Vacation Rentals By Owner In Windham, NY

Summary:brEscape to the ultimate Catskills retreat at APRES HAUS! This 8-BR, 6.5-BA home on 10.5 acres features a natural swimming pond, indoor hot tub, chef’s kitchen and stunning mountain views. Comfortably accommodating up to 22 guests across 6,000+ sq feet and three floors, it's perfect for family reunions, retreats and intimate weddings. With an unbeatable location close to the ski resorts (Windham & Hunter), you'll have easy access to year-round activities like skiing, hiking, golf and more.brbrThe Space:brWelcome to APRES HAUS, your private Catskills getaway! Designed for large gatherings, this spacious home offers all the amenities you need for everyone in your group to relax, recharge and have fun. With a fully stocked chef’s kitchen featuring double ovens and dishwashers, as well as an 18-foot dining table, you’ll have no problem preparing and enjoying meals together. After dinner, sit around the wood-burning fireplace in the living room, take a rejuvenating soak in the indoor hot tub, or step onto the expansive deck for stunning mountain views (including 4 of the highest peaks in the Catskills). The home also offers a game room with pool table, foosball and darts, a SONOS sound system, as well as a large natural swimming pond and fire pit on the grounds. brbrAbout the Space:br- Fantastic location in the heart of the Catskills, close to multiple ski resortsbr- Indoor spa room with 8-person hot tubbr- Outdoor wood-burning fire pit with beautiful mountain viewsbr- Natural swimming pondbr- Comfortable sleeping for up to 22 guestsbr- Fully-stocked chef’s kitchen featuring 2 ovens and 2 dishwashersbr- 18-foot oak dining table seating 22br- Large outdoor deck with BBQ grill and plenty of seatingbr- Living room with vaulted ceilings, TV, wet bar and wood-burning fireplacebr- Game room with pool table, foosball, darts and morebr- Dedicated workspace and high-speed internetbr- Kid-friendly amenities: crib, pack ‘n play crib, high chair, safety gates, children’s books, games & dishwarebr- Eco Spa bath and body productsbr- Full-size washer and dryerbr- 2-car garage with additional parking outsidebrbrSleeping LayoutbrThe Mountain House sleeps 22 guests comfortably across eight dedicated bedrooms, including a kid-friendly bunk room - perfect for several families or all of your closest friends!br- Bedroom 1: Queen bed - Ensuite Bathroombr- Bedroom 2: Queen bed - Ensuite Bathroombr- Bedroom 3: Queen bed - Ensuite Bathroombr- Bedroom 4: Queen bed - Ensuite Sink/Vanitybr- Bedroom 5: Queen bed + Twin bunk beds + trundle bed br- Bedroom 6: 2 Twin beds + 1 trundle bedbr- Bedroom 7: Queen bed + Twin bunk beds + trundle bedbr- Bedroom 8: Queen bed + Twin bunk beds + trundle bedbrbrHome LayoutbrThis family-friendly home features all the amenities for your group to enjoy your stay! brbrMain Levelbr- Fully-equipped chef’s kitchen perfect for preparing group mealsbr- 18-foot dining table with seating for 22br- Cozy living room with access to the deckbr- Queen bedroom with sitting room, gas fireplace and TVbr- SONOS sound system throughout the floorbrbrUpper Levelbr- Queen bedroom with gas fireplace and private balconybr- Loft living room with TVbr- 2 bedrooms with full bathroombrbrLower Levelbr- Game roombr- Living room with TV, wet bar and wood-burning fireplacebr- 4 bedrooms and 3 full bathroomsbr- Stereo system throughout the floor, with volume control in each roombrbrGuest Access:brThe whole house. Locked doors or cabinet/closets with zipties are off limits. Ample parking for a large group.brbrThe Neighborhood:brSpectacular Views of the Catskill Mountains, Newly constructed Natural Swimming Pond! Every amenity you can think of: 22 person dining room table, pro grade kitchen, indoor hot tub, Game Room, The house was built to accommodate. 5 minutes to Windham Mountain and 20 minutes to Hunter.brbrGetting Around:brCar recommended; Can arrange car services if necessary.br40 minutes to Hudson Amtrakbr1 hour to Albany InternationalbrAdirondack Trailways bus service to the center of town.brbrInteraction with Guests:brAs much as is necessary, generally a meeting prior to check in to deliver the key and or greeting when you arrive for a tour of the house.

Chalet

Family-Friendly Windham Estate, Swimming Pond, Spa

Windham, New York, United States

Bed

Bath

24

Sleeps

$321.97

Walk to Main Street Shops & Restaurants | Amazing Bird Watching | Secluded Deck w/ GrillbrbrEscape to the mountains at this 3-bedroom, 2-bath vacation rental. Perfectly situated on Windham Mountain, this cozy yet stylish townhome is steps from the ski slopes, offering all-season adventure — including Catskill trails and lakes — right outside your door! Pet-friendly and packed with amenities, it’s the perfect base to explore Windham and neighboring gems like Hunter, Hudson, and Tannersville.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 full bed, 1 twin bedbr- Sleeping Nook: 1 twin floor mattressbrbrINDOOR LIVINGbr- Smart TVs, books/board gamesbr- Dining table, breakfast barbr- Fireplacebr- Laptop-friendly workspacebrbrOUTDOOR LIVINGbr- Private deck w/ seating & dining tablebr- Charcoal grillbr- Shed w/ inflatable kayak, saucers & sledbrbrKITCHENbr- Refrigerator, microwave, stove/oven, dishwasherbr- Drip coffee maker, toaster oven, blenderbr- Cooking basics, dishware/flatwarebr- SpicesbrbrGENERALbr- Free WiFibr- Central A/C & heatingbr- Linens & towels, trash bags & paper towelsbr- Complimentary toiletries, hair dryer, hangersbr- Washer/dryer, iron/boardbrbrFAQbr- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- 3-story townhome, 1 step required to enterbr- All bedrooms & full bathrooms on 2nd floor & in basementbrbrPARKINGbr- Reserved space (1 vehicle)br- Community lot (addt'l vehicles)brbr-- THE LOCATION --brbr- Near hiking & fishingbr- Close to local farmers markets, Windham Mountain Club & Peak Transport Trainbr- 1 mile to dining, shopping & movie theater in townbr- 2 miles to Windham Golf Clubbr- 8 miles to Batavia Kill River & 30 miles to Schoharie Creekbr- 11 miles to Zoom Flume Water Parkbr- 57 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 smokingbr- Pet friendly w/ $50 fee (+ fees & taxes, dogs only, max 2)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 3-story townhome requires 1 step to enter; interior stairs are required to access all bedrooms and full bathrooms on the 2nd floor and in the basement

Ski, Hike & More: Year-Round Gem in Windham

Windham, New York, United States

Bed

Bath

Sleeps

$1188.0

Easy walk to mountain and easy 1/2 mile drive to center of town. This 3 bedroom unit can sleep 10 people. There is an indoor heated pool with radient heated floors and a hot tub a short walk away. Working wood burning firelplace.

Condo

Immaculate & Cozy 3 BR at base of Windham Mtn

Windham, New York, United States

Bed

Bath

Sleeps

$540.32

This beautiful getaway in the heart of the Catskill mountain region is the perfect oasis for creating memories that will last a lifetime. Less than 5 minutes away from the Windham Mountain Ski Resort, this secluded water-front destination is perfect for nature lovers planning to enjoy all the amazing outdoor treats this area has to offer!brbrThis hidden gem provides plenty of space for adults and kids alike to enjoy the great outdoors, games, entertainment, and fun. Our full log house offers the epitome of rustic charm, secluded living, and the modern amenities you’re accustomed to. With Cable TV and Wi-Fi throughout, we’ve let no convenience go unaddressed. Enjoy meals without compromise in our fully functional kitchen equipped with stainless-steel appliances and stocked with plates, utensils, and lots of windows throughout for enjoying views and natural sunlight.brbrWhether you’re planning an outdoor excursion, looking for the perfect setting for an intimate wedding, a vacation for the kids, or just a memorable get together with friends and family, this secluded waterfront ski cabin provides everything that you’re looking for and more!brbrEnjoy the beauty that these 5 acres have to offer as you relax to the soothing sounds of nature and running water from the nearby freshwater stream. Bask in the warmth of the heated outdoor deck, while overlooking the freshwater pond or while catching a glimpse of the Windam Mountain Ski Resort. Guests can easily transition from indoor to outdoor entertainment with the wraparound deck which connects to the main deck, fully equipped with a gas grill, smoker, and lots of comfortable seating for guests.brbrWith ample amounts of open space for fun & entertainment, guests can even enjoy the warmth of a bonfire or roast marshmallows in the fireplace right next to the ¼ acre pond stocked with bass for catch & release fishing.brbrPamper yourself & unwind in the sauna that seats six or have fun with a game of foosball. Keep family & friends entertained with an array of board-games or spend quality time laughing, conversing, or enjoying your favorite beverage around the wood-burning fireplace. Whichever amenity you decide to enjoy, there are plenty to choose from here to help you create a truly memorable experience.brbrThe house is surrounded by wilderness and that means water supply is from the ground water, which can emit a smell, if you are uncomfortable with this we recommend bringing bottle water for drinking and cooking. In addition we use septic system to manage the waste, please use the water and waste system responsibly to avoid clogging the system.brbrYour destination awaits and is just minutes away from:bra. 3-4 mins away from Town and restaurantsbrb. 3-4 mins away from the Windham Mountain Resortbrc. 15-20 mins away from the Hunter Mountain Resortbrd. 20 mins to Colgate Lake State parkbre. 25-30 mins away to Kaaterskill Falls & TrailsbrbrFor your convenience, the home is maintained by compassionate hosts with a dedicated caretaker, happy to address any questions or concerns that you and your guests may have.

Cabin

Waterfront Secluded Log-house w/Sauna, Games, More, Mins To Town & Activities

Windham, New York, United States

Bed

Bath

Sleeps

$402.84

Welcome to Windy Hollow! A spacious and newly renovated vacation home with stunning views of Windham Mountain and walking distance to town. Thoughtfully designed to provide multiple gathering spaces for guests over two levels. We are ideally setup for families and groups. Ski the slopes, hike the trails, bike the mountain, enjoy a round of golf, swim in the lakes, jump in the waterholes, kayak, canoe, take the kids to the waterpark, savor the winery, get spoiled at the spa, relish the Maine Lobster Bake on Saturday nights in the summer or visit our many wonderful local bars/restaurants. However you decide to spend your vacation, Windy Hollow offers a home-away-from-home experience year-around.brbrWindy Hollow is a spacious home with a warm cozy feel just 0.8 miles from Windham Mountain, 10 miles from Hunter Mountain, and 30 miles from both Belleayre Mountain and Plattekill Mountain. The spaces were designed with our young family in mind and with the intention to make guests feel at ease. We hope your family and friends will enjoy the house as much as we do!brbrHouse Layout: brbrFirst Floor - One of our favorite spaces in the house is the main living room with high ceilings and a wood-burning stove. You can light a fire or play music and cozy up on the couch while overlooking the beautiful views from our oversized floor to ceiling windows. Taking just a few steps up leads to a spacious private game room for the littles to have their own space. They can play endless board games, read books, or log into any streaming channel on the already Wifi connected TV. Conversely, the space can also be used as a workspace to catch up on email or escape for some quiet time on the couch while fancying a book. brbrThe kitchen and dining area are a few steps up from the living room and feature all new appliances. A well stocked and fully equipped kitchen awaits those inner chefs. Plus a large island with three bar stools provides plenty of room for meal prep, baking, serving food and even enough room to make fresh pasta for the whole family! The dinning room table will accommodate a family of eight for shared meals. One of the fully renovated bathrooms is adjacent to the kitchen for convenience. brbrSecond Floor - All bedrooms are on this level with large closet space. The primary bedroom is a large room with a king size bed, private sitting area and a 65' SMART TV that is Wifi connected and ready for you to log into your streaming channels. Bedroom 2 accommodates up to four guests with a twin and full size bunk bed plus an additional twin bed. This bedroom features three custom windows allowing guests to take in the incredible views of the mountain. Bathroom 2 is fully renovated and located between bedroom 1 and bedroom 2 for easy access. Bedroom 3 is down the hall and features a comfortable queen size bed with large windows to take in the views from upstairs. The new washer and dryer are on this level and ready to use. brbrDuring the warmer months enjoy grilling on the large wraparound deck while peepers sing their love songs. Experience the darkest night sky as you fancy a nice cocktail and admire the endless stars. During the cooler months, relish by starring at the ski slopes from the large oversized windows in the living room while cozying up on the couch and sipping on a warm beverage, making Windy Hollow a perfect home during any season. brbrClose to: brbrWindham Mountain Club: 0.8 miles (6 EV charging stations)brUnion & Post Restaurant 0.8 miles Catskill Mountain Country Store: 0.8 milesbrWylder Hotel Windham 0.9 miles brBabblers Restaurant, Bakery & Bar 0.9 milesbrEastWind Lodge & Bar: 0.9 miles Prominence Restaurant: 1.2 milesbrWindham Country Club: 1.3 miles brThe Windham Path: 1.5 milesbrChicken Run Family Restaurant 1.5 miles Christman’s Windham House: 2 milesbrHayfield: 5.3 miles The Vineyard at Windham: 5.6 milesbrCD Lane Park: 5.7 milesbrWindham Manor: 5.7 miles Mountain Brook Farm: 7.4 milesbrHunter Ski Mountain: 10 milesbrFlume Zoom Waterpark: 10 miles Colgate Lake: 11 miles Tops Friendly Supermarket: 13 miles Hannaford Supermarket: 16 miles Kaaterskill Falls: 18 miles Rail Explorers Catskills: 24miles Belleayre Ski Mountain: 30 miles Plattekill Ski Mountain: 30 miles Hudson Amtrak Train Station: 30 miles Howe Caverns Adventures: 37 miles brbrWalking distance to: brbrThe Windham SpabrWindham DinerbrLa Patisserie NormandebrClutch & Throttle Main Street MarketbrTap House GrillebrZicatelas brThe Windham LocalbrMillrock Restaurant & Bar RoombrWindham PizzariabrMountain King Brewing Company. Lilly's Steaks & CocktailsbrThe Tipp TavernbrCarvel brSubwaybrWindham Movie Theater Gem Mercantile Country Boutique brWindham Liquor Store Chinese Garden Restaurant brbrWildlife in the Catskills - we are situated in the middle of the most beautiful area of the Catskills and nature abounds. You may likely see wildlife during your stay. brbrAll BBQ food items should be brought inside and the grill cleaned after use to avoid having unwanted visitors. Windy Hollow is regularly treated for pests, but being that we are surrounded by nature, it would not be unusual to see a few insects browsing on the deck.

NEW - Cozy Modern: Stunning views,3 mins ski,BBQ,Fire Pit,Game Room,walk to town

Windham, New York, United States

3

Bed

Bath

Sleeps

$719.57

Summary:brbrCarrotflower Farmhouse is a 5 bed, 4.5 bath farmhouse with a separate guest cottage just 2.5 hrs to NYC & a 15min walk to shops & dining in Windham village. This home features a hot tub, stone patio and views of Windham Mountain right from the living room, 2 rocking chair porches, and a peaceful setting with its own walking paths. Ski, relax, or enjoy world class hiking at this historic Catskills gem.brbrbrbrNearby towns:Windham (5mins), Hunter (20mins), Plattekill (35mins), Belleayre (45mins)brbrbrbrThe Space:brbrCarrotflower Farmhouse is a historic Catskills retreat that combines vintage character with every modern comfort. Built in the 1830s by Windham's founding family, the home is one of the town’s earliest landmarks and still one of its most special, retaining original details you won’t find anywhere else, amidst a stylish renovation throughout. brbrbrbrStart your day with a cup of coffee on the covered front porch, taking in the peaceful view of Windham Mountain and the valley below. Inside, the home features an 1880s great room with a brick hearth, vintage décor curated from Catskills and Hudson Valley antique shops, large windows, comfortable seating and an indoor dining area. The kitchen is professionally outfitted with all the tools you might need for a special meal with your group, and features a circular breakfast table. The cozy media room off the great room offers a tv and tons of games and puzzles to pass the time on a snowy night or summer evening. brbrbrbrOn the main floor, the primary bedroom features a king size bed and an ensuite bathroom with a shower/tub combo. Also on this floor is a guest bedroom offering a queen bed and an ensuite bathroom with a walk-in shower. This suite has its own private entrance if you desire, through a cozy office space that adjoins the bedroom. Upstairs there are two additional guest rooms, one with two double beds and one with a queen, sharing a bathroom with a walk-in shower.brbrbrbrA charming self-contained guest cottage sits steps from the farmhouse featuring a queen bed, full bathroom with a walk-in shower, kitchenette and a rocking-chair porch with private mountain views. Ideal for grandparents, couples, or anyone craving extra privacy.brbrbrbrOutdoors, sweeping mountain views set the stage for immersion in nature. The stone patio is hidden behind the home, creating a private outdoor escape that features a dining table and a 7-person hot tub and fire pit. Beyond the patio area, guests can wander the back fields, nap in hammocks, or enjoy Adirondack chairs at the hilltop overlook or on the front lawn. brbrbrbrWalkable to Windham’s best restaurants and shops, and just minutes from Windham Mountain Club, it’s the perfect mountain getaway. Families and friends seeking fresh air, skiing, hiking forest trails, antiquing in nearby hamlets, and relaxation will find no shortage of activities here, with a luxurious launching pad to explore the area. Carrotflower Farmhouse is more than a getaway, it’s a place to make memories that last.brbrbrbrThe property is equipped with a full house generator to ensure uninterrupted comfort during your stay plus WiFi controlled locks and thermostats. There is also a mudroom with ski racks.brbrbrbrThe Neighborhood:brbrCarrotflower Farmhouse places you right in the heart of Windham, steps from the town’s best offerings. Start your day with brunch at Babblers or a stroll to nearby Wylder Hotel, Eastwind, or Union + Post for a drink or cozy atmosphere.brbrbrbrOutdoor lovers can hike the trails at Elm Ridge Wild Forest or gear up at Windham Mountain Outfitters before hitting the slopes at Windham Mountain Club.brbrbrbrArt and culture thrive here, explore local talent at Windham Fine Arts, then browse the shelves at Briars & Brambles Books or pick up luxury clothing and home goods at Gardenheir.brbrbrbrFor relaxation, unwind at The Windham Spa, and when evening rolls around, enjoy wood-fired dishes at Millrock Restaurant or live music at The Windham Local.brbrbrbrWhether you're here to adventure, relax, or simply take in the charm of Windham, Carrotflower Farmhouse is your perfect base.brbrbrbrGetting Around:brbrCarrotflower Farmhouse is just 2.5 hours from New York City. A car is essential for getting there and exploring the area. The main access routes are the I-87 S, NJ-17 S and Taconic State Pkwy. We strongly recommend a 4x4 or a car with four-wheel drive, especially in winter, to handle snow and gravel roads.

Carrotflower Farmhouse: Ski Views | Walk to Town

Windham, New York, United States

Bed

Bath

Sleeps

$253.8

Unwind in this serene, inviting condo, a haven for year-round relaxation. Experience the natural splendor of the Catskills region, renowned for its laid-back, trendy small-town vibe and abundant recreational offerings. This recently revitalized residence, adorned with cheerful decor, is conveniently located mere minutes from Windham Mountain and steps away from the enchanting Windham Path. Immerse yourself in nature's beauty, captivating vistas, adventures and the charming town.

Condo

All-Season Condo - Ski Windham l Hunter l Pool l Hike l Fish

Windham, New York, United States

Bed

Bath

Sleeps

$807.24

A spectacular open floor plan with a gas fireplace and grand dining room. The entryway has a custom wet bar with wine fridge and sink . Grand open floor plan with vaulted ceiling in Living room and dining room , lower floor has a big screen tv along with a foosball table and a mud room entrance for ski storage and a separate bar area /seating area for a relaxing cocktail before enjoying a steam shower or a wonderful experience in a custom cedar steam room/ sauna. For your outdoor experience enjoy a 8 person hot tub as well as a outdoor wood burning fire pit.

Stunning Chalet style home with 8 Person Hot Tub, Fire pit & Sauna & steam rm.

Windham, New York, United States

Bed

Bath

Sleeps

$550.8

Perfect mountain getaway for all seasons! Skiing, hiking, biking, golfing, fishing or just relaxing! Enjoy the best of the catskills in this updated contemporary on over 25 acres with breathtaking views. Just minutes to town and Windham Mt ski area. Unwind and rejuvenate with all amenities for work and play.

5 min to Windham, 15 min to Hunter, 40 min to Belleayre and Plattekill!

Windham, New York, United States

Bed

Bath

10

Sleeps

$1334.57

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

New Custom Built Catskill Mountain Chalet with Elevator

Windham, New York, United States

Bed

Bath

Sleeps

$598.49

Summary:brbrWelcome to 27 Church St, a rustic and cozy mountain home just 3 minutes from Windham Mountain and downtown Windham’s charming shops and restaurants. Perfect for families, groups, and ski goers, this spacious 5-bedroom, 3-bath retreat blends modern comfort with classic cabin warmth, creating the ideal Catskills escape.brbrbrbrInside, you’ll find two fully equipped modern kitchens—perfect for group cooking or multi-family stays. The open living spaces feature a wood stove, comfortable seating, and large windows that let in natural light and offer peaceful views of the surrounding creek and forest. Whether you’re relaxing with a morning coffee or unwinding after a day on the slopes, every corner feels like home.brbrbrbrStep outside to enjoy the private hot tub, where you can soak under the stars while listening to the gentle sounds of the nearby stream. Fire up the grill for a group barbecue, or gather around the wood stove for cozy evenings in.brbrbrbrLocated just minutes from Windham and Hunter Mountains, you’ll have easy access to skiing, hiking, and outdoor adventures year-round. Explore scenic trails, enjoy local wine bars, or discover nearby restaurants and shops.brbrWith its hot tub, wood stove, and creekside charm, 27 Church St offers the perfect mix of comfort, convenience, and natural beauty—a true Catskills getaway for those seeking peace and adventure.brbrbrbrEscape to 27 Church St, a cozy 5-bedroom retreat just 3 minutes from Windham Mountain. Featuring two modern kitchens, a hot tub, wood stove, and serene creek views, this home is perfect for families, groups, and ski goers. Enjoy nearby hiking, wine bars, and restaurants, then unwind in comfort surrounded by rustic charm. Whether you’re planning a ski weekend or a peaceful getaway, this inviting home offers the ideal Catskills experience—modern amenities meets mountain tranquility.brbrbrbrGetting Around:brbrLess than a minute drive to Windham Mountain and many local restaurants and shops in townbrbrbrbrOther Things to Note:brbr** As most of the homes are on wells, there can be a slight sulfur or iron smell to the water. It is safe to use and consume, but bottled water is recommended if you're sensitive to that ***brbrbrbrInteraction with Guests:brbrI like to allow guests the freedom to explore the home and all of its amenities at their own pace. I went through great lengths to enter all of the information that you could need into the listing so please feel free to review it if you have any questions as to anything that the home has to offer. However, if you run into any emergencies regarding the home (for example: a drain gets clogged or an item is accidentally damaged) please feel free to reach out to me.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..

Rustic Retreat | Hot Tub & 3 Mins to Windham Mtn

Windham, New York, United States

Bed

Bath

Sleeps

$199.8

Cozy, restored 1922 Caboose for rent in the center of downtown Windham...walking distance to restaurants, bars, shops, bus station...1/2 mile to Windham Ski Mountain...located on property of Triplex Movie theatre, Subway & Carvel shops, Game Room, Laundromat..caboose has queen size bed, TV, Wifi, Microwave, refrigerator, air conditioning, ample parking...A unique, historical overnight experience!!

Apartment

Cozy Caboose in the city

Windham, New York, United States

Bed

Bath

Sleeps

$558.0

Your Windham adventure begins at this wonderful 4-bedroom cottage. Inside, guests find a cozy mix of beds including a king, queen, twin, and full, plus a living room with an extra queen bed for added comfort. Three bathrooms with refreshing showers make getting ready a breeze. The space stays pleasant year-round with heating and AC. Whether you’re gathering in the living room or unwinding in your private bedroom, this cottage offers an amazing retreat. Kick back, relax, and enjoy everything Windham and our Aframe has to offer.

Cottage

A-Frame 4-bedroom cottage with AC in charming Windham

Windham, New York, United States

Bed

Bath

Sleeps

$364.36

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..

Secluded Cabin with Hot Tub 5 Min to Windham Mtn

Windham, New York, United States

Bed

Bath

Sleeps

$1007.1

Welcome to a wonderful oasis of tranquility. Beautiful bright A-frame home sited on 10 secluded private acres with open meadows, woods, and running brook. Dramatic views of Catskill Mt range and ski trails of Windham. Tastefully decorated 4 bedrooms, 2 bath with open kitchen and great living area with a studio loft. Great family vacation retreat with fast WiFi only 2.15h away from the NYC. 3 miles to Windham and it’s restaurants and cafes. Lots of hiking, scenic biking, golfing attractions.

HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views

Windham, New York, United States

Bed

Bath

Sleeps

$301.32

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.

Windham Family Getaway

Windham, New York, United States

3

Bed

Bath

9

Sleeps

$360.05

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

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

Windham, New York, United States

3

Bed

Bath

Sleeps

$586.44

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

Cabin

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

Windham, New York, United States

Bed

Bath

Sleeps

$241.95

True mountain getaway, just 2.5 hours from NYC!! brModern and clean 2 bedroom 2 bathroom townhouse minutes to Windham Mountain. Enjoy beautiful wood-burning fireplace, Roku TV and high speed Wi-Fi perfect for remote work. Amenities include outdoor pool (open from Memorial through Labor Day), pickleball, basketball and tennis courts, as well as a fire pit with Adirondack chairs. Very close to town and the amazing escarpment hiking and Elm Ridge mountain bike trails. NOW OPEN FOR 2024/25 SKI SEASON!!brbrThe spacebrbrThis is a spacious two bedroom, two bathroom condo, with a fully-stocked kitchen and a living room with fireplace. Full kitchen, oven & stove-top, fridge, microwave, coffee maker and dishwasher. There is a large private back deck to enjoy the outdoors.brThe spacious master bedroom has a comfortable queen size bed. The second bedroom has twin over full bunk beds and a separate twin bed. There are two full baths, one on each floor.brRelax in our living room on the new comfy couch which faces the wood-burning fireplace. The living room also features a flat screen TV with Roku and Wi-Fi. A roaring fire will keep you warm even on the coldest nights. brbrThe condo has A/C for the summer months. There is also a tower fan in each bedroom.brbrThe condo comes fully stocked with all the essentials you need to have your ultimate mountain escape! Towels, linens and toiletries are provided. Ideal for 6 people to enjoy.brbrGuest accessbrbrYou will have access to the whole condo including all of the complex amenities: laundry in complex (different building), outdoor pool and two tennis courts.brbrInteraction with guestsbrbrWe will be available via phone/text in case you run into any problems during your stay. There is a property manager on site in the event there s a problem.brbrOther things to notebrbrEarly bird check-in (9 am) and Twilight check-out (5 pm) are available for a fee. Subject to availability.brbrBring your firewood with you or pick it up in Hickory Hill Market down the road or gas station nearby.brbrThere are security cameras located above the front door overlooking the parking lot to ensure safety of our guests. It does not look into any interior spaces.

Redwood Retreat in Windham - minutes to Mtn!

Windham, New York, United States

Bed

Bath