Vacation Home Rentals By Owner In Windham, NY

Get ready to relax in this 3-bedroom condo in the Enclave Club at Windham. With 2 king beds and 2 bunk beds, guests will have plenty of space to unwind and relax around the fire after a day of skiing. Located directly at the base of the ski run with easy access to the lodge and slopes. Enjoy the on-site outdoor pool, fire pit, hot-tubs, exercise room, game room or gather with friends in the warm common areas. Please reach out if interested.

Condo

Luxury 3-BR Enclave condo in Windham, ski-in/ski-out with pool and hot-tub

Windham, New York, United States

3

Bed

3

Bath

8

Sleeps

$777.14

Newly renovated quiet luxury retreat, close to town, the slopes, golf and hiking.brThe best skiing, riding and hiking in NY is just minutes away - 10 minutes to Windham Mountain and 23 minutes to Hunter. brOur home has all the amenities you need for the perfect Catskills getaway with family and friends: 5 bedrooms, 3 baths, fully-stocked entertainment kitchen, 2 living rooms, smart TVs, reading room, workspaces, grill, bluestone patio and fire-pit.brLOCATION:brOur luxurious modern mountain retreat is an 8 minute drive from the restaurants and shops in quaint Windham Center, 10 minutes from Windham Mountain, 23 minutes to Hunter Mountain and just steps from Windham Manor.brbrSet back in the trees, our home is on 5.5 acres of private land with a sprawling front yard, new bluestone patio with outdoor dining and fire pit (birds and the rustling of leaves will be the only sounds you hear). brbrFor breakfast, stock up on fresh eggs from our neighbors down the road (and while you are there, say hello to their friendly pet goats!), or take a quick drive to town and take your pick of local eateries. brbrOur entertainment kitchen is fully equipped with new appliances, all the kitchenware you'll need and a large island for all of your cooking needs. If you aren't in the mood to cook (or gill), hop over to any of Windham, Hunter or Tannersville for a bite (or, if you are feeling particularly adventurous, visit Kingston, Saugerties or Woodstock for many more restaurant options). Renowned for its skiing and snowboarding in the winter, this corner of Greene County is also famous for its beautiful hiking, biking, lakes and swimming holes. brbrWE CANNOT HOST PETS.brbrMAXIMUM GUESTS - 12 (additional charge for more than 10 guests)brbrWE CANNOT HAVE PARTIES. We strictly observe Airbnb's global party ban policy.brbrSURVEILLANCE CAMERAS:brPlease read details in the Other Details To Note section below.brbrAIR CONDITIONING:brThe main level of the house is equipped with central air. The bedrooms do not have A/C. All the bedrooms except the bunk room are equipped with ceiling fans. Electric fans are provided in the bunk room for your comfort.brbrHIGH SPEED INTERNET:brUnlike most homes in the area that rely on slow satellite internet, we have newly installed high speed broadband making work-from-home and streaming your favorite shows and movies a breeze.brbrCOMFORT AND SPACE FOR ALL OUR GUESTS:brChoose from three separate spacious sitting areas or try them all and pick your favorite! Watch a movie together in the spacious living room in front of a wood-burning fireplace or let the kids hang out in the cozy den. brbrKITCHEN:brFully stocked modern kitchen with new stainless appliances and a large island that is the ideal place for a glass of wine before dinner.brAppliances include:brInduction stovetopbrMicrowavebrDishwasherbrCoffee MakerbrElectric KettlebrRefrigerator with filtered water supply and ice makerbrToaster ovenbrSeparate beverage/wine fridgebrbrBEDROOMS:brThree on the second level and two on main level.brFour of the bedrooms have king beds (with memory foam mattresses) andbrthe fifth bunk room (on the second level) has built-in Twin XL bunk beds (sleeps 4), each equipped with built-in reading light and USB charger.brbrNO PERSONAL PILLOWS, SHEETS OR OTHER BEDDING ALLOWED. brTo avoid cross contamination and potential spread of bed bugs we do not allow guests to bring pillows and sheets/blankets to our home. We keep our home very clean and follow sanitizing procedures when it comes to laundry and general cleaning between guests. We also replace bedding frequently to make sure it is always in good condition.

Birch Hill - Luxury Mountain Retreat

Windham, New York, United States

Bed

Bath

Sleeps

$309.81

About this spacebrSpacious 3-Bedroom Townhouse with Sleeping Loft and Wood-Burning Fireplace at Windham Ski Mountain, Minutes away from the Windham Village and offering a privat shuttle to the slopes.brbrNestled amidst the picturesque beauty of Windham Ski Mountain, this charming 3-bedroom townhouse offers the perfect blend of rustic charm and modern comfort. With 2 bathrooms, a wood-burning fireplace, and privat patio, this is the quintessential mountain retreat for families and snow enthusiasts alike.brbrThe spacebrWelcome to our Private Townhouse at Crystal Pond Unit! This spacious 3-bedroom, two-bath retreat is the perfect getaway in Windham, New York.brbrAs you enter the ground floor, you'll be greeted by an open living and dining area, complemented by a cozy wood-burning fireplace. The kitchen boasts extra counter seating, ideal for casual meals or simply enjoying a morning coffee. A tiled mudroom entry keeps things organized and practical.brbrStep through sliding doors to your private deck, where you can relax while overlooking a serene pond. The main floor is completed by a full bath and laundry facilities for your convenience.brbrUpstairs, you'll find two roomy bedrooms and another full bath, ensuring comfort and privacy for all. But the real bonus is the 3rd-level loft, perfect for additional sleeping space or as a den/playroom. Master Bdr : Queen, Second Bdr Full, Loft 2 Twin beds (upon request additional Blow up Mattresses are available to accommodate an additional 2 people).brbrOur location offers easy in-and-out access, and Crystal Pond has a summer pool for relaxation. In the winter, enjoy the hassle-free weekend shuttle to Windham Mountain on the half hour, saving you the trouble of finding parking. We're just 3 minutes from Windham town and 5 min from Windham ski mountain, 15-20 minutes away from Hunter Mountain, as well as nearby cross country, hiking and bike trails. brbrWhether you're seeking adventure or relaxation, our Crystal Pond townhouse is your ideal base in the Catskills. Book your stay today and experience all that this beautiful area has to offer!brbrOther things to notebrWelcome to our townhouse, where your comfort and convenience are our top priorities. We understand that the little things can make a big difference when it comes to your comfort. That's why we provide a selection of basic amenities to ensure your arrival is smooth and stress-free.brbrUpon stepping into our townhouse, you'll discover a home-away-from-home experience that begins with complimentary hotel-sized shampoo, conditioner, and shower gel. Freshen up after your journey and start your stay feeling rejuvenated and pampered. To get you going, we provide ground Coffee, Olive Oil, basic kitchen essentials, spices, sugar as well as fire wood to get you cozy after a day of skiing.brbrWe are here to make your stay as enjoyable as possible. brOur Property Manager Sue Shaw is at your disposal for any questions or needs.brConcierge Services available upon request (private chef, massage, private ski lessons, private yoga classes and more)brbrAt Windham17 townhouse, your comfort and relaxation are our utmost priorities. We look forward to hosting you and providing a welcoming atmosphere where you can unwind and create lasting memories. Enjoy your stay!

Spacious Townhouse minutes from Village and Slopes with shuttle to mountain

Windham, New York, United States

Bed

Bath

Sleeps

$669.6

Highest-rated superhost Airbnb- new to VRBO! brEscape to Nature in All Four Seasons at this beautifully renovated 1900s farmhouse. Nestled on 5 private acres and just one mile from Windham Mountain Ski Resort and a short stroll down to Main Street! Surrounded by 46 acres of permanently preserved NY State land, this retreat offers unparalleled privacy and tranquility. Whether you're planning a family getaway, a wedding weekend, a ski trip, or an escape with friends, this spacious and artfully curated home offers the perfect blend of rustic charm and modern comfort.brbrbrbrThe Farmhouse ExperiencebrSpacious Accommodations: Five uniquely appointed bedrooms plus a cozy 'bunk cove' designed for kids or additional guests.brbrGourmet Country Kitchen: A large eat-in kitchen equipped with a dedicated coffee bar and libation station, perfect for communal gatherings.brbrArtistic Touches: Original artwork adorns the interiors, adding a unique and personal flair.brbrModern Amenities: Laptop-friendly workspaces with ample plugs and chargers to keep you connected.brbrbrbrOutdoor DelightsbrWraparound Porch: Enjoy morning coffee or evening cocktails with serene views.brbrFirepit Gatherings: A 12-person firepit area ideal for storytelling and s'mores under the stars.brbrBarbecue Ready: All season outdoor grill for cookouts anytime.brbrToboggan Hill: A gentle slope perfect for children's sledding adventures during snowy days!brbrEnjoy our residing large family of deer at dusk and dawn!brbrbrbrbrAprès all day at Windham Mountain ResortbrWindham Mountain Resort remains accessible to the public, offering a range of winter activities:brbrSkiing and Snowboarding: Enjoy 285 acres of terrain suitable for all skill levels.brbrSnow Tubing: Family-friendly fun with dedicated lanes.brbrLessons and Rentals: Available for beginners and those looking to refine their skills.brbrDining Options: A variety of on-mountain restaurants to satisfy your après-ski cravings.brbrbrbrbrExplore WindhambrJust a short walk from the farmhouse, Main Street Windham offers:brbrPubs and Taverns: Take your pick of many fabulous local eateries, all of which are detailed in the house.brbrBoutique Shopping: Discover unique gifts, artisanal goods, and local crafts.brbrArt Galleries: Explore works by regional artists.brbrCafés and Bakeries: Enjoy freshly brewed coffee, local bites, and homemade pastries.brbrLocal Favorite for Family Fun-Chicken Run: known for its comfort food, live music, line dancing, volleyball, giant outdoor firepit and dining options all next to an idyllic, flowing river. brbrbrbrbrSafety and ConveniencebrSecurity Measures: Equipped with exterior cameras and motion detector lights.brbrWeather Preparedness: Driveway plowed after snowfalls of three inches or more.brbrFire Safety: Carbon monoxide detectors outside every room and common areas, smoke detectors throughout, and fire extinguishers in key locations.brbrParking: Private and dedicated parking areas for guests, up to 6 vehicles.brbrbrbrWhether you're seeking adventure, relaxation, or a bit of both, our farmhouse offers an idyllic retreat for all ages and occasions. Experience the charm, allure, and adventure of Windham in every season at our farmhouse retreat. Your perfect getaway awaits!

Country House

THE PAINTED COW- 5 acre farm, walk to Mainstreet, 1 mile to slopes in Windham!!

Windham, New York, United States

Bed

Bath

Sleeps

$317.14

Unwind in Windham at this charming townhome. With two bedrooms featuring a king bed, two trundle , and a twin over queen bunk bed, there’s plenty of space for everyone. The two bathrooms offer both a shower and a bathtub, perfect for relaxing after a day of adventure. Guests will appreciate the charming hot tub with forest view on a private deck, cozy heating and a wood burning fireplace thoughtful touches like an iron and hair dryer, luxurious bathroom amenities, coffee and tea station, popcorn machine, 2 new TVS, games, guitar, exercise tools and many more . Bright and inviting, this fantastic townhome provides a comfortable retreat for your getaway. Personalized welcome packages ! This is a unique unit being the larger in the complex that offers functional large hot tub, extra closets, new functional furniture and newly renovated kitchen and appliances great place to call home base while you're away, We hope you enjoy your stay.

Exceptional townhome with hot tub & fireplace and customize stays in Windham

Windham, New York, United States

Bed

Bath

Sleeps

$211.5

Steps from the Mountain! Just 1 mile away with a crisp mountain view, our beautiful chalet is a mere 5 minute drive from the slopes of Windham and just 15 minutes from Hunter!brbrbrbrA short walk or drive from the charming town of Windham, the cute mountain town itself has many great shops, restaurants and activities all within a short drive. Or just relax by the fire or with a view of the mountain from the hot tub (Winter only, tub is not active during the summer).brbrbrbrTake the entire 2nd floor apartment of our wonderful chalet, a beautiful and sizable living space with a Smart TV (with Netflix, Prime and more) and a beautiful log fireplace, 2 full bedrooms, 2 full bathrooms (one en suite) and a full kitchen - everything you need for a stress free vacation. brbrbrbrWhen you arrive, we will make sure there is coffee and tea in the kitchen and if you have any special requests, simply let us know and we'll do what we can to make them happen.brbrbrbrThere is a large garden that's just perfect to play some catch or build snowmen together with an unbridled view of the Windham ski area.brbrbrbrThere is a washer and dryer on the premises (ask us if you want to use), one car garage and private driveway. Sofas are not sleepers but could comfortably take an additional adult.brbrbrbrYou are welcome to park in the garage if it is not in use.brbrbrbrFurry Friends are welcome for an additional fee.brbrbrbrYou have access to the entire first floor and garden. Garage is available for skis/snowboards.brbrbrbrIf we are not there you are welcome to use the garage.brbrbrbrWe will be available by email/phone if you have any questions and our property manager near by for anything urgent when we are not there.brbrbrbrThe historic town of Windham is an all season getaway. Known as the 'Gem of the Catskills', Windham is filled with exceptional eateries, speciality shops and is just moments away from a fantastic amount of both winter and summer activities, and just a short drive away from some of the most charming Hamlets New York has to offer.brbrbrbrYou have a huge variety of hikes available, though you will need a car if you're planning on going out of the town itself.brbrbrbrHot tub is not active during the summer months

Apartment

Mountain view apartment, 5mins to Ski Area!

Windham, New York, United States

Bed

Bath

Sleeps

$132.23

Steps from the Mountain! Just 1 mile away with a crisp mountain view, our beautiful chalet is a mere 5 minute drive from the slopes of Windham and just 15 minutes from Hunter!brbrbrbrA short walk or drive from the charming town of Windham, you're perfectly located for a winter getaway. The town itself is a wonderful mountain community with many great shops, restaurants and activities all within a short drive.brbrbrbrTake the entire 1st floor of our wonderful chalet, a beautiful and sizable living space with Smart TV (with Netflix, Prime and more) and a beautiful electric fireplace, a full bedroom, full bathroom. We’ve just installed a small full kitchen and you are just minutes from the town's excellent and numerous bars and eateries. There is a mini fridge at the base of the water cooler too.brbrbrbrIf you have any special requests, simply let us know and we'll do what we can to make them happen.brbrbrbrThere is a large garden that's just perfect to play some catch or build snowmen together with an unbridled view of the Windham ski area.brbrbrbrThere is a washer dryer on the premises (let us know if you wish to use and we will arrange access to the utility room) and private driveway. You are welcome to park in the garage if it is not in use.brbrbrbrFurry Friends are welcome for an additional fee.brbrbrbrYou have access to the entire first floor and garden. Garage is available for skis/snowboards.brbrbrbrIf we are not there you are welcome to use the garage.brbrbrbrWe will be available by email/phone if you have any questions and our property manager near by for anything urgent when we are not there. Otherwise if we are in the upstairs unit and more than happy to help!brbrbrbrThe historic town of Windham is an all season getaway. Known as the 'Gem of the Catskills', Windham is filled with exceptional eateries, speciality shops and is just moments away from a fantastic amount of both winter and summer activities, and just a short drive away from some of the most charming Hamlets New York has to offer.brbrbrbrYou have a huge variety of hikes available, though you will need a car if you're planning on going out of the town itself.

Cozy Cabin Condo by the Mountain, 5mins to skiing!

Windham, New York, United States

Bed

Bath

Sleeps

$275.34

pSteps from the Mountain! Just 1 mile away with a crisp mountain view, our beautiful chalet is a mere 5 minute drive from the slopes of Windham and just 15 minutes from Hunter!/pbrbrpA short walk or drive from the charming town of Windham, you're perfectly located for a winter getaway. The town itself is a wonderful mountain community with many great shops, restaurants and activities all within a short drive. Or just relax by the fire or with a view of the mountain from the hot tub (hot tub only active in Winter)./pbrbrpSplit level, 2 beautiful and sizeable living spaces - both with large smart TVs (with Netflix, Prime and more) and fireplaces (one real, one electric), 3 full bedrooms, 3 full bathrooms (one ensuite, one upstairs, one down), and a fully equipped kitchen - everything you need for a stress free vacation. /pbrbrpThere is an additional pullout couch downstairs/pbrbrpWhen you arrive, we will make sure there is coffee and tea in the kitchen and if you have any special requests, simply let us know and we'll do what we can to make them happen./pbrbrpThere is a large garden that's just perfect to play some catch or build snowmen together with an unbridled view of the Windham ski area./pbrbrpThere is a washer and dryer on the premises (ask us if you want to use), one car garage and private driveway./pbrbrpFurry Friends are welcome for an additional fee./pbrbrpYou will have access to the full chalet, garage and grounds. Please let us know if you wish to use the washer and/or dryer and we can arrange access to the utility room./pbrbrpWe will be available by email if you have any questions and our property manager near by for anything urgent./pbrbrpThe historic town of Windham is an all season getaway. Known as the 'Gem of the Catskills', Windham is filled with exceptional eateries, speciality shops and is just moments away from a fantastic amount of both winter and summer activities, and just a short drive away from some of the most charming Hamlets New York has to offer./pbrbrpYou have a huge variety of hikes available, though you will need a car if you're planning on going out of the town itself./p

Chalet

Rustic Mountain view Cabin 5 mins to Ski Area!

Windham, New York, United States

Bed

Bath

Sleeps

$820.78

Witness the breathtaking beauty of the Catskill Mountains at this stunning 6-bed, 5.5-bath vacation rental. Nestled in nature, this expansive estate is the perfect retreat for outdoor enthusiasts. Indulge in the warmth of the fireplaces, unwind on the deck with spectacular views, or sizzle up a feast on the gas grill. Boasting a secluded duality while being near attractions, this gem is near hiking trails, ski slopes, and other hot spots in town.brbr-- THE PROPERTY --brbrBuilt in October 2023 | Gas Grill (Propane Provided) | Radiant Heated Floors | Home Office w/ Laptop-Friendly Desk, Monitor & Printer brbrBedroom 1 (Suite): King Bed | Bedroom 2 (Suite): Queen Bed | Bedroom 3 (Suite): Queen Bed | Bedroom 4 (Suite): Queen Bed | Bedroom 5: Queen Bed | Bedroom 6: Queen Bed | Additional Sleeping: Pack ‘n PlaybrbrOUTDOOR LIVING: Mountain view, 5 private acres of landbrINDOOR LIVING: 4 Smart TVs, 2 linear gas fireplaces, 2 ceiling fans, central A/C & heat, 2 living room spaces, board gamesbrCHEF’S KITCHEN: Well-equipped w/ Viking appliances, fridge, 8-burner stove, double oven, 24 dishwashers (2), microwave, toaster oven, coffee bar w/ Nespresso coffee maker, drip coffee maker, blender, waffle maker, cooking basics, dishware & flatware, trash bags, paper towels, wine fridge, porcelain countertops, Leicht brandbrKITCHENETTE: Microwave, 24 dishwasher, ice maker and wine fridge, Leicht brandbrGENERAL: Free WiFi, washer & dryer, laundry detergent, iron & board, hair dryer, towels & linens, hangers, optional housekeeping, snow removal included brFAQ: 5 exterior security cameras (facing out)brACCESSIBILITY: 3-story home, 5 stairs to enter, bedroom & baths on main floor, stairs to addt’l bedrooms on upper & lower levels brPARKING: Garage (2 vehicles), gravel driveway (2 vehicles), Tesla EV charger (compatible w/ other electric vehicles)brbr-- THE LOCATION --brbrSKI ALL DAY: Windham Mountain Club (2 miles), Hunter Mountain Resort (10 miles)brOUTDOOR BEAUTY: Five State Lookout (6 miles), Mountain Top Arboretum (10 miles), Kaaterskill Wild Forest (16 miles), Mine Kill State Park (24 miles) brFAMILY ACTIVITIES: Zoom Flume Water Park (10 miles), Thomas Cole National Historic Site (23 miles)brAIRPORT: Albany International Airport (62 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 smoking br- No pets allowedbr- No events, parties, or large gatherings br- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This 3-story property requires 5 stairs to enter. While it offers a bedroom and 1.5 bathrooms on the main level, additional interior stairs are required to access all of the bedrooms located on the upper and lower levelsbr- NOTE: Your safety matters. This property features 5 exterior security cameras. Camera 1 is a Ring doorbell device with an exterior security camera facing the front outdoor entry. Camera 2 is a floodlight above the main garage, facing the driveway. Camera 3 is inside the main garage, facing the garage door. Camera 4 is above the back garage, facing the driveway. Camera 5 is inside the back garage, facing the garage door. Cameras 3 and 5 continuously livestream video and sound. Cameras 1, 2, and 4 actively record video and sound when motion is detected by the devices (including devices linked to the cameras such as the alarm system’s motion detector) or when the video doorbell button is pressed

Cabin

Brand New Luxury Ski Cabin - 2 Mi to Windham Mtn!

Windham, New York, United States

Bed

Bath

Sleeps

$286.93

Summary:brbrEnjoy a perfect blend of comfort, convenience, and mountain charm at this modern 2-bedroom, 2-bath home just 1 minute from Windham Mountain. Designed for up to 7 guests, this cozy getaway is ideal for families, groups, and ski enthusiasts seeking a stylish space close to the slopes and local attractions.brbrbrbrAfter a day of skiing or hiking, unwind in the private hot tub or gather around the outdoor fire pit under a blanket of stars. Inside, you’ll find a warm and inviting open-concept living area, complete with modern finishes, plush furnishings, and plenty of natural light. The fully equipped kitchen and dining area make it easy to cook, share meals, and reconnect after a day of adventure.brbrbrbrLocated within walking distance to town and local restaurants, and just a short drive to Windham Path, this home offers unbeatable access to all the best the Catskills have to offer. Spend the day exploring Hunter Mountain, nearby trails, or the charming Windham Wine Bar, then come home to comfort and relaxation in your own private retreat.brbrbrbrWhether you’re here for a ski trip, romantic weekend, or family getaway, this Windham hideaway provides the perfect balance of proximity, privacy, and modern luxury.brbrbrbrStay just 1 minute from Windham Mountain in this modern 2BR/2BA home featuring a hot tub, fire pit, and cozy open layout. Walk to local restaurants or drive 15 minutes to Hunter Mountain for more adventure. Perfect for families, friends, or ski lovers, this stylish getaway offers modern comfort and mountain charm — your ideal Catskills retreat for every season.brbrbrbrThe Space:brbrNewly renovated two bedroom home, each with king beds and ensuite baths located in the heart of the Catskills. Large furnished outdoor patio with hot tub. Fireplace and fire pit. Close proximity to hiking, skiing, kids activities, and everything local in the area. Enjoy as birds will visit you while you sip your morning coffee.brbrbrbrBeautiful view of the foliage with a river in your backyard!brbrbrbrClose to:brbrbrbrWindham Mountain: .3 miles brbrWin Country Club: 1.1 miles brbrWylder Lodge: 1.3 miles brbrEastWind Lodge: 1.3 miles brbrThe Windham Path: 1.5 miles brbrHunter Mountain: 10 miles brbrbrbrAcross the street:brbrbrbrZe Windham Wine Bar brbrMillrock Restaurant brbrLa Patisserie Normande brbrWindham Pizzaria brbrMovie Theater brbrThe Tap RoombrbrWindham Local (coffee) brbrCarvelbrbrSubway brbrWindham DinnerbrbrbrbrGuest Access:brbrGuests have access to an acre of the yard and stream as well as all parts to the house except the utility closetbrbrbrbrOther 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..

Modern Windham Retreat w/ Hot Tub & Fire Pit

Windham, New York, United States

Bed

Bath

7

Sleeps

$786.86

Recently renovated 4-bedroom house with views of the trails on Windham Mountain from 3 of the 4 bedrooms. Ski Windham during the day (a 2-minute drive) and unwind in the evening at one of the restaurants in town (walking distance) or stay home and enjoy the stars from the hot tub. brbrThere are two living rooms. One on the mail level and a second on the lower level with games and arcade for the kids.

Ski retreat with views of Windham, in heart of town near all.

Windham, New York, United States

5

Bed

Bath

13

Sleeps

$709.57

Welcome to our 2 bedroom, 2 bath, ski-in/ski-out condo, located at the base of Windham Mountain! This getaway holds 2 cozy bedrooms, each with resort-style bedding and unsurpassed comfort. The wonderfully appointed master offers a lavish queen-sized bed and comes with an en-suite bathroom that includes a refreshing steam shower. The other room holds 2 sets of bunk beds, with an attached bath. Building amenities include pool, hot tubs, gym, ski lockers, heated indoor parking and common lounges.

Condo

2 Bed Ski-In/Out Condo

Windham, New York, United States

Bed

Bath

6

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

$864.0

Welcome to our beautiful, cozy mountain retreat! Our beautiful and spacious home is brand new and completely renovated. It is perfect for your next getaway. Whether you’re planning a bachelor or bachlorette party, a family ski trip, a leaf-peeping adventure, or a weekend away with friends, this home has everything you need for a comfortable and enjoyable stay.brbrOur home is ideally located minutes away from Windham Mountain. brbrBook now and experience the best of what the mountains have to offer and get ready for an unforgettable adventure!brWe take pride in providing exceptional service and ensuring our guests have a memorable stay, we are always close by and can accommodate any special request. brbrOur house is great for large families or multiple families traveling together. With five rooms for couples, a room with bunk beds and a queen bed perfect for kids, and plenty of space all around, it’s the perfect spot for your next winter vacation.brbrExperience a beautiful property attached to Union And Post hotel and Restaurant. The home comes with all the amenities of the hotel and the convenience of the restaurant. brbrThe house is fully equipped with 5 bedrooms and 3 bathrooms, a large kitchen, an open living room, and a large deck. brbrCan comfortably sleep up to 12 people, making it perfect for large family gatheringsbrbrFully stocked kitchen for those who like to cook or bakebrbrLaundry room with washer/dryer and ironing boardbrbrOnly 2 minutes from the golf course and downtown Windham, 5 minutes from Windham Ski Mountain, or 20 minutes from Hunter MountainbrbrFantastic hiking trails are located all around and many are within a 5-minute drivebrbrSummer activities include hiking, mountain biking, zip lining, and all of the outdoor activities you can imagine. br

BRAND NEW completely renovated house in Windham, 5 bed/ 3 bath

Windham, New York, United States

Bed

Bath

Sleeps

$275.4

brOur comfy home has 4 Bedrooms - 2 King size bedrooms, 2 Queen size Bedroom. One full bathroom upstairs and 1 full bathroom downstairs. New comforters and warm blankets. Downstairs entrance opens to a large mud room perfect for ski & boot storage. In addition to the mud room, downstairs has 3 bedrooms (2 Queen, 1 King) along with the full bathroom. Upstairs, a Master bedroom with enough room for pack 'n play or crib, a Full Kitchen, Comfortable Living room, with L shaped couch, Full Bath, Fireplace, YouTube TV, Apple TV, Roku, DVD, high speed WIFI, and landline with local & long distance. The kitchen has Microwave, Coffee Maker, Dishwasher, Toaster Oven, Phone, table settings for 10, Martini, Wine & Beer Glasses. Dining Area opens to the deck with Gas Grill & Picnic Table. brbrIncludes All Linens, Sheets & Towels and Extra Blankets in every closet. Washer & Dryer. Firewood Provided at no additional cost.brbrArt galleries, antiques, museums, concerts, cinema, 4 local golf courses, tennis, lakes, fishing, hunting, swimming, parks, hiking, biking, horseback riding, sightseeing, paint ball, downhill skiing, tubing park, water park, restaurants, ice skating rink and many summer and winter festivals.brbrbrKeywords: Ski area, private house, wooded area, near town, hiking, biking, water park, ice skating, swimming, fishing, tubing, antiques, wine, microbrew, summer festivals, World Cup Mountain Biking, BBQ, deck, relax enjoy warm days and cooler nights.brbr

Windham: Golf, Lakes, Nature, Farms & more all nearby!

Windham, New York, United States

4

Bed

Bath

8

Sleeps

$783.37

Wake up to direct ski slope views in this elevated Catskills chalet just minutes from Windham Mountain. Designed with vaulted ceilings, stone fireplace, and a warm vintage-meets-modern aesthetic, this 7BR retreat blends luxury with laid-back mountain charm. brbrUnwind in the hot tub or cedar sauna, enjoy fireside evenings on the wrap-around deck, or host epic game nights with air hockey, arcade games, and karaoke - this chalet is perfect for ski trips, group getaways, and all-season adventures.brbr⛰️ PROPERTY HIGHLIGHTS ⛰️br Prime location near Windham Ski Resort, Hunter Mountain & Catskills attractionsbr Huge game room with air hockey, arcade games, poker table, karaoke & board gamesbr Cozy living room with vaulted ceilings, wood-paneled walls, stacked stone gas fireplace, and slope viewsbr Private 6-person hot tub and cedar sauna with mountain viewsbr☕ Oversized wrap-around deck with rocking chairs, fire pit table, outdoor dining & grillbr Spacious yard with outdoor games br Fire pit with seating for 8 and string lights for ambiancebr High-speed WiFi throughoutbr Parking for multiple vehiclesbrbr*** Guest must be 23 years or older to book the property.br*** If you plan to bring pets please let us know in advance, pet fee required.br*** We recommend 4-wheel drive cars during snowy weather.brbr ️ LIVING ROOM ️br✔ Stacked stone gas fireplace with floor-to-ceiling windows showcasing mountain and slope viewsbr✔ Smart TV for streaming and entertainmentbr✔ Cozy velvet sofas seating the group comfortablybr✔ Additional lounge seating and a reading nook with comfy armchairbr✔ Warm vintage-meets-modern décor with woven rugs and Catskills characterbrbr KITCHEN & DINING br✔ Fully equipped eat-in kitchen with electric stove, oven, microwave, air-fry & dishwasherbr✔ Spacious countertops with essential cookware and serving piecesbr✔ Extendable farmhouse-style dining table seating up to 10br✔ Breakfast bar with stoolsbr☕ Espresso & tea station fully stockedbr✔ High chair and children’s dinnerware for family-friendly conveniencebrbr DECK (MAIN LEVEL) OUTDOOR DINING br✔ Farmhouse outdoor dining table seating 8br✔ Additional bar-height table for sunset cocktailsbr✔ High-end 4-burner gas grillbr✔ Rocking chairs, lounge seating, and cozy mountain ambiancebr Patio seating with firepit table, perfect for s’moresbrbr GAME ROOM br✔ Full-size air hockey tablebr✔ Ping pong table (conversion topper)br✔ Full-size arcade games including Fast & The Furious, Pac-Man & NBA Jam Deluxebr✔ Poker table and selection of board gamesbr✔ Brand-new karaoke machinebr✔ 75” wall-mounted TV and popcorn cart for movie nightsbrbr OUTDOOR ACTIVITIES br✔ Giant Connect Fourbr✔ Giant Jengabr✔ Cornhole & toss gamesbr✔ Giant Kick Dartsbrbr FIRE PIT br✔ Adirondack chairs for 8br✔ Bistro string lights for warm nighttime ambiancebr Ideal for s’mores, stargazing, and evening conversationsbrbr♨️ OUTDOOR HOT TUB & SAUNA AREA ♨️br✔ 6-person hot tub (open year-round)br✔ Cedar sauna with breathtaking mountain viewsbr✔ Ambient lighting for evening relaxationbr The perfect après-ski wellness retreatbrbr ️ BEDROOMS ️br✔ Bedroom 1 (First Floor): King bed with premium mattress, walk-in closet, deskbr✔ Bedroom 2 (Second Floor): King primary suite with en suite bathroom (shower/tub), ski slope views, walk-in closet, desk, 55” Smart TVbr✔ Bedroom 3 (Second Floor): Home office with pull-out queen sofa sleeperbr✔ Bedroom 4 (Basement): King bed + chaise twin bed, 55” TVbr✔ Bedroom 5 (Basement): King bed with closetbr✔ Bedroom 6 (Basement): Queen bed, desk, 55” TVbr✔ Bedroom 7 (Basement): Two bunk beds (2 queens + 2 twins), perfect for kids and steps from the game roombrbr KIDS PLAY ROOM br✔ Family-friendly games, books, and toysbr✔ Comfortable seating and play space near entertainment areasbr✔ Designed for fun, creativity, and easy supervisionbrbr PET POLICY brWe’re happy to welcome house-trained pets! There’s a $100 fee per pet (up to 2). if you plan to bring pets please make sure to let us know in advance. Any pet-related damage or excessive cleaning will be charged to the guest.brbr ️ NEARBY ATTRACTIONS ️br Windham Mountain Ski Resort – 2.6 miles (5 mins)br Hunter Mountain – 10.1 miles (17 mins)br Belleayre Mountain – ~45 minutesbr⛳ Windham House Golf Course – ~10 minutesbr☕ Windham Main Street (shops, cafés, movie theater) – 5 minutesbr Kaaterskill Falls & Viewing Platform – 30–35 minutesbr Hudson Amtrak Train Station – 35–40 minutesbr Local hiking trails, parks & seasonal events – nearbybr Breweries, restaurants & local markets – short drivebrbr◦ Rental agreement required after bookingbr◦ Quiet Hours / Noise Ordinance: The Town of Windham enforces quiet hours from 10:00 PM to 7:00 AM. Please be respectful of our neighbors. No outdoor music is permitted, and we kindly ask that doors remain closed to minimize noise.br◦ Pet Policy: Pets must be disclosed in advance; cleaning fee appliesbr◦ Smoking Policy: No smoking inside the home. Any evidence or odor of smoking will result in a $500 additional cleaning fee. Guests found violating this policy will be required to vacate the property immediately and without refund.br◦ Starter Supplies: Starter supplies provided (toiletries, detergent, dish soap, paper goods)br◦ Nearby grocery options: Hickory Hill Market (Windham) – grab-and-go sandwiches & pizza, 10 mins; Tops Friendly Market (Tannersville) – full-service supermarket, 22 minsbr◦ Wood fire pit available — please use firewood reasonably; excess use may incur a feebrHi. Please agree to the following rules.brbrI understand there is no smoking allowed in the cabin. There is a fine if there is any smell or evidence of smoking including vaping, tobacco, or water pipes inside the cabin.brbrI understand furniture should not be moved.brbrI understand there are no parties or events allowed. All visitors must be disclosed and approved by the host before the check in date.brbrI understand that a maximum of two pets (less than 25 lbs) are allowed per stay, subject to host approval. A $100 fee per pet per stay will be accessed prior to booking.brbrI understand that the renter must be at least 23 years old and must be present at the property for the entire stay.brbrGuests are responsible for their own safety and for using the property and amenities as intended. Please follow all house rules, posted warnings, and safety instructions. The host is not responsible for injuries resulting from misuse of the property, failure to follow rules, or voluntary risk-taking.

Chalet

Velvet Timber Haus | HotTub, Sauna, Firepit, Games

Windham, New York, United States

4

Bath

19

Sleeps

$1647.0

brAbout this spacebrbrThis spacious, serene and secluded chalet is a newly renovated seven bedroom five bathroom luxury property - 7 minutes from Windham and 15 minutes from Hunter ski resorts. Take a peaceful walk in our 6 acre forest, read by a roaring fire, relax in the spa bath, or prepare a gourmet meal in the chef’s kitchen w/ double oven, wet bar and coffee station. Second kitchen is great if you have multiple families renting. Or just preparing for the family. The gas fireplace is a great spot to watch a movie after a long day hiking or skiing. Roast marshmallows at the fire pit as you star gaze and a nightcap in the hot tub will melt all your worries away!brbrThe spacebrbrThis is a contemporary ski chalet, which has been inspired by the Japanese concept of Wabi- Sabi with a strong focus on organic materials, and a neutral color palet allowing guests to focus on the beauty of the natural and serene surroundings. A perfect way to get zen in nature without sparing any luxuries.brbrGuest accessbrbrThis property is on a private road 7 minutes from the town of Windham and can be accessed by car. Parking provided on plowed circular driveway.brbrOther things to notebrLooking for longer than just a weekend away Ask about longer stay discounts.

Modern Forest Retreat with Hot Tub and Sauna - Entire Magda Cabin XL!

Windham, New York, United States

Bed

Bath

Sleeps

$257.74

Gorgeous, newly renovated, corner unit with L shaped deck,2 bedroom, 2 bath with picturesque views featuring main level open floor plan with a kitchen, dining area that seats 8, sitting area, pull-out queen sofa, Air Conditioning, floor to ceiling stone fireplace, large screen tv with WiFi and cable, full bath. Basement has storage area for skis, snowboards and includes new washer/dryer. Sliding glass doors leads to wrap around deck with beautiful views of the natural outdoors with a seating area and a BBQ. Upstairs floor includes second full bath and two spacious bedrooms. Spacious master bedroom includes queen bed and double pull out to sleep total of 4, with TV with cable and 200upstream 10downstream internet service(turbo) and large two door closet. Second bedroom includes bunkbeds and trundle as well as single pull out to sleep a total of 5, with TV /cabe and large two-door closet .Location ideal in the Elm Ridge townhome community with sledding hill on property..5 minute ride to Windham ski Mountain and Town.Check in 2:00 p.m and Check out 11:00am. 15 minute ride to Hunter Mountain with a great spring/ summer Menu of great Entertainment and Zip Line. Golf course 5 min away with music every Friday night in summer. Great Restaurants in town. Enjoy the country in this cozy rustic modern townhouse.All the comforts you can ask for. Ideal for A Family vacation.

Ski, Hike,Bike,Golf, Dine within a 6 min Drive. Perfect for a Family getaway

Windham, New York, United States

Bed

Bath

Sleeps

$514.13

A second Glass Mirrör Haüs cabin, identical in finish to its sister but tucked deeper into the tree line for a more immersive forest setting. The mirrored exterior disappears into the foliage; inside, you have panoramic glass and the kind of stillness only the Catskills deliver.brbrQueen bed with Parachute linens, kitchenette, dining table for two, and a spa-style bathroom with oversized rainfall shower. Radiant heated tile floors keep things warm even on the coldest mornings. Step outside to your private propane fire pit with two Adirondack chairs.brbrBest for couples who want privacy, quiet, and a unique design experience.brbrWHAT'S IN THE CABINbr• 1 Queen bed with Parachute linens, duvets, and pillowsbr• Spa-style ensuite bathroombr• Kitchenette with dining tablebr• Private outdoor propane fire pit with 2 Adirondack chairsbr• Radiant heated tile floorsbr• Samsung Smart TVbr• Amazon Echo Show 5br• Air conditioning and heatingbr• High-speed Wi-Fibr• Forest viewsbrbrON-SITE AT HAUS WINDHAMbr22 private acres · Daily housekeeping · Keyless entry · Fitness center · Infrared sauna · Outdoor sauna · Movie theatre · Billiards room · On-property hiking trails · Free parking · Tesla Destination ChargingbrbrLOCATIONbr3 minutes to Windham Mountain · Walking distance to the Windham Path · Minutes to Windham Country Club · ~2.5 hours from NYC

Cabin

Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway

Windham, New York, United States

1

Bed

1

Bath