Vacation Home Rentals By Owner In Windham, NY

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

$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

$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

$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

$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

Bed

Bath

8

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

1

Bath

6

Sleeps

$351.0

Welcome to our cozy getaway! Enjoy easy access to some of the best skiing in New York, just a 5 minute car ride to Windham Mountain or take the 1 mile walk to downtown. Our townhome has 3 bedrooms, 2 full bathrooms, and a sleeping loft. On the main level, you will find a warm & inviting fireplace in the living room. There is a patio off the back of the house with sensational views of the mountain. There is a mudroom upon entry which is great for unloading. The second floor has 2 bedrooms (one queen bed and a double/full bed). There is a full bathroom on the second floor, as well as, a loft/den area with a futon that pulls out into a double/full bed for additional sleeping.

Cozy Windham Getaway

Windham, New York, United States

Bed

Bath

Sleeps

$427.63

Welcome to a “Change of Altitude,” an immaculate 3 Bedroom/3 Bath Townhouse that’s a short walk from Windham Main Lodge and ski lifts. Enjoy the development’s indoor heated pool with hot tub, gym and lounge that’s just a few steps away from this home. Plus, check out the Alpine Spa (open in winter) and many great local restaurants when taking a break from the slopes. brbrWindham has tons to offer visitors all season long with beautiful hiking trails, local wineries, shopping, festivals, and sight-seeing throughout the Catskills. Plus, enjoy the tennis courts in the housing development. brbrThis renovated property comfortably sleeps 10. One bedroom features a King bed with a Twin trundle. Another bedroom has two sets of XL Twin bunkbeds with a XL Twin trundle. Finally, a third bedroom has a Queen bed with a bunkbed that features a Full-sized bed (lower) and Twin bed (upper)brbrHeated floors will give you a cozy stay. Fully equipped kitchen. Mudroom. Washer and Dryer. No Smoking. No Pets.brbr*Travel insurance is highly recommended as last minute cancellations are not offered due to illness and inclement weather.

Amazing Location, Steps Away from Magic Carpet to Main Lodge.

Windham, New York, United States

3

Bed

3

Bath

10

Sleeps

$591.0

Hyttå is a private, Scandinavian-inspired mountain retreat set on 6 wooded acres, offering complete privacy just 6 minutes from downtown Windham. The home is a beautifully restored 1840s timber-framed barn, thoughtfully updated with modern Nordic design while preserving its historic character. The property already has several 5-star ratings on other travel sites, and now we`re just launching it on VRBO as well!brbrThe main house includes 4 bedrooms, 2 bathrooms, and a fully equipped kitchen, making it well suited for ski weekends, holidays, and relaxed group getaways. The layout is comfortable and practical, allowing guests to spend time together while still having space to unwind.brbrA unique highlight of the property is the private clubhouse, known as The Northern Lights Bar, located just steps from the main house and exclusively for guest use. Inspired by Norwegian après-ski culture, the space features a full-size bar, shuffleboard, karaoke, comfortable lounge seating, and a projector with motorized screen for movie nights. A custom Northern Lights–inspired light installation adds a distinctive atmosphere. Because the clubhouse is separate from the main house, guests can enjoy it without disturbing others.brbrOutside, guests can relax in the brand-new Caldera 6-person hot tub, with views of the trees and vast backyard. The property is accessed by a long, winding driveway (no 4WD required) and offers ample parking.brbrHyttå is ideally located for exploring the Catskills. Windham Mountain is 9 minutes away, Hunter Mountain is 20 minutes, and nearby towns including Catskill, Hudson, Woodstock, and Kingston are all within an hour’s drive, making it easy to balance outdoor activities with shopping, dining, and sightseeing.brbrThe home is comfortable for guests of all ages, and we can provide a travel crib, high chair, and unobtrusive baby gates upon request. Well-behaved dogs are welcome with prior approval (fees apply).brbrHyttå is a place we genuinely love and use ourselves. We ask that guests, two-legged and four-legged alike, treat the home with the same respect. We take pride in hosting with care and aim to provide a comfortable, well-maintained home where guests can relax, reconnect, and enjoy the mountains year-round.

Hyttå, Cozy Nordic Retreat, Hot Tub, Clubhouse, Wifi

Windham, New York, United States

Bed

Bath

Sleeps

$598.84

Summary:brbrWelcome to 24 Timber Trail, a luxurious and cozy mountain retreat designed for unforgettable gatherings in the heart of the Catskills. Perfect for families, groups, and ski goers, this spacious 4-bedroom, 5-bath home comfortably accommodates up to 12 guests and offers panoramic mountain views from every angle.brbrbrbrStep into a warm, inviting space where modern comfort meets rustic charm. The open-concept layout features soaring ceilings, large windows that frame the breathtaking scenery, and plenty of seating for everyone to relax and connect. Whether you’re cooking in the fully equipped kitchen, dining together, or lounging by the fireplace, every corner of this home is made for comfort and connection.brbrbrbrStep outside onto the expansive deck to soak in sweeping views of the wilderness, enjoy a meal al fresco, or unwind by the outdoor fire pit under a starlit sky. The home’s spacious design makes it perfect for entertaining large groups, hosting family reunions, or simply escaping the city for a peaceful mountain getaway.brbrbrbrLocated just 10 minutes from Windham Mountain and close to Hunter Mountain, you’ll have easy access to year-round adventure—from skiing and snowboarding to hiking, golfing, and fishing. After a day of exploring, return to your serene retreat and take in the beauty of the Catskills from your private deck.brbrWhether you’re here for the panoramic views, the cozy ambiance, or the nearby outdoor attractions, 24 Timber Trail offers the perfect balance of luxury, comfort, and nature.brbrbrbrGather your group and escape to 24 Timber Trail, a luxurious mountain home with breathtaking panoramic views. Just 10 minutes from Windham Mountain, this spacious retreat features 4 bedrooms, 5 baths, and a large deck perfect for soaking in the scenery. Enjoy cozy nights by the fire pit, cook together in the open kitchen, or simply relax in comfort surrounded by wilderness. Ideal for families, groups, and ski goers, it’s the ultimate Catskills getaway for those seeking space, style, and serenity.brbrbrbrThe Space:brbrMain Floorbrbr-King Master with fireplace and full bathroom with double sink, sliding door to deckbrbr-Kitchenbrbr-Living room with wood burning stovebrbr-Half bathroombrbr-Dining roombrbrbrbrSecond Floorbrbr-Loft with pull out queen chaise couchbrbr-Bedroom, full bathroom with whirlpool and shower, full bed with trundle brbr-Bedroom with full bathroom, queen bedbrbrbrbrLower level (Basement)brbr-Bedroom with king bedbrbr-full common bathroombrbr-living room with chaise couch pull out queen bed. brbr-laundry room brbrbrbr2 Floor AC unitsbrbrbrbrOther 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: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..

Spacious Mountain Home | Fire Pit & Panoramic Views

Windham, New York, United States

Bed

5

Bath

12

Sleeps

$1395.0

Get ready to relax in this slope-side 4-bedroom townhome in Windham, perfectly situated at the base of the mountain. In the summer months, enjoy easy walks to the communal pool and hot tubs—ideal for unwinding after a day outdoors. Whether you’re hiking, biking, or just soaking in the fresh mountain air, this is the perfect home base for families or groups.brbrInside, the home features a king bed, queen bed, full bed, bunk bed, and twin bed to comfortably accommodate everyone. With 4.5 bathrooms, there’s plenty of space and privacy for a seamless stay.brbrThe townhome is comfortable year-round with both heating and AC, making it a great escape in any season. Whether you’re relaxing after a day of adventure or gathering for a laid-back evening in, this home has everything you need.brbrCome experience Windham in the summer—right from your doorstep.

Ski in / Ski out - Spacious 4-bedroom townhome in Windham

Windham, New York, United States

Bed

Bath

11

Sleeps

$1431.0

Enjoy a relaxing stay at this gorgeous rustic lodge on 10 acres abutting a 28 acre lake surrounded bybover 300 avrea of protected watershed lands called Hayden Preserve. Enjoy the scenic beauty of Mt Hatden surrounding lake Heloise and the abundant wildlife. brNowbif fishing is your game the lake is full of bass, perch, and sunnys just to name a few. brThe lodge comes equipped with most amenities including an outdoor gass grill for use. brThere are additional fees for canoe and kayak rentals, rotisserie BBQ grill, and extra firewood. brThe surrounding Windham resort area has some great year round fun with something to fit everyone's tastes.brWe are available for weddings and other events for an additional charge. Hope see you soon.

Serendipity Lake House on Lake Heloise. Beautiful private 4000 sq ft lodge

Windham, New York, United States

Bed

Bath

Sleeps

$435.27

Windham Mountain Retreat | Private 5-Acre Catskills Getaway w/ Treehouse, Game Room & ViewsbrbrWelcome to your Catskills vacation rental in the heart of Windham, NY — a spacious four-season mountain home set on 5 private acres with scenic views, private hiking trails, a pond, playground, and a magical treehouse. Just minutes from Windham Mountain Ski Resort, this secluded retreat offers the perfect balance of privacy, comfort, and convenience.brbrIdeal for families, large groups, reunions, ski trips, retreats, and romantic getaways, this home is close to all the action yet tucked away for complete peace and tranquility.brbrPrime Location – Minutes from Top Catskills Attractionsbrbr3 miles to Windham Mountain (family-friendly skiing & snowboarding)brbr9 miles to Hunter Mountainbrbr2 miles to Windham Country Club (18-hole championship golf)brbrNear Kaaterskill Falls, hiking trails, biking, snowmobiling & horseback ridingbrbrClose to Windham village dining, bars, festivals & art galleriesbrbrPerfect for Every SeasonbrbrWhether you’re planning a winter ski getaway, summer family vacation, fall foliage escape, or spring retreat, Windham offers year-round outdoor adventure including skiing, hiking, golfing, biking, and more.brbrComfortable Mountain LivingbrbrAfter a day exploring the Catskills, relax in this warm and inviting chalet-style home. Enjoy:brbrCozy fireplace for relaxing eveningsbrbrGame room with ping pong, foosball, dartboard & board gamesbrbrKid-friendly amenities including Legos & Barbie playsetsbrbrScenic back porch with grill for outdoor diningbrbrPeaceful nature views in every directionbrbrOutdoor Space Guests LovebrbrPrivate hiking trails on the propertybrbrSerene pond & wooded acreagebrbrChildren’s playgroundbrbrUnique treehouse experiencebrbrIdeal setting for gatherings, holidays & memory-makingbrbrWhether you’re unwinding by the fire, hosting a family reunion, enjoying après-ski evenings, or reconnecting with nature, this Windham Mountain vacation home is the perfect Catskills escape.brbrBook now and experience one of the most unique and private vacation rentals in Windham.

Windham Mountain Chalet with Treehouse sleeps 15, Game Room & fireplace

Windham, New York, United States

Bed

Bath

Sleeps

$392.07

Welcome to Windy Hollow! A spacious and newly renovated vacation home with stunning views of Windham Mountain and a block 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

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$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

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