brbrInside, you’ll find state-of-the-art appliances, heated bathroom floors, and two inviting great rooms—one upstairs and one downstairs—ideal for entertaining or relaxing after a day on the slopes. The boot room comes complete with a boot warmer to keep your gear ready for the next run.brbrStep outside to the expansive wraparound deck, where you can grill, gather around the firepit, and take in stunning views of the mountain.brbrPerfect for families, couples, or groups, this all-season home offers every comfort you could want—from crisp winter mornings to sun-soaked summer evenings.brbrAddress: 111-2 Clarence D. Lane Road, Winsome Court, Windham, N.Y. 12496.

5

Bed

4

Bath

12

Sleeps

Vacation Rentals By Owner In Windham, NY

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$586.44

$543.97

$460.29

$1067.4

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