Windham Homestays

When you stay at Albergo Allegria Hotel in Windham, you'll be next to a golf course, within a 5-minute drive of Windham Country Club and Windham Mountain Resort. This golf bed & breakfast is 7.2 mi (11.5 km) from Windham Vineyards and Winery and 9.4 mi (15.2 km) from Hunter Mountain. Take advantage of recreation opportunities such as bicycles to rent or take in the view from a terrace and a garden. This Victorian bed & breakfast also features complimentary wireless internet access, concierge services, and ski storage. Featured amenities include a business center, express check-in, and express check-out. Free self parking is available onsite. Make yourself at home in one of the 21 individually decorated guestrooms, featuring DVD players and flat-screen televisions. Your bed comes with down comforters and premium bedding. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms have complimentary toiletries and hair dryers.

Located in Windham, this cottage is within a 10-minute drive of Catskill State Park and Windham Country Club. This cottage is 12.6 mi (20.3 km) from Hunter Mountain and 3.4 mi (5.5 km) from Windham Mountain Resort. Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and barbecue grills. Free self parking is available onsite. Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Conveniences include a desk and a microwave.

Located in Maplecrest, Mountain Treasure B&B is in the mountains, within a 10-minute drive of Windham Country Club and Elm Ridge Wild Forest. This bed & breakfast is 9.7 mi (15.7 km) from Hunter Mountain and 0.1 mi (0.1 km) from Catskill State Park. Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. This bed & breakfast also features tour/ticket assistance, a picnic area, and barbecue grills. A complimentary full breakfast is served daily. Free self parking is available onsite. Make yourself at home in one of the 6 air-conditioned rooms featuring flat-screen televisions. Your memory foam bed comes with down comforters. Complimentary wireless internet access is available to keep you connected. Bathrooms feature bathtubs or showers, complimentary toiletries, and hair dryers.

HIDDEN GEM IN CATSKILLS.Relax in the fresh mountain air! Light-filled cozy studio on Main St in downtown Windham.Solitude in the Mountains.Beautiful view of ski trails from your balcony!Maximum 3 people. Private entrance.Stay a week and take advantage of our 7 nite 20% Discount!Great Ski Mountain view from balcony!Great walkable downtown Windham . .Private off-street Parking Free Wifi - - Basic Cable -- Linens--Free Coffee/TeaAbout pets:No pets allowed.About children:Children allowed: ages 3-17.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 20.About events:No events allowed.

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.Windy 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!House Layout: First 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. The 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. Second 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. During 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. Close to: Windham Mountain Club: 0.8 miles (6 EV charging stations)Union & Post Restaurant 0.8 miles Catskill Mountain Country Store: 0.8 milesWylder Hotel Windham 0.9 miles Babblers Restaurant, Bakery & Bar 0.9 milesEastWind Lodge & Bar: 0.9 miles Prominence Restaurant: 1.2 milesWindham Country Club: 1.3 miles The Windham Path: 1.5 milesChicken Run Family Restaurant 1.5 miles Christman’s Windham House: 2 milesHayfield: 5.3 miles The Vineyard at Windham: 5.6 milesCD Lane Park: 5.7 milesWindham Manor: 5.7 miles Mountain Brook Farm: 7.4 milesHunter Ski Mountain: 10 milesFlume 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 Walking distance to: The Windham SpaWindham DinerLa Patisserie NormandeClutch & Throttle Main Street MarketTap House GrilleZicatelas The Windham LocalMillrock Restaurant & Bar RoomWindham PizzariaMountain King Brewing Company. Lilly's Steaks & CocktailsThe Tipp TavernCarvel SubwayWindham Movie Theater Gem Mercantile Country Boutique Windham Liquor Store Chinese Garden Restaurant Wildlife 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. All 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.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Basement is not included in rental and remains locked at all times from inside and outside of home. We kindly ask guests to respect our personal space.When using fireplace, please fill/refill stovetop cast iron steamer/humidifier with water throughout stay.,For EV there are 5 charging locations in town including 6 charging station at the Mountain. Windy Hollow is not setup for EV kindly ask not to plug in.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 23.About events:No events allowed.

Step into the heartwarming embrace of history at our enchanting 1800's residence! This cherished abode beckons you with its inviting wrap-around porch, encouraging you to unwind and find serenity. Envision yourself gathered around the fireplace, the very soul of our home, or basking in the crisp mountain air on the deck. Whether you're indulging in the hot tub's soothing waters, sharing laughter by the fire-pit, or shooting hoops on our basketball court – there's a touch of charm for everyone. Ideally situated just 0.2 miles from Main Street and a mere mile from Windham Ski Mountain (with the allure of Hunter Mountain just 10 miles away), our location seamlessly marries convenience with the tranquil melody of a nearby running creek. Families can enjoy local delights in town while feasting their eyes on breathtaking mountain views. As a haven for pets, our home rests peacefully away from the street. The fully finished third-floor cedar loft complete with heating and air conditioning, is a magical space where children weave memories. Our home is a fusion of history, and comfort amenities – where cherished moments blossom into life. Join us in experiencing the perfect blend of charm, warmth, and inviting love. Come stay at our home, and enjoy a retreat getaway with your loved ones – because you all truly deserve it!About pets:Pets allowed: dogs and cats (limit 5 total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Place all garbage inside yellow shed(driveway side of house) Do not leave any garbage outside on deck, as animals will have feast and drag all over..Strip all beds (leave mattress pad on) and leave dirty linens in laundry basket in the room. Place dirty towels in laundry room in laundry baskets.,Lock doors Close windows Shut off lights Run dishwasher BBQ covered, propane off Hot tub cover on Clean up after pets Garbage inside shed.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:Events allowed: family gatherings and birthday parties.Maximum event attendees: 25.

About this spaceSpacious 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.Nestled 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.The spaceWelcome to our Private Townhouse at Crystal Pond Unit! This spacious 3-bedroom, two-bath retreat is the perfect getaway in Windham, New York.As 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.Step 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.Upstairs, 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).Our 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. Whether 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!Other things to noteWelcome 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.Upon 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.We are here to make your stay as enjoyable as possible. Our Property Manager Sue Shaw is at your disposal for any questions or needs.Concierge Services available upon request (private chef, massage, private ski lessons, private yoga classes and more)At 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!About pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Fireplace safety: Place ashes in metal bucket with lid outside (not on back deck) Close the hatch of the fireplace. Don’t overstack..Bookings over 1 week will incur a weekly cleaning fee. Ring video doorbell on property Additional guests over 6 Will incur additional guest fee,Gather used towels Throw trash away Turn Thermostat down to 55F Turn off lights Enjoy your stay and treat our home with care as if it were yours..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

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.About pets:No pets allowed.About children:Children allowed: ages 0-17.About customRules:Quiet hours start a 10pm..About smoking:Smoking is not permitted.About events:No events allowed.

Welcome to the newly renovated house with central Heating and Cooling located just minutes from skiing, hiking and everything the Catskills can offer. Experience relaxing and rejuvenating time in the 3 bedroom, 2 bathroom home which can comfortably accommodate 6 to 8 guests. The house is furnished with a king size bed in the master bedroom, full size bed in bedroom 2 and a twin over full bunk bed in bedroom 3. Bunk-bed also comes with a twin size trundle totaling 3 separate beds. While there are amazing dining options within 5-10 minute driving distance our kitchen is fully stocked with all the essentials you will need to prepare yourself all the meals. The craft ice from the fridge will help you entertain and relax with a fancy chilled drink of your choice.Conveniently located 6 min from Windham Mountain, 15 min from Hunter Mountain and 40 min from Belleayre Mountain, the location provides the visitors with options for skiing, snowboarding and hiking. The outdoors activities are endless. You can choose between horseback riding, fishing, golfing, mountain biking, ziplining, birdwatching. You can visit one of the tallest waterfalls in New York - Kaaterskill Falls located just 20 min away. If you choose to relax without the hassle of driving and moving around however, the 1-acre property backs to the state land. You can enjoy reading a book or vibe in the hammock with a calming and soothing sounds of the creek running your round through the back of the property.A Level 2 EV charger is available on-site at no extra cost.No pets, please - we aim to keep the space allergy friendly for all guests.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Discover this marvelous 3-bedroom gem in Windham. This delightful condo features 2 king beds and 2 sets of bunk beds, perfect for a family getaway. With 3 bathrooms, including jetted bathtubs, guests can relax and unwind after a day of exploring, skiing, hiking and adventuring! All the amenities are here - washer/dryer, WiFi, Fitness Center, POOL. Windham is the Gem of the Catskills and the Enclave is the Gem of Windham! Enjoy four-season adventure and excitement at the Enclave. Ski right from your doorstep in the winter, and hike right up the mountain in the summer. Enjoy fly-fishing, hiking, mountain climbing, mountain biking in the summer. Ski-in/ski-out all winter long. After skiing, enjoy the pool or hot tub. We hope you enjoy what our place and Windham has to offer.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 24.About events:No events allowed.