Vacation Rentals By Owner In Windham, NY

$479.25

Windham Immaculate Ski Chalet w/ Secluded Fire Pit Available 25/26 Ski Season!

Windham, New York, United States

Available for Season 25/26 Ski Season! $15,000. Nov 15, 2025 - April 15, 2026brThis home is a super immaculate, upscale, classic ski chalet nestled on 1 private wooded acre. Home features 3 bedrooms and 2 full baths and comfortably sleeps 4 adults and 4 children. Den with wood burning stove & 2 bedrooms downstairs, complete with new down comforters. 1 bedroom with a queen size bed, 1 with 2 bunk beds, sleeps 4, & a full bath downstairs. Master bedroom is upstairs, with area that would be great for a crib. It has cathedral ceilings, large windows, fire place with mountain views in winter. Posh hotel towels, new down comforters, walk in closet & a master bath attached. There are 2 entrances. Main entrance takes you upstairs to living room. Entrance on the ground level opens to a mud room for ski equipment & coats. There is also a laundry area with a brand new washer and dryer. This leads to a family room with has a surround sound system with DVD and TV with cable service & Internet accessbrbrbrAmenities: New Carpeting just installed throughout house!!! Upstairs is a beautiful open floor plan, with high cathedral ceilings & modern ceiling fan, large windows. The living room has a gorgeous floor to ceiling stone fireplace. Stainless steel dining table in dining room. The kitchen has new super clean new appliances & is fully furnished with all the tools needed to entertain. There are beautiful mountain views in the winter, from these living room windows. There is also a blue ray DVD in the living room as well as a new flat screen LCD TV with cable service included, Wireless internet service included. Glass sliding doors to wrap around deck with seating for 8 patio set, Weber gas grill, & natural ultra private setting. brMaster bedroom & bathroom located on same floor as living room.brbrThe house is located approximately two miles from town & ski Windham, boasting 2 beautiful golf courses, and many excellent restaurants.brbrSpring, Summer & Fall activities include mountain biking, horseback riding, swimming, tubing, canoeing, fishing, and hiking trails. Summer and Fall cultural festivals, concerts, art galleries, antiques, fall foliage displays, apple picking and fine theater round out the season activities in Windham, or just sit on the deck and relax! Winter activities include skiing, snowboarding & snowmobiling at area facilities. The house is super ski chalet cozy & warm with a fireplace upstairs and a wood burning stove which warms the entire house through floor vents to living room upstairs.

Bed

Bath

Sleeps

$376.92

/ Nightly

Private Vacation Home

Windham/Hunter Mountain

Windham, New York, United States

Relax and enjoy our large home located on a private secluded block. Offering 4 master bedrooms with 3 full size bathroom jacuzzi hot tub both indoor and and out doors. Many amenities with separate entreating area located within less than 5 minutes away from Windham mountain and 10 minutes away from Hunter Mountain. Fully stocked kitchen, new appliances, all new bedding. Home sleeps 10 comfortably. Your access code will be the day of check-in for example 0710. This will be your personal access code to enter the home through the FRONT door and during your stay. The bottom lock should remain unlocked whenever leaving the home and especially at check out . In the event it’s locked please let us knowbrbr 4. At check in, please walk through the home to assure nothing is broken or out of place. Please notify us immediately if something is broken. (There are few small marks on the kitchen counter and your usual wear and tear)brbr 5. There are various signs around the house to help you navigate the lightingbrbr 6. The WiFi name is Aris34-B and the password is 2SY9AD601967.brbr 7. Due to severe allergies on most guests and family, we have a NO PET policy.. As stated in the the listing brbr 8. We kindly ask no shoes inside the home, there are designated areas inside and in the garage for shoes. br 9. DO NOT bring any indoor furniture, out. br 10. Smoking indoors is prohibited.br 11. Please be considerate of the neighbors with noise. Music can be played outdoors from 9:00 AM - 10:00 PM according to the town guidelinesbr 12. ****Garbage must be dumped at the local transfer station during and at the conclusion of your stay. Please dump garbage/recyclables at: Greene County Solid Waste RR 21, Windham, NY 12496 Must check with their schedule and time especially with holidays. We recommend take the garbage out daily on your way out it’s right up the block. Each bag costs $2 and recycling is free. (Windham country does not offer home services for garbage pick up. It is on the way out.)br 13. ****If trash is left behind, there will be a charge of $3 per bag plus what ever service fee our staff charges us garbage disposed of. (Please understand this is the fee the cleaning company will charge) br 14. ****Please be aware the bears are very active during this time of year, make sure garbage and food are kept away from doors and not left outside. br 15. Excess detail cleanings any garbage left behind and damages will result in charges and request of the security deposit.br 16. HOT TUB GUIDELINES as follows:brbra.) Please wipe feet anytime before entering the tubbrb.) NO food in the tubbrc.) Keep Cover closed at all times when tub is not in use.brd.) Please rinse off before entering the tub if you have lotions/creams on your skin.bre.) If you have had a lot to drink please avoid the hot tub.brf.) Anyone under the age of 18 should NOT be use the hot tub without parental consent.brg.) DO NOT play with the hot tub settings. It is programmed to on a specific schedule. Only use the jets and light options on the tub.brf) Make sure Jets are off after each use and cover the tub. brbr 17. WHOLE HOUSE HEATING/cooling Guidelines. brA) Each room has ceiling fans and each bedroom has ac units in them (please do not leave the ac or baseboard heat running all day when not home) brB.) Upstairs heat should only be used with the DIAL thermostat. This is for the central heat. brC.) ELECTRIC BASEBOARDS ARE FOR EMERGENCY USE ONLY.brD.) Down stairs heater, do NOT allow children near or around the heating element. The heater can be turned on simply by moving the dial slightly till it clicks on. brE.)Wall heaters in kitchen and in master bedroom are NOT allowed to be on for extended periods of time.brF.) Bathroom ceiling heaters MUST be turned off immediately after use of the bathroom. brG.) When leaving, please turn heaters to 55 degrees.brH.) MASTER BEDROOMS HEATING.-The electric baseboards are the main heating element in these rooms. To turn on each baseboard simply turn the dial on the end caps of the baseboards clock wise. To turn off it will be counter clock wise. Please make sure to turn off when not in use. And nothing is sitting on the base of the heat. brI.) there is no central air conditioning at the home. Open windows and the ceiling fans work great. brbr 18. FIREPLACE bra) Lever must be closed when the FP is not in use to avoid animals entering the home brb) Please refrain from using fireplace the morning of checkout. brc) When in use , turn the LEVER inside the top of the fireplace towards you. This opens the vents and allows the smoke to exit out the chimney and will not smoke the room. brd) Open a window when using the fireplace. br19. ALEXAS brAre NOT to be, removed from their designated location. br20. Each room is equipped with a smart TV loaded with Netflix and YouTube. br21) You may yourself to our propane BBQ grill. Located in the garage please take it outside and cook in the driveway. (Clean and close the nozzle once done put back in the garbage after use)

Bed

Bath

Sleeps

$1544.4

/ Nightly

Private Vacation Home

A'Neils Windham Ski Lodge & Family Retreat

Windham, New York, United States

This historical Inn is just minutes from the Windham Ski area, as well as 2 professional golf courses, a vineyard, numerous state hiking trails and much more. This beautiful estate has 9+ bedrooms, 10.5 baths, a home office, large family gathering space, a large dining area, rec. room and living areas. Just 2.5 hours from the metropolitan area makes this an easy weekend commute. Come and see everything this beautiful house has to offer!brThis West Windham House has a brand new wrap around porch with roof. As well as a gas and charcoal grill for your family to enjoy. There is a new stainless steel refrigerator, six burner professional stove, Verizon Fios Internet, pool table, wood burning fireplace & washer & dryer in the home as well.brSpacious covered front porch is complete with outdoor lighting, fan and plenty of seating, table and bar allow for comfortable outdoor gatherings, season to season. Providing an amazing view of the neighboring mountain tops.brMultiple top-quality restaurants to choose from, movie theatre, mini golf, seasonal snow tubing, ski/snowboard your choice of three local mountains (Windham, Hunter and Belleyre) cyclist, golfers, hikers, bird watchers, nature enthusiast, explorers, mountain folk, musicians and music lovers will be at peace on Windhams' top Lodge, A'Neils.

Bed

Bath

Sleeps

$248.4

/ Nightly

Cabin

Lake view Cabin on Lake Heloise

Windham, New York, United States

Charming cabin to stay and play in at the lake. Have fun swimming and fishing on the lake. This property was a campsites and cross-country ski business so there are hundreds of acres of lettered trails off the property for hiking. We have canoes and Kayaks to rent. Very peaceful.brbrThe ski mountain is 5 minutes away and you can see the slopes from our lake or from the back lawn.brbrPets are welcome pet fee is $30 per pet for the entire stay.

Bed

Bath

Sleeps

$576.12

/ Nightly

Private Vacation Home

Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace

Windham, New York, United States

brThis is a beautiful log home on 8 acres with amazing views of Windham Mountain. The home is a unique one that is made of Canadian pine whole logs that are over 30 inches in diameter. The residence contains 4 bedrooms and 3 full baths. The home is set on a private lot surrounded by trees on three sides, while offering the convenience of town only 5 minutes away.brbrNew for 2025: Weber 3-burner propane grill, upgraded seating and lighting for the outdoor fire pit, new hammock, and a larger TV in the lower level. br brThe house features a direct, unobstructed view of the Windham Mountain resort. It is the ideal retreat for your family, friends and loved ones to enjoy all that the Catskills has to offer.brbrAre you looking to prepare and cook a big meal for a dozen people Our home has everything you need to make a memorable occasion. The kitchen contains full sets of quality pots and pans in lots of sizes, knives and cutting boards, flatware, dish ware, and serving bowls and platters. There also lots of tools for the outside grill. The home is well stocked with various spices, oils, flour, bread crumbs, and coffee filters. There are always extra condiment supplies just in case someone forgot something- which always happens! The big table inside has two leaves that extend the table to 12 feet long. And the big table outside on the deck is a great gathering spot in warmer weather. brbrThe kitchen and buffet table are stocked with wine, margarita, and martini glasses along with a set of cups for Moscow mules. There is a cocktail shaker, whiskey glasses, and plenty of wine openers. brbrYou just have to bring your own food and drinks! brbrChildren- If you are visiting with younger ones, there is an air fryer for quick cooking and we have full sets of plastic cups and plates along with kid sized utensils. Kids love the large divided plates that we have, too. There are three safety gates located at on the stairs. Remember to watch them when the hot tub cover is opened. brbrThe fireplace is stocked with lighters and kindling ready to go. There is dry firewood on the deck for your use.brbrStep out the back door and you will find yourself on a spacious wood deck with a view that directly faces the mountain and a 15 mile view. This home has a 6 person outdoor hot tub and a large fire pit area, a covered deck with an extra large dining table for 10 and an outdoor fireplace, fabulous sunsets, and a giant lawn for playing games. There is plenty of room for cornhole or wiffleball games.brbrIf BBQ-ing is your thing, we have you covered with a propane grill. An extra tank is provided in case the one there runs low and needs to be swapped out. brbrA few steps down to the back yard is a fire pit surrounded with chairs, stools, and string lights for your entire group to gather around. We provide you with a fire starter kit and a decent amount of wood for multiple nights gathering around the fire pit.brbrThere is a radiant heat system throughout the entire home, in addition to forced air heating and 2 separate central air conditioning systems. There is a 10kw Generac generator on site so you don't have to worry about losing electricity during your stay. There is high speed Internet/ Wifi for you and your group to easily stream on multiple devices. brbrThe property is a 5 minute drive to the ski resort, hiking and biking trails. In the summer Windham is known for hiking, golfing, mountain biking, fly-fishing, and a nearby water park. Of course, in autumn, the foliage is just spectacular. This property is conveniently located:brbr- 3 to 4 minutes away from the village of Windham.br- 5 minutes away from Windham Mountain Resortbr- 15 minutes away from Hunter Mountain Resort and village of Tannersvillebr- 20 minutes to North-South Lake, Kaaterskill Falls, East Durham, Colgate Lake State park, Greenville Drive-in, and Zoom Flume Water Park.br-25 minutes from the NYS Thruway exit 21 and Village of Catskillbr-30 minutes to Hudson, Phoenicia, and Saugertiesbr-40 minutes from Woodstock, NYbrbrOther Things to Note:brbrCHECK INbrThe check-in will be contactless and keyless. Before you arrive, we will send you the code to the door lock.brbrPARKINGbrPlease feel free to utilize the parking spaces nearest to your house for the duration of your stay - it can hold up to 6 cars. Note that we are not responsible for personal items left in your car. We strongly encourage the use of all wheel or 4 wheel drive vehicles during snow season as the driveway does have a slope to it.brbrHOUSE ACCESSbrThe entire house is yours for the length of your stay. Feel free to enjoy the private deck, fire pit and seating areas around the yard.brbrCHECK OUTbrOur check-out time is at 11:00 am. Late checkouts are available upon request. Please make sure to do the dishes before you leave but it’s ok to place the remaining dishes in the dishwasher and start the cycle. Please strip the bedsheets and leave them with any used towels by the laundry room. Don’t forget to do a final walk thru of the house to make sure you haven’t left behind any personal items.brbrRECYCLINGbrGuests can leave the recycling items on a separate bag in the deck box outside by the kitchen. The cleaning team will take care of it after guests leave.brbrITEMS LEFT BEHINDbrPlease note that we are not responsible for any items left behind. We will make every effort to search and find your forgotten items after you check out, but we do not guarantee if they can be found.brbrFRIENDS OF MOTHER NATUREbrPlease note that we are located in the countryside, surrounded by trees and foliage. Although we have regularly scheduled pest control services in and around the home and yard, you are still likely to see a few insects or other living beings from Mother Nature. brbrPETSbrWe have a no pets policy. Some prior guests assured us that their dogs were well behaved and they were not.

Bed

Bath

Sleeps

$248.01

/ Nightly

Private Vacation Home

Ski, Hike & Golf: Pet-Friendly Windham Retreat

Windham, New York, United States

2 Mi to Windham Mountain Club | Furnished Deck | Peaceful, Wooded Surroundings | FireplacebrbrSurrounded by lush woodlands in the heart of the Catskill Mountains, this 3-bed, 2-bath vacation rental in Windham is the ideal base for year-round thrills, from scenic hikes to Kaaterskill Falls to skiing at Hunter Mountain Resort. This home features a full kitchen, a cozy living area with a fireplace, and a furnished deck for family BBQs. When you’re ready to explore, visit the shops downtown!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 full bedbr- Bedroom 2: 1 king bed br- Bedroom 3: 2 twin beds brbrOUTDOOR LIVINGbr- Upper & lower deckbr- Gas grill, outdoor lounge furniturebrbrINDOOR LIVINGbr- Flat-screen TVbr- Fireplacebr- Dining table, deskbr- 2 walk-in showersbrbrKITCHENbr- Stove/oven, refrigerator, dishwasherbr- Cooking basics, dishware/flatware br- Single-serve pod coffee maker, toaster oven brbrGENERAL br- Free WiFibr- Electric heating, ceiling fansbr- Complimentary toiletries, hair dryerbr- Washer/dryer (basement), hangers, iron/boardbr- Linens/towels, trash bags/paper towels brbrFAQbr- Pet fee (paid pre-trip)br- No A/CbrbrACCESSIBILITYbr- Multi-level home, 6 steps to enterbr- Bedroom & bathroom on main level br- 4 interior steps to access living room br- Interior staircase required to access bedrooms, bathroom & laundry area on upper & lower levels brbrPARKINGbr- Driveway (4 vehicles)brbr-- THE LOCATION --brbr- Secluded location close to fishing, boating & horseback riding br- 2 miles to Downtown Windham: Windham Fine Arts, Windham Theatre, dining, breweries, shopping, farmers market, seasonal events & festivalsbr- 8 miles to Zoom Flume Water Park br- 12 miles to Hunter Mountain Resortbr- 18 miles to Kaaterskill Fallsbr- 47 miles to Albany International Airportbrbr-- 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 smoking br- Pet friendly w/ $50 fee (+ fees & taxes) br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This multi-level home requires 6 steps to enter. While it features a bedroom and bathroom on the main level, 4 interior steps are required to access the living room, and an interior staircase is required to access the bedrooms, bathroom, and laundry area located on the upper and lower levelsbr- This property does not offer air conditioning

Bed

Bath

Sleeps

$1690.2

/ Nightly

Cabin

Lux Mansion, Windham: Hot Tub, Sauna, Cold Plunge

Windham, New York, United States

❆ Experience the ultimate retreat at Ulula Eco Resort, where luxury meets nature in the scenic Catskills. This 4770 sq. ft chalet, made entirely of eco wood, features plush king-sized beds and a gourmet kitchen. Enjoy breathtaking views and top-notch amenities like a ground-level hot tub, sauna, cold plunge and cozy fire pit. Perfectly situated near Windham Ski Resort, it's the ideal base for skiing or serene mountain escapades.brbr༄ bWelcome to Ulula Eco Resort: Your Luxurious Catskill Sanctuary/bbrbrbUnique amenities: Cold plunge and sauna/bbrbrLocated in the heart of Windham, close to the Windham Ski Resort and the majestic Catskill Mountains, Ulula Eco Resort offers the perfect blend of adventure and relaxation. This eco-friendly retreat, crafted from 100% eco wood and adorned with hardwood oak flooring, spans a generous b4770 square feet/b. With its bsix bedrooms and four bathrooms/b, the resort is ideally configured to accommodate gatherings of families and friends alike.brbrbOur Favorite Features at Ulula Eco Resort:/bbr→ Majestic views of the Catskill Mountains from every roombr→ Wi-Fi throughout the propertybr→ Environmentally conscious design with natural wood constructionbr→ Luxurious king-size beds in five bedroomsbr→ Modern electric fireplace and professional pool tablebr→ Smart TVs for streamingbrbrbThe Chef’s Dream Kitchen is Fully Equipped with:/bbr→ State-of-the-art appliancesbr→ Large center island with seatingbr→ Custom wood cabinetry and sophisticated designbr→ Outdoor Weber propane grill and charcoal kebab grillbr→ Essential cookware and bakewarebr→ Coffee station with a selection of machinesbrbrbOutdoor Features Designed for Leisure and Celebrations:/bbr→ Ground-level hot tub for relaxing under the starsbr→ Cold plunge & Saunabr→ Fire pit area ideal for cozy eveningsbr→ Gourmet outdoor cooking with high-end grillsbr→ Comfortable seating and atmospheric patio lightsbrbrbSleeping Arrangements for Comfort and Privacy:/bbr→ Master Suite on Main Level: King-size bed, full ensuite bathroom with double sinks.brManaged by @outof_urban.brIf this property is unavailable for your dates, please visit our profile to explore many other beautiful homes we’d be happy to host you in.brbr→ First Floor Master Bedroom: King-size bed, full ensuite bathroom including a tub and shower.br→ First Floor Bedrooms #3, #4, and #5: King-size beds with shared bathroom access.br→ First Floor Bedroom #6: Two bunk beds, perfect for kids or singles.brbrbStay Connected and Informed:/bbrDon't miss out on seasonal activities in the area!brbrbrLocated in the scenic Catskill Mountains, Windham, New York, is known for its captivating natural beauty and a wide array of outdoor activities. This charming neighborhood is a prime destination for adventure enthusiasts and those seeking a peaceful retreat from the urban hustle. Windham is celebrated for its excellent ski resorts, vibrant local festivals, and numerous hiking trails that offer panoramic views. The area also boasts fine dining options, quaint shops, and a welcoming community that embodies the warmth of small-town living. Whether you're here for thrilling ski adventures or tranquil nature walks, Windham provides a perfect backdrop for a memorable getaway.brbrOther things to notebrbr**IF YOUR DATES ARE UNAVAILABLE, MESSAGE US ABOUT OTHER HOMES**brbr• If you declined VRBO’s travel insurance, we strongly recommend purchasing your own through a third-party provider. Please note that our cancellation policy is strict, and we are unable to issue refunds for unexpected travel delays or changes, emergencies, weather conditions, illness, or any other travel-related circumstances.br• To confirm reservation, all guests must provide ID information.br• All guests should sign the additional agreement before check-in - Guest Liability Waiver and ReleasebrIf guest refuses to do so, the host has the right to cancel booking through support teambr• No shoes in the housebr• Smoking is prohibited in the house, including electronic cigarettes. Fine for violation - $1000br• All National Holidays Require 3 nights stay minimumbr• Minimum booking age 25 years old.brbrPet PolicybrbrWe’re happy to welcome your furry companions! Please review our pet guidelines below:brA $99 pet fee per stay applies (for one pet)brA maximum of 2 pets is allowedbrPets are not allowed on beds, couches, or any furniturebrFailure to follow these rules will result in a $500 deep cleaning fee.brWe appreciate your cooperation in helping us keep the home clean and comfortable for all guests.

Bed

Bath

Sleeps

$744.33

/ Nightly

Private Vacation Home

Unwind Windham, Chalet

Windham, New York, United States

pWelcome to strongUnwind Windham/strong, a stunning mountain chalet designed for relaxation and adventure.brbr/pbrbrpTucked away in the heart of the Catskills, strongUnwind Windham/strong is more than just a place to stay—it’s a retreat designed for those who crave both adventure and relaxation. /pbrbrpWake up to crisp mountain air and breathtaking views, spend your days exploring the slopes or wandering through nearby vineyards, and wind down with unforgettable evenings surrounded by nature./p

Bed

Bath

Sleeps

$468.26

/ Nightly

Private Vacation Home

Large Catskill townhome steps from skiing w/pool

Windham, New York, United States

Come enjoy the Catskills at our spacious Windham Mountain townhome at the base of Windham Mountain. Townhome includes 4BR, 3BA with a big open living area and deck. Only a short walk to the lifts and the center of Windham is just 1/2 mile away. The complex includes a beautiful indoor pool and hot tub + newly renovated clubhouse with gym. Early check-in or late check-out may be available upon request depending on other bookings.

4

Bed

3

Bath

12

Sleeps

$1110.86

/ Nightly

Private Vacation Home

Fully updated townhome 200 feet from slopes of Windham Mountain

Windham, New York, United States

This 3-bedroom 3 bath townhome 200 feet from the Windham ski lift is perfect for your escape. With a king bed, 2 bunk beds, and a first floor queen bedroom with a desk, this amazing property offers a relaxing retreat for guests. Enjoy the convenience of walking to the lifts on your own schedule. Avoid worrying about parking and where to store your stuff, even a spot to dry the boots. Come home for lunch or stay late for aprés all just a few steps from the door. We look forward to hosting you at our home.

Bed

Bath

Sleeps

$477.0

/ Nightly

Condo

Near Hunter and Windham ski resorts. Crystal Pond town house, 4BR & 3.5 bath

Windham, New York, United States

This is our family's home away from home. We mostly use it in the summer and once in a while for skiing. Having kids who are always busy with sports means the house ends up sitting vacant too much. Therefore, we would like to offer this home for you to enjoy as much as we do. This home was finished with all the high-end features such as granite counter tops, stainless steel appliances and hardwood floors. This is a 4 bedroom town house that has 3 and a half baths and is located 3 miles from Windham Mountain Resort and 5 miles from Hunter. This condo has a fully equipped kitchen with counter seating for 4 people and a table that seats 6 people. A stone fireplace, Cable TV, DVD, and Wifi are all included, along with a front load full size Washer/Dryer. There is a shuttle service to Windham Mountain on weekends and holidays during the ski season. The shuttle operates between 8 am to 5 pm. It sleeps 8. No Smoking and No Pets. All of the bedrooms have QUEEN beds.

Bed

Bath

Sleeps

$294.84

/ Nightly

Private Vacation Home

Windham Family Getaway

Windham, New York, United States

This three bedroom, two bath home with many new amenities and a wood burning stove sleeps up to 9 people (max 8 adults) with the pull out sofa. Less than one mile from the base lodge of Ski Windham and a half mile north of Main St., this home provides scenic views and the perfect place to stay for your getaway any season of the year. Ideal for a quiet vacation with your family. The spacious 12'x20' elevated deck faces The Ski Windham slopes. Home is accessable for the mobility challenged, with a wheel chair lift, a ramp for the front door and a low step shower stall with a seat.brbrIn the winter season, we are minutes from the slopes and the wood burning stove makes for cozy evenings after a day of skiing or snowboarding. In warmer weather, go hiking at many nearby trails, or swim in scenic lakes. Back at the house, bbq in the picnic area and enjoy dinner on the deck, followed by roasting marshmallows for s'mores in the fire pit. Be sure to download the star map tracker app to show the kids the constellations in the night sky!brbrLocated on 3 acres, there is plenty of room to explore behind the home. However, since there are neighbors nearby, we do not allow large gatherings or excessive outdoor music/noise. We are not interested in renting to young adults looking to party. The exterior of the house is monitored with a security camera system for both our protection and yours. Fines for non-compliance will be assessed.

3

Bed

2

Bath

9

Sleeps

$370.78

/ Nightly

Private Vacation Home

Secluded Cabin with Hot Tub 5 Min to Windham Mtn

Windham, New York, United States

Summary:brbrFind your perfect Catskills retreat at 31 Koonan Rd, a modern yet cozy mountain escape tucked away in a peaceful, secluded setting—just 5 minutes from Windham Mountain. This inviting 4-bedroom, 2-bath home blends contemporary design with rustic warmth, offering everything you need for relaxation, adventure, and quality time with loved ones.brbrbrbrThe Space:brbrEscape to 31 Koonan Rd, a secluded 4-bedroom home just 5 minutes from Windham Mountain. Downstairs has 3 bedrooms and 1 bath. Upstairs has 1 bedroom and 1 bath. With a hot tub, fire pit, deck, and wood stove, this modern mountain retreat is ideal for families and groups seeking both comfort and privacy. Enjoy peaceful forest views, unwind after skiing, or explore nearby Windham (5 mins) or Hunter Mountain (15 mins), hiking trails, and local restaurants. Whether you’re here for adventure or relaxation, this cozy getaway combines modern comforts with the quiet charm of the Catskills. brbrbrbrAfter a day on the slopes or trails, soak in the private hot tub, gather around the fire pit, or enjoy a fun evening of grilling and stargazing. For those who like to stay active, the home includes an exercise bike—perfect for a quick morning workout before heading out to explore.brbrLocated minutes from Windham and Hunter Mountains, this home offers easy access to skiing, hiking, streams, and local restaurants and wine bars. Whether you’re planning a family getaway, a ski trip with friends, or a peaceful work-from-retreat, 31 Koonan Rd delivers the perfect balance of privacy, comfort, and modern convenience.brbrbrbrLook forward to hosting you.brbrbrbrGuest Access:brbrEntrance is on 1st floor, a code will be provided 24 hr before check in. Access to the deck from inside 2nd floor or via stairsbrbrbrbrOther Things to Note:brbrFirewood is not provided, but sold at most convenience stores in town,brbrbrbrInteraction with Guests:brbrCheck out our house manual which offers a guide on all information concerning the home and the area. brbrPlease message us on your booking platform for any and all questions! brbrWe are quick to reply. Host contact information provided for emergencies..

Bed

Bath

Sleeps

$711.69

/ Nightly

Private Vacation Home

5 Bedrooms 5 1/2 Bath Ski Area Views, Walk to Skiing, Huge Common Space & Decks!

Windham, New York, United States

Unit 3: This brand new 3600 square foot townhome boasts 5 bedroom and 5 1/2 baths directly across from Windham Mountain. Since every bedroom has its own bathroom (4 of which are en-suite) everyone will have their own space! During the winter you can walk to skiing and the adventure park. But if warmer weather is for you then ride your mountain bike right out of your front door or drive a mile to the golf course. You can enjoy 365 day views of the ski area from 1000 square feet of outdoor decks. Although the spacious kitchen/dining/living area can accommodate large families or groups if you want to give everyone a break from cooking and cleaning you can enjoy all that Main Street has to offer less then a half mile away. Personal door code will be provided upon booking.

5

Bed

5

Bath

14

Sleeps

$363.04

/ Nightly

Private Vacation Home

Mtn-View Home w/ Deck on 4 Acres in Windham

Windham, New York, United States

5 Mi to Windham Mountain Club | Remote Workers Welcome brbrTucked away in the heart of Windham, this 3-bedroom, 2-bath vacation rental is the ideal base for epic ski days, scenic hikes, and fishing adventures! This modern home features a full kitchen, a cozy living area with a Smart TV for family movie nights, and a furnished deck with sweeping mountain views. When you’re ready to explore, visit the shops downtown or take the kids to Zoom Flume Water Park!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bed br- Bedroom 2: 1 queen bed br- Bedroom 3: 1 full bed, 1 twin bed brbrOUTDOOR LIVINGbr- Deck, covered porchbr- Outdoor seating, patio umbrellabr- Fenced-in yard spacebr- 4 acres, mountain views brbrINDOOR LIVINGbr- Smart TV w/ cablebr- Dining table, desk w/ computerbr- Walk-in closet, walk-in shower, shower/tub combobr- Stereo, board gamesbr- Wood-burning stovebrbrKITCHENbr- Stove/oven, refrigerator, dishwasherbr- Cooking basics, dishware/flatwarebr- Keurig, water filter, ice makerbr- Blender, microwave, toaster ovenbrbrGENERAL br- Free WiFibr- Baseboard heating, ceiling fans br- Washer/dryer, laundry detergent, hangersbr- Linens/towels, trash bags/paper towelsbrbrFAQbr- No A/C br- 2 exterior security cameras (facing out)brbrACCESSIBILITYbr- Single-story home, 3 steps to enterbr- 4 interior steps to access main living spacebrbrPARKINGbr- Garage (1 vehicle)br- Driveway (4 vehicles)brbr-- THE LOCATION --brbr- Private location close to hiking, golfing, fishing & horseback riding br- 4 miles to Downtown Windham: Windham Fine Arts, Windham Theatre, dining, breweries, shopping, farmers market, seasonal events & festivalsbr- 6 miles to Zoom Flume Water Park br- 14 miles to Hunter Mountain Resortbr- 47 miles to Albany International Airportbrbr-- 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 smoking br- No pets allowed br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires 3 steps to enter and 4 interior steps to access the main living space br- The property has ceiling fans but does not offer air conditioning br- Your safety matters. This property features 2 exterior security cameras: 1 camera is located on the garage facing the garage/driveway, and 1 camera is located by the front door facing the outdoor entryway/porch. The cameras are outward facing and do not look into interior spaces. The cameras actively record video and sound while guests are in residence

Bed

Bath

Sleeps

$364.5

/ Nightly

Private Vacation Home

Cozy Family-Friendly Townhouse Steps from Windham Mountain Resort - Unit 87

Windham, New York, United States

Important Notesbrbr Lift Tickets: For guests visiting during ski season, be sure to purchase lift tickets in advance through windhammountainclub.com. brbr⸻brbrAbout the TownhousebrbrWelcome to our fully furnished, two-bedroom, two-bathroom townhouse in Windham Mountain Village — just steps away from Windham Mountain Resort and minutes from town. The home offers everything you need for a comfortable, family-friendly stay, complete with a wood-burning fireplace, fully equipped kitchen, and private deck with a gas BBQ.brbrLayout & Sleeping Arrangementsbr• First Floor Bedroom: Two sets of bunk beds (3 Twin / 1 Full) + 2 Twin trundle bedsbr• Second Floor Bedroom: One Queen bed with private full bathroombr• Living Room: Pull-out Full-size sofa bedbrSleeps up to 9 guests comfortablybrbr⸻brbrLiving Room Featuresbr• 55” Smart TV with local cable channels and access to streaming apps (Netflix, Disney+, YouTube, Pandora, etc.)br• Wood-burning fireplace for cozy nightsbr• Free Wi-Fibr• DVD, CD, and VCR playerbrbr⸻brbrKitchen Amenitiesbr• Full-size refrigerator, oven, and dishwasherbr• Coffee/Espresso makerbr• Fully stocked with pots, pans, glassware, and utensils — everything you need to cook and dine inbrbr⸻brbrAdditional Featuresbr• Washer/Dryer in the first-floor bathroombr• Private deck with gas BBQ grillbr• Guaranteed parking for 2 cars + guest parking when availablebr• No pets. No smoking. Minimum age to rent: 25brbr⸻brbrLocationbrbrJust a short drive to the town of Windham, where you’ll find charming restaurants, shops, and local conveniences. Enjoy easy access to Windham Mountain Resort, hiking trails, and outdoor attractions year-round.brbr⸻brbrThings to Do Nearby (Weather Permitting)br• Indoor community pool & hot tubbr• Skiing, cross-country skiing, and snowshoeingbr• Windham Mountain Adventure Park – tubing, ziplining, ice skating, and kids’ snowmobilesbr• On-site tennis courtsbr• Windham Country Club Golf Course (1 mile away)br• Kaaterskill Falls and North/South Lake Campground (approx. 15 miles away)br• Mountain biking and scenic hiking trails nearbybrbr⸻brbrThis townhouse is one of two nearly identical homes we own in Windham Mountain Village. If your dates aren’t available, please check our other listing (Unit 33)!brbr Follow us on Facebook: @Windham Mountain Cabin Vacation Rental

Bed

Bath

Sleeps

$1212.1

/ Nightly

Chalet

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

Windham, New York, United States

Escape to a private luxury retreat in the Catskills—designed for families and groups seeking space, privacy, and meaningful time together.brbrThis 3,300 sq. ft. chalet features 4 ensuite bedrooms, a heated pool (May–Nov), hot tub, sauna, and sweeping mountain views. Just 5 minutes from Windham Mountain, it offers the perfect balance of nature, comfort, and elevated design.brWhether you're planning a weekend escape, ski trip, or special gathering, Black Bear Cabin is where lasting memories are made.brbrbrA Private Retreat Designed for ConnectionbrWelcome to Black Bear Cabin—a refined mountain escape where architecture, nature, and comfort come together effortlessly.brbrSet against direct views of Windham Mountain, this 3,300 sq. ft. chalet was designed for those who value privacy, space, and a seamless group experience.brbrFrom the moment you arrive, every detail invites you to slow down, reconnect, and fully enjoy your time together.brbrSpace & Privacy Without CompromisebrFour bedrooms, each with its own private ensuite bathroombrExpansive layout ideal for families, multi-family stays, and retreatsbrThoughtfully designed to balance togetherness and personal spacebrbrElevated LivingbrThe main living space features vaulted wood-paneled ceilings, a grand stone fireplace, and a dramatic arched window framing the mountain.brbrIt’s a place to gather after a day outdoors—whether for conversation, quiet moments, or simply enjoying the view.brbrDesigned for Gathering and HostingbrFully equipped chef’s kitchen with wine fridgebrLarge dining area with fireplacebrOutdoor dining patio with BBQ and pizza ovenbrbrPerfect for long dinners, shared meals, and effortless entertaining.brbrEntertainment, Seamlessly Built InbrDedicated recreation room with pool table, poker, and gamesbrSmart TVs with Dolby sound + SONOS throughoutbrPeloton and fitness areabrbrEverything is designed so your group never needs to leave to enjoy the experience.brbrWellness & RelaxationbrHeated saltwater pool (mid-May through November, weather permitting)br7-person hot tubbrBarrel saunabrbrA private, spa-like setting to unwind in every season.brbrThoughtfully Family-ReadybrCribs, high chair, and children’s essentialsbrSpacious layout ideal for families traveling togetherbrSafe, private outdoor environmentbrbrThe property is professionally treated to help minimize tick exposure and maintained with preventative measures; however, as with any natural setting, we cannot guarantee a tick-free environment and encourage appropriate precautions during your stay.brbrOutdoor LivingbrExpansive deck with Adirondack seatingbrFire pit for evenings under the starsbrSouthern exposure for natural light throughout the daybrUnobstructed mountain viewsbrbrPrime Locationbr5 minutes to Windham Mountain Clubbr20 minutes to Hunter MountainbrClose to hiking, golf, dining, and year-round outdoor activitiesbrbrOptional Elevated ServicesbrEnhance your stay with curated add-ons available upon request:brbrPrivate chef experiencesbrIn-home massagebrPrivate Yoga sessionsbrSki and winter activity packagesbrPre-arrival arrangements brbrThe ExperiencebrBlack Bear Cabin is more than a place to stay—it’s a setting designed for connection, celebration, and time well spent.brbrGuest accessbrGuests enjoy full private access to the entire 3,300 sq. ft. property, including all indoor and outdoor spaces—pool, hot tub, sauna, decks, and recreation areas.brbrSelf check-in via secure smart lockbrNo shared spacesbrA small number of owner closets and the outdoor shed remain locked for maintenance purposesbrbrInteraction with guestsbrYour stay is designed to feel effortless and private.brbrWe offer seamless self check-in and will not be present at the property during your stay. However, we are always available and responsive via the app or phone for anything you may need—from recommendations to assistance—ensuring a smooth and enjoyable experience from start to finish.brbrOther details to notebrbrProperty & SafetybrExterior security cameras are installed in outdoor areas (including driveway and pool/hot tub zones) for safety and property monitoringbrThere are no cameras inside the homebrbrCheck-In & Check-OutbrCheck-in: 4:00 PMbrCheck-out: 11:00 AMbrEarly check-in / late check-out may be available for an additional fee upon request after bookingbrbrHouse StandardsbrTo maintain the quality and experience of the home:brbrNo parties or eventsbrNo smoking or vaping anywhere on the propertybrRegistered guests only; no unauthorized visitorsbrQuiet hours must be respected, especially in the eveningbrbrThese standards are strictly enforced to ensure a peaceful environment for all guests and neighbors.brbrBooking RequirementsbrPrimary renter must be 30+ years oldbrThe booking guest must be present for the duration of the staybrbrPool, Hot Tub & SaunabrUse is at your own risk; children must be supervised at all timesbrNo glassware permitted in outdoor wellness areasbrUsage hours apply to ensure safety and respect for neighborsbrbrHousekeepingbrFresh linens and towels are provided at arrivalbrDaily housekeeping is not includedbrbrGuest ServicesbrOptional services available upon request:brbrPrivate chefbrIn-home massagebrAdditional baby equipmentbrbrHoliday BookingsbrA 7-night minimum applies for Thanksgiving, Christmas, and New Year’s staysbrDiscounts available for extended staysbrbrBooking & House GuidelinesbrTo ensure a smooth and high-quality experience for all guests, we follow a simple pre-arrival process.brbrAfter booking, guests will receive a brief summary of house guidelines and be asked to complete a standard rental agreement and provide a valid photo ID for verification.brbrThis is a quick and secure step, typical for professionally managed homes, and helps us maintain the quality, safety, and privacy of the experience for everyone.

Bed

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Sleeps

$3365.28

/ Nightly

Cabin

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms

Windham, New York, United States

This Windham cabin minutes from Hunter and Windham Mountains, boasts 6 inviting bedrooms, including 1 king bed, 4 queen beds, and 3 bunk beds. With amenities like WiFi, heating, and a washing machine, guests can relax and unwind in this beautiful retreat. The 7 bathrooms ensure everyone has their own space to freshen up. Guests can enjoy scenic views, total privacy, sprawling landscape and truly beautiful hiking trails all on the property. Everything you need for a short or extended stay is here on the property. With local vineyards and 2 ski mountains within 20 minutes, it is truly a year round getaway for anyone looking to relax and decompress. The town is about 5 minutes drive and boasts upscale as well as family dining options, local markets and merchants, and just about anything you might need during your stay. Fall in love with Windham and enjoy the magic it has to offer.

Bed

Bath

Sleeps

$595.24

/ Nightly

Private Vacation Home

Slope Views: Luxe Windham Retreat w/ Hot Tub!

Windham, New York, United States

Multiple Living Spaces | Outdoor Entertainment Area | Windham Mountain Ski ResortbrbrLocal wineries, delicious eateries, and all the beauty of the Catskill Mountains will be right at your fingertips when you stay at this lovely 5-bedroom, 3-bath home. Ideal for large groups, this Windham vacation rental offers a walkable location near the main street and mountain. After a day of exploring, you can relax in the hot tub, dine al fresco, or gather by the fire pit for s'mores and stargazing!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 king bedbr- Bedroom 3: 1 twin bunk bedbr- Bedroom 4: 1 twin bunk bed, 1 bunk bed (twin/full) w/ 1 full trundlebr- Bedroom 5: 1 queen bed, 1 twin futonbr- Sleeping Nook: 1 twin futonbr- Additional Sleeping: 1 portable crib/pack n' playbrbrINDOOR LIVINGbr- 4 Smart TVs, game room w/ foosball tablebr- Wood-burning fireplace, 2 electric fireplacesbr- Dining table, breakfast barbr- Family room, mudroom w/ ski storagebr- Kids’ room, board games, books, kids’ toys,brbrOUTDOOR LIVINGbr- Deck w/ private hot tubbr- Outdoor dining area, gas grill (propane provided)br- Backyard, fire pit w/ seating, hiking trail access on-sitebr- 6 mountain bikes (bring your own helmet)br- Outdoor dinnerware & drinkwarebr- Commercial-grade bounce house (w/ addt'l fee)br- Golf course viewsbrbrKITCHENbr- Stainless steel appliancesbr- All major appliances, including dishwasherbr- Microwave, blender, Crockpot, toaster ovenbr- 2 drip coffee makers, toasterbr- Dishware/flatware, cooking basicsbr- Trash bags/paper towelsbrbrGENERALbr- Free WiFibr- Linens, towelsbr- Complimentary toiletriesbr- Central A/C & heatbr- Washer/dryer, hangersbr- Electric heatingbrbrACCESSIBILITYbr- 2-story homebr- 2 steps to enterbr- 2 bedrooms & 2 bathrooms on 1st floorbrbrPARKINGbr- Driveway (5 vehicles)br- RV/trailer parking allowed on-sitebrbr-- THE LOCATION --brbr- Catskills setting close to golfing, mountain biking & hikingbr- 0.3 miles to Trailway Bus Routebr- 0.5 miles to Windham Mountain Ski Resortbr- 0.7 miles to Windham Country Clubbr- 63 miles to Albany Int'l Airportbrbr-- 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- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires 2 steps to enter and offers 2 bedrooms and 2 bathrooms on the 1st floorbr- A commercial-grade bounce house is available to rent for an additional fee of $100 for 48 hours

Bed

Bath

Sleeps

$259.2

/ Nightly

Condo

Cozy Gateway Gem for 2 at Widham

Windham, New York, United States

A beautifully renovated condo at the Quads. Almost 600 sq of living space to your disposal with a separate bedroom and a living room with fireplace, which opens to a sizable deck overlooking the tennis courts and the pool in the distance. brbrBright and airy, tastefully updated. It is a first floor living so you do not need to deal with any interior stairs. The space flows nicely and offers a great location in Windham.brbrThis is a cozy 600 square foot one bedroom apartment, newly updated and furnished. it has a sizable balcony with the deck furnitures and a BBQ. brbrIt is a great space for 2 but 4 can easily be accommodated. A super comfy Brookstone, queen size air mattress and feel like actual bed or even better, is offered as an extra bedding option.brbrThe condo is located in a perfect spot in Windham. It is less than 5 minutes drive from Windham Path, Windham Mountain, golf courses and state hike trails. brbrPrefect 4 seasons community. brbr12 minutes drive or so from Hunter. 15 minutes to Tannersville. 25 to Catskills.

1

Bed

1

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4

Sleeps

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