Vacation Home Rentals By Owner In Windham, NY

After a complete renovation we are back and ready to host ! Our condo is perfect for families & friends looking for a great escape without the hassles! Most convenient location in Windham Mountain Village. Enjoy everything and anything the Windham area has to offer. Windham 71 is stocked with everything you could need for a great time. Large dining space, open comfortable floor plan, bunk room downstairs (3 singles, 1 double) and full bathroom with washer/dyer. The master suite (king) with full bathroom and second bedroom room (queen) are upstairs. Pull out couch in living room. Smart TVs/Wifi/air conditioning. Back deck with grill table and chairs to enjoy outdoors. Two Tennis/pickleball courts on premise. Multiple Hiking & biking trails all nearby. There are 3 golf courses in Windham, there are also another 9 golf courses within 20 miles of Windham, including 7 public and 2 private courses. Walkable distance to Windham ski mountain. 20 Minute drive to Hunter Mt., 45 Min. ride to Belleayre Ski Mt. Come home relax enjoy the view the back deck or walk over into the pool house with indoor pool & hot tub.

Above & beyond. Perfect house for family, friends & fresh air.

Windham, New York, United States

Bed

Bath

Sleeps

$427.2

Come relax in our secluded 4 bedroom, 2 bathroom contemporary vacation rental LESS THAN 5 mins from Windham Mt and 15 mins from Hunter! Completely set back from the road and neighbors so you can relax outdoors on the deck and grill, count the stars from the hot tub or enjoy roasting marshmallows with friends around the fire pit. Indoors is a cozy oasis where you can entertain in the kitchen or warm up around the wood burning stove. Close to many amazing restaurants, hiking, skiing, & Vineyard!brThe spacebrThis house is a 4 bedroom 2 bathroom. Downstairs has 3 bedrooms , 1 bathroom. Upstairs has 1 bedroom and 1 bathroom.brGuest accessbrGuests have access to all bedrooms except for the garage and the closet in the master bedroom upstairs which will be locked up with owners private belongings.

Mountain Rental w/ Hot Tub 5 Mins from Windham Mt

Windham, New York, United States

Bed

Bath

Sleeps

$876.92

LISTING DESCRIPTION brA private six-bedroom estate offering upscale comfort and luxury. The property is part of the Dingley Dell Estate, just a six-minute drive from Windham town, and about 25 minutes from Hunter Ski Resort. It features expansive, beautifully landscaped green grounds, excellent outdoor seating areas, a convenient location, and a high level of privacy. The home has been completely renovated to ensure maximum comfort for guests, and includes a pool, movie room and a high-quality sound system.brbrPROPERTY IN DETAILbrWelcome to a spacious and beautifully renovated retreat designed with comfort, relaxation, and unforgettable gatherings in mind. Thoughtfully refurbished from top to bottom, this private property offers the perfect balance of luxury, entertainment, and cozy charm for families, friends, and group getaways.brbrThe home features 6 generously sized bedrooms accommodating up to 14 guests, along with 4 modern bathrooms to ensure everyone has plenty of space and convenience during their stay. Guests can enjoy a fully equipped large kitchen, an additional kitchenette for extra flexibility, and multiple indoor and outdoor areas perfect for socializing or unwinding.brbrStep outside to experience the property’s inviting outdoor spaces, including a peaceful front porch, a spacious back patio deck ideal for dining and relaxation, beautifully manicured gardens, and exceptional privacy throughout the estate.brbrFor entertainment lovers, the home offers an incredible movie theater room complete with a massive 100-inch QLED TV and immersive surround sound system, creating the ultimate cinematic experience right at home. The main living room also features a large 75-inch TV for additional entertainment and gathering space.brbrOutdoor fun and activities are endless, making this property ideal for guests of all ages. Enjoy access to:brbr* Relaxing hot tubbr* Extra-large above-ground swimming pool (available from June - September)br* Basketball setupbr* Badminton setupbr* Volleyball areabr* Ping pong tablebr* Outdoor fireplace for cozy eveningsbr* Swings for family-friendly funbr* 75-inch TV in the living roombr* 100-inch QLED TV in the private movie theaterbrbrWhether you’re planning a relaxing escape, a family reunion, or a fun-filled weekend with friends, this property offers everything needed for a memorable and comfortable stay.brbrGUEST ACCESS brGuests will have access to nearly the entire property, including the full house, expansive landscaped gardens, and surrounding forest areas, allowing plenty of space to relax, explore, and enjoy the peaceful natural setting. Whether you’re spending time outdoors with family and friends, taking a quiet walk through the property, or simply enjoying the privacy and scenery, the grounds offer a truly relaxing retreat experience.brA few select areas may be restricted for maintenance or owner storage purposes and will be clearly marked or outlined in the check-in instructions provided prior to your arrival.brbrINTERACTION WITH GUESTSbrWe are committed to making your stay as comfortable and enjoyable as possible and will be readily available throughout your visit to assist with anything you may need. Guests are welcome to reach out to us anytime by phone or text with questions about the property, local recommendations, check-in assistance, or anything else that may help enhance your experience. We strive to provide quick and friendly communication to ensure you have a smooth, relaxing, and stress-free stay from arrival to departure.brbrOTHERbrPlease Note the Following House Guidelines:brbrGuests are not permitted to access the boiler room, as clearly indicated on the door signage.brbrAccess to the tree house is strictly prohibited for all guests at all times.brbrChildren must always be supervised while using the swings and outdoor play areas. Use of these amenities is at guests’ own risk.brbrIf the grill is used during your stay, we kindly ask that it be properly cleaned after each use.brbrTo help conserve energy and maintain the property, please ensure that all interior and exterior lights are turned off prior to departure.brbrFor safety and cleanliness purposes, garbage should never be left outside the home or on the property at any time.brbrWe appreciate your cooperation and respect for these guidelines, as they help us maintain a safe, clean, and enjoyable environment for all guests.

Luxury Windham Villa | 6BR, 4 BA, XL Pool, Hot Tub & Cinema, Gardens

Windham, New York, United States

Bed

Bath

Sleeps

$808.46

The Blue House is a beautiful large home nestled in the gem of the Catskills, Windham - just 5 minutes to restaurants and attractions on Main Street and 7 minutes to Windham Ski Resort. The perfect home for families or groups who to love ski, hike, relax and entertain. From kids to adults, there is room to enjoy the large living room, game/playroom with pool table, and large wrap-around deck equipped with an outdoor grill and hot tub.brbrNestled on 7 private acres with bridle paths joined to hiking trails, there is ample opportunity to appreciate the landscape without ever leaving the property - snowshoeing, cross-country skiing, mountain biking, hiking and exploring. When in season, forage for wild chanterelles, porcini, ramps, and blackberries. brbrRelax your muscles in the hot tub that overlooks a lake with a view of the mountains. By night, gaze up to see the stars put on a show. (tip: download a star tracker app to name the constellations)brbr$2500 refundable security deposit. $250/month for housekeeping.

Bucolic privacy with Hot Tub in Windham

Windham, New York, United States

Bed

Bath

10

Sleeps

$531.66

→ Hot tub, fire pit & indoor fireplacebr→ Mountain views, pond + private roadbr→ 1st-level bedroom with ensuitebr→ Dome Hockey Table; dozens of board gamesbr→ Fast WiFi + 2 Smart TVsbr→ 5min to Windham Mountain Clubbrbr→ Dog-friendly (pet fee applies). Sorry, no cats allowed.brbrAdd us to your favorites list for future stays!brbrThe spacebrbrWarm, welcoming, and made for mountain living. Brook Hollow sits on 1.4 private acres in the heart of the Catskill Mountains, just minutes from Windham Mountain Club. Whether you're here for the slopes in winter or the trails in summer, this 4-bedroom retreat has everything you need — a bubbling hot tub, crackling indoor fireplace, backyard pond, fire pit, and enough space for the whole group to spread out and feel at home.brbrbrOUTSIDEbrbrbr• Private hot tub with regular professional maintenancebr• Fire pit for evening gatheringsbr• Backyard pond w/ Adirondack chairsbr• 1.4 acres of natural surroundingsbr• Outdoor dining areabr • Sun loungersbr• Propane grill and all grill toolsbr• Outdoor games brbr✦ ✦ ✦ FIRST FLOOR ✦ ✦ ✦brbrBEDROOM 1 (w/ ENSUITE)brbr• King-size bed with cotton linensbr• TV with Apple TV for streamingbr• Several closetsbr• Reading chair with nature viewsbr• A/C + Ceiling fanbrbrFULL BATHROOM 1 (ENSUITE)brbr• Large, custom tiled showerbr• Large vanity and mirrorbr• Hair dryerbr• Ceiling fanbrbr✦ ✦ ✦ SECOND FLOOR ✦ ✦ ✦brbrBEDROOM 2brbr• Queen-size bed with cotton linensbr• Murphy bedbr• Ceiling fanbr• Wardrobe storagebr• Pond ViewsbrbrBEDROOM 3brbr• Queen-size bed with cotton linensbr• Murphy bedbr• Ceiling fanbr• Nature viewsbrbrBEDROOM 4brbr• Two (2) twin beds with cotton linensbr• Ceiling fanbr• DresserbrbrFULL BATHROOM 2brbr• Full bathtub and showerbr• Vanity and storagebr• Large mirrorbrbr✦ ✦ ✦ COMMON AREAS ✦ ✦ ✦brbrKITCHEN / DININGbrbr• Fully stocked, open kitchenbr• Pots, pans, baking and serving dishesbr• Full-size refrigerator and freezerbr• Toaster, teapot, microwavebr• Slow cooker; air fryer; blenderbr• Dishwasherbr• Keurig coffee maker, coffee pods and all essentialsbr• Dinnerware and glassware aplentybr• Salt, pepper, sugar, olive oil, select spicesbrbrLIVING ROOMbrbr• Indoor wood-burning fireplacebr• Large comfy couches for the whole groupbr• Smart TV (Roku) with streaming appsbr• Bluetooth speakerbr• Board games, books and reading materialsbrbrUPSTAIRS HALLWAYbrbr• Dome hockey tablebrbr✦ ✦ ✦brbrLAUNDRYbrbr• Washer and dryer on 2nd floor in bedroom 4br• Iron and ironing board availablebrbrbrPARKINGbrbr• Free parking on propertybr• Direct access to main entrancebrbrHEATING / COOLINGbrbr• Central heating and AC split units throughoutbr• Comfortable year-round!brbrTVbrbr• Two (2) Smart TVsbr• Living room (Roku) + primary bedroom (Apple TV)brbrNote: Fire extinguisher located on 2nd floorbrbrWe take cleaning very seriously and follow enhanced guidelines.brbrBrook Hollow is proudly managed by Canopy Collective, a premier co-hosting company.

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC

Windham, New York, United States

Bed

Bath

Sleeps

$863.44

Relax in this beautiful natural setting course that Windham has to offer, while at the same time enjoying all comforts of home with stunning views of the mountains and Surrounded by the Golf coursebrYes! The house is located in the unique location in the middle of the Golf course and with the ski slopes view. Just minutes from downtown Windham, you’ll be in proximity to all the best of the Catskills: Golf, ski, biking, water park, waterfalls, hiking trails lakes, dining, and winery

River & Golf Mountain Retreat

Windham, New York, United States

Bed

Bath

Sleeps

$683.72

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 slopes and summer activities like hiking and ziplining! Need more outdoor adventure Take a day trip to tour nearby sites like Howe Cavern or the Home of Franklin D. Roosevelt National Historic Site!brbr-- THE PROPERTY --brbrDeck + Fire Pit | Free WiFi | 1,800 Sq FtbrbrAn ideal mountain home base for exploring the Catskills, this Windham rental boasts modern touches, a bright living room, and a deck that invites you to spend time outdoors. brbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Full Bed, Twin Bed, Twin Trundle BedbrbrOUTDOOR LIVING: Deck, patio table, chaises, gas grill, fire pit, Adirondack chairs, spacious yard, cornholebrINDOOR LIVING: 2 Smart TVs, gas fireplace, hardwood floors, large windows, clawfoot tub, dining tablebrKITCHEN: Fully equipped, dishwasher, drip coffee maker, stainless steel appliances, wine coolerbrGENERAL: Air conditioning, central heat, washer/dryer, linens/towels, suitable for children, suitable for elderly brPARKING: Driveway (6 vehicles)brbr-- THE LOCATION --brbrOUTDOOR RECREATION: The Windham Path (1.9 miles), Windham Mountain (3.0 miles), Hunter Mountain (10.5 miles), Kaaterskill Falls Trail Head (15.7 miles), Kaaterskill Wild Forest (17.0 miles), North/South Lake (17.2 miles), Dutchman’s Landing Park (26.5 miles), Kaaterskill Clove (27.2 miles), Howe Cavern (40.4 miles)brATTRACTIONS: Five State Lookout (8.0 miles), Mountain Top Arboretum (11.0 miles), Zoom Flume Water Park (12.5 miles), Tannersville (14.5 miles), Village of Catskill (25.8 miles), Hudson (29.8 miles), Home of Franklin D. Roosevelt National Historic Site (61.1 miles)brDINING: Chalet Fondue (1.6 miles), Ze Windham Wine Bar (2.3 miles), Millrock Restaurant (2.3 miles), Vesuvio (2.8 miles), Zack’s Place (2.8 miles), Chicken Run (3.3 miles)brAIRPORT: Albany International Airport (63.4 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- Absolutely NO pets allowedbr- The maximum occupancy is 8. Absolutely no more than 8 guests are allowed at the propertybr- No events, parties or large gatherings br- Additional fees and taxes may applybr- Photo ID may be required at check-inbr- NOTE: Your safety matters. This property features 2 exterior security cameras, above the front door and back deck, all facing outward. They do not look into interior spaces

Luxury Home w/ Deck: Explore the Catskill Mtns!

Windham, New York, United States

Bed

Bath

Sleeps

$723.08

Newly Listed!! Beautiful mountain home located on a quite private road. This is a large 5 bedroom home only a few minutes from downtown Windham/Ski Resort and 20 minutes from Hunter Ski Resort. This property has massive lush green yards, amazing outdoor seating space, Weber BBQ Grill, superfast internet, and 5 minutes from downtown Windham. This property was recently renovated and fitted with all brand new appliances and furniture to provide utmost comfort for our guests.

(New Listing) Beautiful mountain home on private road

Windham, New York, United States

Bed

3

Bath

14

Sleeps

$1334.57

This 6 Bedroom, 4 bath chalet is ski in/ski out and directly on the Windham mountainside just a short walk from the base of Windham. It is a modern built timber frame home with all of the amenities a family would need to live and work in the fresh mountain air. Go for a hike to the top of Windham mountain, go fishing or tubing down the river or explore the Hudson River Valley while sleeping in luxurious linens, cooking in a fully stocked kitchen and entertaining at the ample copper bar. brbrThe basement which offers radiant heat throughout has a 6 person bunk room, a large bedroom with 2 x twins, a full bath, and an entertainment room for kids or teens. The boot room opens directly onto the mountain and provides plenty storage space and an extra place for sitting, eating or dressing . brbrThe 1st floor offers a king bed guest suite that looks right out of Switzerland. There is a queen bedroom across the hall from a full bathroom. Radiant heat provides cozy comfort in all bathrooms throughout the house. The 1st floor open floor plan is perfect for entertaining as the large kitchen looks over a 12 person table, a large copper bar and living room. This open floor plan has a porch that overlooks farmland and mountain ranges for as far as the eye can see. It is perfectly appointed to appreciate the morning light in the kitchen and the sunset on the deck in the afternoon. brbrThe top floor is a master suite with a gorgeous marble bathroom including a separate shower and claw foot tub. A small nursery now with twin platform beds offers extra sleeping space for stowaways and a loft type common area overlooks the same beautiful countryside of the Catskill Mountains. brbrThe house is surrounded by woods and waterfalls where wild turkeys roam and kids can explore. There is plenty of private parking on the property and the front lawn is a ski mountain where you can roam free for hours upon hours. Listen to a book and hike to the top or bring your bicycle and enjoy the biking trails that Windham Mountain has to offer.

New Custom Built Catskill Mountain Chalet with Elevator

Windham, New York, United States

Bed

Bath

Sleeps

$922.13

Breathtaking Design, Newly Constructed Farmhouse with Wooded Views in Windham NY ** Special Culinary Promotion! **Book your stay of 3 or more nights and enjoy a private gourmet dinner served in our luxury on-property barn for a discounted fee of $100 per adult (over 16) guest. BYOB, mixers provided. For children under 16 we'll provide complimentary burgers, hot dogs and sides. Book your May stay of 3 or more nights now to receive this special culinary promotion!Farmhouse is brand-new construction! Modern design offers the perfect blend of beauty and peace of the mountains, and the luxurious comforts of home. Home features 4 bedrooms: 2 with king beds and 2 with two twin beds each that can be combined to form 2 additional kings. Each bedroom has full ensuite bathrooms with large showers. Brand-new high-end appliances, fully-equipped kitchen, washer/dryer, Pella windows. Enjoy the convenience of radiant floor heating and WiFi. Large living room with vaulted ceilings and fireplace provides the perfect spot for family and friends to relax in comfort. Sliding doors lead to private patio area. On-premises private hiking trails and pond. Convenient to Ski Windham, golf, restaurants and local attractions. No pets please. Enjoy all-season beauty and comfort with your family and friends in your private luxury mountain retreat. We now have 2 new-build additional houses on the same circle [#37 and #39 Knollwood Circle]. Please contact the host for information on renting 1, 2 or 3 houses for a larger family / reunion / business meeting!Inquire about mid-week (Tues, Wed, Thurs) pricing specials; and pricing specials on stays of 7 days or longer!

Ask about Spring Specials!

Windham, New York, United States

Bed

Bath

Sleeps

$490.06

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. Year-round activities include exploring the hiking trails of the Catskill Mountain area, sampling local wineries & breweries, and soaring down the slopes of Windham Mountain or Hunter Mountainbrbr-- THE PROPERTY --brbr2,160 Sq Ft | 1 Mi to Windham Mountain | Lush Forest & Mountain ViewsbrbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Twin Bunk Bed, Queen Bed | Bedroom 4: Queen BedbrbrOUTDOOR LIVING: Private hot tub, spacious deck w/ mountain views, 6-person dining table w/ pergola, fire pit, large backyard, gas grill (propane provided)brKITCHEN: Fully equipped, fully renovated, stainless steel appliances, drip coffee maker, dining table, wine fridge/wet bar, granite countertopsbrINDOOR LIVING: 1 Smart TV, wood-burning fireplace, convertible dining/pool table, vaulted ceilings, exposed-beam woodwork, laptop work stationbrGENERAL: Linens/towels, 2 split-unit air conditioning systems (1 to cool the downstairs & 1 in the master bedroom), washer/dryer, trash bags, paper towelsbrACCESSIBILITY: 2-story home, stairs required to enterbrPARKING: Driveway (5 vehicles)brbr-- THE LOCATION --brbrOUTDOOR ATTRACTIONS: Windham Bike Park (1.2 miles), The Windham Path (2.4 miles), Elm Ridge Wild Forest (4.5 miles), Windham High Peak (6.2 miles), Windham-Blackhead Range Wilderness (13.1 miles), Kaaterskill Wild Forest (17.5 miles), Westkill Mountain Trailhead (21.2 miles)brWINTER ACTIVITIES: Windham Mountain (1.2 miles), Hunter Mountain Resort (11.1 miles), Plattekill Mountain (29.1 miles), Belleayre Mountain Ski Center (28.9 miles)brDINE & DRINK: Catskill Mountain Country Store - Windham (0.2 miles), The Windham Local (0.6 miles), Millrock Restaurant (0.6 miles), Bistro Brie & Bordeaux (0.6 miles), Chicken Run (0.7 miles), Ze Windham Wine Bar (0.7 miles)brDAY TRIPS: Albany (52.1 miles), Historic Site of the 1969 Woodstock Festival (72.5 miles), Saratoga Springs (76.0 miles), Catskills (boating, sailing, etc)brAIRPORT: Albany International Airport (50.8 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- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This 2-story home requires stairs to enter

'The Mountain House:' Windham Retreat w/ Hot Tub!

Windham, New York, United States

4

Bed

Bath

8

Sleeps

$477.53

Your Windham adventure begins at this fabulous 4-bedroom house. Inside, guests find a welcoming space featuring one king bed and three queen beds, perfect for families or groups. Two bathrooms include a relaxing bathtub and handy hair dryer for added comfort. The house stays cozy with heating and cool with AC, making it a great retreat any time of year. Whether you’re unwinding after a day of exploring or gathering for a meal, this gorgeous home offers a perfect blend of comfort and style. Our place is equipped for both long or short stays to make your holiday one to remember.

Spacious 4-bedroom house in tranquil Windham with AC big deck and fire pit BBQ

Windham, New York, United States

4

Bed

1

Bath

8

Sleeps

$531.43

Escape to this stylish mountain retreat, situated on 3 private acres with breathtaking views of Windham + Hunter Mountains. Relax in the hot tub, cozy up by the wood-burning fireplace, or unwind with a game in the new rec room. With space for large groups, 2 kitchens, and year-round access to the best of the Catskills, it’s the ultimate getaway for adventure and relaxation.brbr*Amazing views of the landscapebr*Laundry br*EV chargerbr*Pingpong + foosballbr*2 min drive to townbr*5 min drive to Windham MtbrbrGet cozy by the wood-burning stove in the great room that features high ceilings and a very comfortable layout. Almost every seat in the living/dining room has a beautiful view of the mountains. The home is the perfect getaway for all seasons. There is so much to do in the Catskills including Windham Mountain for skiing and in the summer mountain biking, Elm Ridge hiking trail, Kaaterskill Falls, Zoom Flume Water Park, West Kill Brewery, Bearpen Mountain, and there are also the towns of Hudson, Catskill, Phoenicia, Tannersville, Coxsackie, Woodstock and of course the idyllic village of Windham with many things to check out. brbrBeds & Baths Overview br*5 bedrooms, 3 bathroomsbr*3 bedrooms located on the main level, 2 on the lower levelbr*Linens and essentials are providedbrbrMain Levelbr*Cozy open-concept living/dining spacebr*Wam ambiance and wood-burning stovebr*Huge couch with views of the mountain br*HDTV w/ streaming services, cable, fast wifibr*High Top dining table and bar seatingbr*Table can double as a dedicated workspace if neededbr*Fully equipped kitchen featuring major appliances, soda stream, blenderbr*Master bedroom with a queen bed and ensuite bathroombr*Second bedroom with queen bed, desk, and deck accessbr*Third bedroom has 2 bunk bedsbr*Additional full bathroom brbrLower Levelbr*Game room with foosball and ping pong tablebr*Wood stove, TV, and lounge areabr*More stunning views from this spacebr*Second, fully functioning kitchen br*Fourth bedroom with a queen bedbr*Fifth bedroom with a bunk bed and a twin daybedbr*Full bathroombrbrOutdoor Amenitiesbr*Large deck with chiminea and conversation seatingbr*Weber’s grill and pizza ovenbr*Relaxing hot tubbr*Outdoor seating and diningbr*Fire pit on the lawn with seatingbr*Spot ski trails and Hunter Mountain from the front yardbrbrAfter a day of skiing, hiking, and exploring, unwind in complete privacy at the property. Check out more of the property on IG windhamskyybrbrbrFor a video walkthrough please search on YouTube: `Windham Skyy.`brbrGuests will have access to the entire home. There is parking at the property in the driveway for at least 6 cars, as well as a space inside the garage. brbrEasily check in with the smart lock and garage code provided before arrival.brbrbrWhen you are using the hot tub please utilize the cover lifter to fold in half and then flip the lifter up to hold cover. It is very important that the cover lifter be utilized and the cover to not be left on the ground. Please do not use any glassware in the tub. If you bring a beverage with you please dispose in the garbage when you are done.brbrFeel free to reach out through the Airbnb app if you have any questions or need assistance. We’re happy to help and will respond as quickly as possible.brbrThe home is nestled in Windham on a quiet, private road just parallel to Route 23. Secluded and peaceful, yet incredibly convenient—it`s only a 2-minute drive to the center of town and 5 minutes to Windham Mountain. Enjoy the perfect balance of privacy and easy access to everything Windham has to offer, including smaller grocery stores, a pharmacy, gas stations, and more! brbrThings to Do in the Catskillsbr*Windham Mountain: Skiing in winter, mountain biking in summerbr*Elm Ridge Trail: Hikingbr*Kaaterskill Falls: Scenic waterfall hikesbr*Zoom Flume Water Park: Family-friendly funbr*West Kill Brewery & Bearpen Mountain: Local brews and outdoor adventuresbr*Explore charming towns like Hudson, Catskill, Phoenicia, Tannersville, Coxsackie, Woodstock, and the idyllic village of Windham with shops, restaurants, and attractions.brbrElm Ridge - 2 minute drivebrPhoenicia - 30 minute drivebrCoxsackie - 40 minute drivebrHudson - 35 minute drivebrCatskill - 29 minute drivebrTannersville - 23 minute drivebrWoodstock - 50 minute drivebrbrHaving a vehicle is key for exploring the region and all it has to offer. Parking is available on the property for up to 6 cars in the driveway and room for 1 more car in the garage.brbrThis two-level home offers flexible and spacious accommodations. The lower level is accessible via spiral stairs or a private entrance and features an additional kitchen and bathroom. The main level includes three bedrooms and sleeps up to eight guests, while the lower level comfortably sleeps six. Perfect for larger groups or families seeking extra space and privacy.brbrA $100 fee applies for guests bringing dogs.brbrPlease have a look at our house rules before booking.brDisclaimer of LiabilitybrBy booking and staying at this property, guests acknowledge the inherent risks and accept full responsibility for their safety and well-being during their stay.brbrGuestsbrThe maximum occupancy is 8 guests. All overnight guests must be registered with the host prior to arrival. Guests are responsible for the actions of any visitors or invitees during their stay.brbrCheck-In and Check-OutbrCheck-in is available anytime after 4:00 PM.brCheck-out is required by 10:00 AM on departure day.brbrNoise and Quiet HoursbrGuests must keep noise to a minimum, especially during quiet hours from 10:00 PM to 7:00 AM, to respect neighbors and comply with local noise regulations. Failure to address noise violations promptly may result in eviction without a refund.brbrEvents and PartiesbrParties, events, or large gatherings are strictly prohibited. Violations will result in immediate eviction, additional cleaning charges, and notification to the booking platform. Confetti, glitter, and excessive trash are also prohibited, and any violations will incur an additional $250 cleaning fee. We kindly ask that you help us maintain a peaceful environment for all guests and neighbors.brbrPetsbrDogs are welcome with an additional $100 fee, which must be paid prior to arrival. Dogs must be well-trained and carefully supervised at all times. To prevent excessive mess, damage, or shedding, pets should not be left unattended and are not allowed on the furniture. An additional cleaning fee of $250 will apply if excessive pet-related mess or damage is found. brbrWeapons PolicybrWeapons, including firearms, are strictly prohibited on the property. If a weapon is brought onto the property, the booking may be immediately canceled without a refund. Any weapons left behind will be reported to authorities.brbrSmoking and VapingbrSmoking or vaping of any kind, including marijuana, is prohibited inside the house or anywhere on the property. Violations will result in the immediate cancellation of the booking without a refund and a $1,000 cleaning fee. brbrCandlesbrThe use of candles is strictly prohibited.brbrSecurity Cameras and Safety DevicesbrOutdoor security cameras are located above the garage. Tampering with security cameras and smoke detectors will result in immediate termination of the booking without a refund.brbrToilet UsagebrOnly toilet paper should be flushed. Feminine hygiene products, wipes, paper towels, or any other items must not be flushed, as they may clog the plumbing. Guests may be charged up to $1,000 for damages caused by improper flushing.brbrChild SafetybrChildren must be supervised at all times. The property is not baby-proofed, and guests are fully responsible for their children’s safety.brbrLitteringbrLittering is strictly prohibited, including leaving food or trash around the property. Additional cleaning fees of $250 will be charged for violations.brbrHot TubbrGuests must follow these instructions when using the hot tub. If it is found that the guidelines were not followed, an additional fee of $250 will apply. When using the hot tub, please use the cover lifter to fold the cover in half and lift it securely onto the holder. It’s important to avoid placing the cover on the ground. For safety, do not bring glassware into the hot tub. If you bring a beverage, kindly dispose of any trash in the bin when finished.brbrBBQ Grill RulesbrThe BBQ grill must be used only in the designated area on a stable surface, away from flammable materials. Always supervise the grill during use and have a fire extinguisher nearby. Do not use accelerants, and allow the grill to cool completely before cleaning. Thoroughly clean the grill, including grates and grease trays, after each use.brbrOutdoor Fire Pit/ChimineabrAlways supervise the fire pit/chiminea and keep children and pets at a safe distance. Use only dry, seasoned wood, and avoid accelerants or burning toxic materials. Fully extinguish the fire before leaving the area, ensuring all embers are out.brbrDeparture TasksbrBefore leaving, please complete the following tasks:brbr1) Gather used towelsbr2) Turn things offbr3) Throw out trashbrbrDamages, Breakages, and FurniturebrTreat the property and its contents with care. Only use appliances for their intended purposes. Report any damages to the host immediately.brbrPersonal Belongings and ValuablesbrThe host is not responsible for any loss of money, jewelry, or other valuables. Ensure personal items are secure during your stay and collect all belongings before departure.

Idyllic Mountain Stay Hot Tub, Wood Stove, Games

Windham, New York, United States

Bed

Bath

Sleeps

$3371.14

Luxurious ski in/ ski out, three-story chalet located directly on the slopes of Windham Mountain and minutes drive from the town center. Perfect for one or two families seeking a private and luxurious getaway and keen skiers wanting to maximize their ski time. For explorers of the Catskills, Hunter Mountain Resort is a 10 mile trip and Hudson is just 30 miles east. Over 5,000+ sf slope side luxury and warmth. The chalet is a spacious and beautifully-appointed home, comfortably sleeping and dining 10+ guests. It has 7 bedrooms, all of which are ensuites, over the three floors. There is also an amazing den (TV, bar, pool table, Pac-Man), a chefs kitchen, ski room and a large living room that also opens up to a rear yard and outdoor entertaining space with fire pit. Perfect for apres-ski with friends! Other amenities include a games table and cozy snug TV-watching space, exercise area including The Mirror, outdoor fire pit and house and garden-wide sound system. A tree house for junior skiers in the back yard! This house is a ‘Smart Home’ wired for comfort allowing control of, lights, heating, security, audio and video through Savant remotes.brbr* 7 night minimum stay. br** Seasonal/Monthly rentals available. Rates upon request.

Luxurious ski in/out, 3-story chalet directly on the slopes of Windham Mountain

Windham, New York, United States

Bed

Bath

Sleeps

$416.13

Wake up to mountain views & end your day under the stars in your private hot tub-a perfect Windham escape! This 3BR, 2BA townhome is steps from Windham Mountain Club, ideal for skiers, hikers, bikers, and fall foliage seekers. Cozy up by the fireplace, sip morning coffee on the deck, & enjoy full access to a heated indoor community pool. Family & pet friendly (w/ fee). Whether you're chasing snowflakes or sunshine, your Catskills getaway starts here!brbrThe spacebrbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 king bedbr- Bedroom 3: 1 twin bunk bedbr- Additional Sleeping: 1 portable cribbrbrCOMMUNITY AMENITIESbr- Indoor pool & hot tubbr- Tennis courtsbr- Ski resort (w/ additional fees, paid on-site)brbrCommunity Pool Closure Notice - April 2026:brThe community indoor pool is currently closed for maintenance and is expected to reopen by Memorial Day weekend. Availability of shared amenities is subject to the homeowners association and cannot be guaranteed.brbrINDOOR LIVINGbr- Flat-screen TV w/ Fire TV Stickbr- Wood-burning fireplace (bring your own wood)br- En-suite bathroomsbrbrOUTDOOR LIVINGbr- Private hot tubbr- Deck w/ seating & dining areabrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Keurig coffee maker (coffee provided), toasterbr- Cooking basics, dishware & flatwarebr- Ice maker, trash bags/paper towelsbr- Dining table, high chairbrbrGENERALbr- Central heatingbr- Wall A/C unit (Bedroom 2), window A/C unitsbr- Washer/dryer, laundry detergent, iron/boardbr- Linens/towels, complimentary toiletries, hair dryerbr- Free WiFibrbrFAQbr- Grill not available for guest usebr- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- 2-story townhome, 2 exterior steps required to enterbr- Bedroom & full bathroom on 1st floorbrbrPARKINGbr- 2 Parking spots labeled #93 (2 vehicles)br- Free street parking (first-come, first-served)brGuest accessbrGuests staying 11 nights or more will have access to the community clubhouse, including the fitness center and game room.brbrAll guests can enjoy the indoor pool, hot tub, tennis courts, and easy access to the ski resort. There are 2 key fobs on the console near the kitchen that can be used for entry into the indoor pool. Please do not lose these fobs - $150 fee to replace them.brbrOther things to notebr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes). If a pet is observed without the fee payment, this is subject to cancellation of reservation mid stay.br- No events, parties, or large gatheringsbrbr- This 2-story townhome requires 2 exterior steps to enter; the 1st floor includes a bedroom and full bathroombrbr- Access to the community clubhouse (including the fitness center and game room) is only available for guests staying 11 days or longer. All guests can access the indoor pool, hot tub, tennis courts, and ski resort. There are 2 key fobs on the console near the kitchen that can be used for entry into the indoor pool. Please do not lose these fobs - $150 fee to replace them.brbr- Convenient location near outdoor recreationbr- Walk to Windham Mountain Clubbr- 3 miles to The Windham Path & 5 miles to Elm Ridge Wild Forestbr- 10 miles to Zoom Flume Water Park & 11 miles to Mountain Top Arboretumbr- 17 miles to Kaaterskill Wild Forest: trails, waterfallbr- 64 miles to Albany International Airport

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham, New York, United States

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Sleeps

$965.52

Located at the West end of Main Street. Guest get all the convenience of being in the Town of Windham while having complete privacy. Home has large porch and living area with bird's eye view of the ski mountain which is directly across the valley. After a day of skiing sit in your private hot tub and enjoy the views of the slope. Get ready to relax in this 5-bedroom house in Windham. The space features a king bed, three queen beds, and a full bed, plus an additional loft space with twin beds for extra comfort. With three full bathrooms, guests find convenience at every turn. The home has a custom built fireplace located in the living area with a complimentary supply of firewood. The house stays cool and comfortable with air conditioning and heating throughout. Whether you’re working or unwinding, the serene atmosphere makes it easy to feel at home. Enjoy all that Windham has to offer when you stay at our place.

Spacious 5-bedroom house in delightful Windham with Stunning View of Ski Area

Windham, New York, United States

Bed

Bath

Sleeps

$386.1

Beautiful Country Setting 3 min to Windham town center w Large deck/ New Hot Tub and Large Wood Fire pit across our bridge next to a wonderful Stream w 6 cedar Adirondack chairs surrounding our fire pit. A serene setting of 6 chairs on a new bluestone patio stream side, for morning coffee or evening drinks listening and watching the running water closeup.brEnjoy one of our newest amenities , a fun game of bocce just next to our fire pit,bean bag toss. br Ultra Modern spacious kitchen with a Barista Breville Espresso Cappuccino machine with built in grinder, comfortable living room with flat screen TV , DVD , WiFi , DIRECTV, HBO ,charming pellet stove,1906 antique player piano. 2 person shower for relaxation after a hike or skiing. Large deck, with barbecue and outdoor flat screen tv 50” on deck, with a gas fire pit in front of couch on deck, with stream behind house. . A assortment of board games , horse shoes. Wake up to deer in the backyard or walk across the street to see the beautiful horses or sheep. A short drive to a beautiful walking , or cross country skiing path with beautiful views. Great location for Hiking or a relaxing day on the golf course. Zip lining 15 minutes away, or relax and take in a movie at the local 3 screen theatre right in town. Zoom Flume water park a 8 min drive. brbrA short drive to Main st in town 2.1 miles and 3.4 miles to Ski Windham, and Hunter Mtn Ski area 15 min drive .brbrA 12 min drive to CD lane park that has beachfront on a lake. Also a 25 min drive to North Lake and South Lake that are beautiful large lakes for lying on the beach, or renting a kayak or bring your own. Also some breathtaking views at the beautiful 5 state view at the Historic site of the Catskill Mountain House and Boulder Rock, and visit the Kaaterskill water fall overlook or take a beautiful hike up from the bottom of the falls to inspiration point . Also we have a wide selection of excellent restaurants in town and in the area. A short 40 min drive will bring you to the beautiful Historic town of Hudson. The town has many fine restaurants and tremendous character along with many interesting antique shops and more. The property has outdoor security cameras facing the front driveway and bridge and streamside patio for security and insurance purposes.

Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub

Windham, New York, United States

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Bath

Sleeps

$195.42

Make your next trip to the Catskills one to remember when you stay at this 2-bedroom, 2-bath vacation rental! Located on the 2nd floor and surrounded by the forest, this house offers fantastic views of the mountains from the expansive decks. Though you’ll feel tucked away from it all during your stay, you’ll only be a few minutes from downtown Windham and the Windham Mountain Resort for year-round activities. Return from a day of outdoor adventures and gather with friends by the fire pit!brbr-- THE PROPERTY --brbrOutdoor Dining Area | Free WiFi | Off-Street Parking | Hiking NearbybrbrSpring, summer, fall, or winter, this vacation rental is the perfect home base for families and groups of friends seeking a unique outdoor retreat in the Catskill Mountains. brbrBedroom 1: Queen Bed | Bedroom 2 (Bunk Room): Twin/Full Bunk Bed | Den: Queen Sleeper Sofa brbrINDOOR LIVING: Flat-screen TV, skylights, 2 electric fireplaces, en-suite bathroom, games, Free Wifi, cablebrKITCHEN: Fully equipped, Keurig coffeemaker, coffee provided, cooking essentials, breakfast bar, pub table for 8 brOUTDOOR LIVING: Gas fire pit, outdoor dining table, patio, patio furniture, forest and mountain views, side yard, gas grillbrGENERAL: 1,200 Sq Ft, washer/dryer, linens/towels, ceiling fans, central heating/AC, complimentary toiletries, trash bags, paper towels brPARKING: Driveway (3 vehicles)brbr*NOTE: A long-term renter lives on-site in a separate 1st-floor unit and may be present during your stay*brbr-- THE LOCATION --brbrOUTDOOR RECREATION: Windham Path (1 mile), Escarpment Trailhead (2 miles), Windham Mountain Resort (3 miles), Hunter Mountain Resort (10 miles), Kaaterskill Falls and North/South Lake (16 miles), Platte Clove Preserve (18 miles)brSUMMER ACTIVITIES: Windham Mountain Bike Park (3 miles), New York Zipline Adventures LLC (10 miles), Zoom Flume Water Park (10 miles), Colonial Country Club (13 miles), Thunderhart Golf Course (16 miles), Bailiwick Animal Park and Riding Stables (21 miles)brATTRACTIONS: Five State Lookout (6 miles), Thomas Cole National Historic Site (23 miles), Olana State Historic Site (26 miles), Howe Caverns (40 miles)brDAY TRIPS: Tannersville (13 miles), Village of Catskill (23 miles), Hudson (28 miles), Woodstock (30 miles)brAIRPORT: Albany International Airport (61 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- No pets allowedbr- Quiet hours 11 pm to 8 ambr- No events, parties or large gatheringsbr- *NOTE: A long-term renter lives on-site in a separate 1st-floor unit and may be present during your stay*br- Please note the property is located on the 2nd floor and may not be suitable for elderly guests br- Additional fees and taxes may applybr- Photo ID may be required upon check-in

Catskills Home, 5 Mins to Windham Mtn Resort!

Windham, New York, United States

Bed

Bath

6

Sleeps

$1188.0

MINT 5BR, 4.5BA, brand new home. Full modern furnishing complete 5/1. Panoramic views from 5 acre hilltop with forest backdrop & rushing seasonal stream. Great room w/16-ft vaulted ceiling, exposed beams, 2-sided fireplace. 8-ft glass doors open to elevated covered porch w/outdoor seating and comfort stove. Primary suite and second en suite located on the main floor. brLower level: Third en suite, fourth bedroom and bunkroom, entertainment/TV space, wet bar; sliding glass doors open to patio.

Brand NEW MINT Windham 5BR/4.5BA home on 5 acre, wooded hilltop.

Windham, New York, United States

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