Home Vacation Home Rentals By Owner In Windham, NY

Showing 120 Of 125 Vacation Rentals
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Exceptional(25)

$3844.8

/ Nightly
Private Vacation Home

EXCLUSIVE, EXQUISITE & UNFORGETTABLE MOUNTAIN OASIS

Windham, New York, United States

Copper Ridge Estate | 9BR Luxury Mountain Retreat w/ Theater, Pool, Gym & ConciergebrbrSleeps 18 · 9 Bedrooms · 8+ Baths · Indoor Pool · 2.5 hrs from NYC · Windham, NYbrbr⸻brbrBOOK NOW for the 2025–2026 Ski Season!br2-week stays or full-season (5-month) rentals available.brbr⸻brbrExperience true 5-star mountain living in this 10,000+ sq ft luxury estate perched in the Catskills. Just 2.5 hours from NYC—but a world away from stress—this is your dream winter (or summer) escape.brbrWhether you’re skiing in Windham, hosting a private retreat, or relaxing with family and friends, this home was designed to impress.brbr⸻brbrWhat You’ll Love:brbr9 Spacious Bedrooms (incl. Bunk Room) — Sleeps 18brIndoor Heated PoolbrPrivate 12-Seat TheaterbrFull Gym & Game RoombrExpansive Great Room w/ Wood-Burning Fireplace & Mountain ViewsbrGourmet Kitchen + Breakfast Bar + Multiple Dining AreasbrThoughtful Design Touches & Cozy Lounges Throughoutbrbr⸻brbr Optional Concierge Services (extra fee):br   •   VIP Ski & Golf Accessbr   •   Private Instructorsbr   •   In-Home Spa Servicesbr   •   Personal Chef, Housekeeping, Serversbr   •   Restaurant Reservations & Private Eventsbr   •   Corporate Retreat Planning & MorebrbrLet us customize your luxury mountain getaway.brbrbrPlease note we do have exterior security cameras that are remotely monitored by our alarm company to ensure only registered guests are on the property. Guests are also able to view the same POV from home screen. brWe also have a camera in the pool and the hot tub- for insurance purposes.
Bed 9

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Bath 7

Bath

Sleep 18

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Exceptional(33)

$479.25

/ Nightly
Private Vacation Home

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 3

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Bath 2

Bath

Sleep 8

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Exceptional(9)

$376.92

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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 3

Bed

Bath 3

Bath

Sleep 10

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Exceptional(56)

$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 5

Bed

Bath 3

Bath

Sleep 12

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Exceptional(2)

$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 3

Bed

Bath 2

Bath

Sleep 6

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Exceptional(53)

$294.84

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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.
Bed 3

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Bath 2

Bath

Sleep 9

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$370.78

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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 4

Bed

Bath 2

Bath

Sleep 8

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$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 3

Bed

Bath 2

Bath

Sleep 6

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Exceptional(23)

$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 2

Bed

Bath 2

Bath

Sleep 9

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Exceptional(19)

$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 5

Bed

Bath 3

Bath

Sleep 17

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Exceptional(3)

$948.2

/ Nightly
Private Vacation Home

Lux Windham Getaway | Views & Indoor Heated Pool

Windham, New York, United States

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

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Bath 4

Bath

Sleep 16

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Exceptional(1)

$1478.51

/ Nightly
Private Vacation Home

Luxe 8BR Windham Lodge | Theater, Walk to Slopes

Windham, New York, United States

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

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Bath 6

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Sleep 16

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Exceptional(7)

$332.08

/ Nightly
Private Vacation Home

Windham Mountain Vacation Rental ~ 3 Mi to Lifts!

Windham, New York, United States

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

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Bath 2

Bath

Sleep 8

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