Windham Hotels with Pools

When you stay at Hotel Vienna 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 hotel is 7.4 mi (12 km) from Windham Vineyards and Winery and 9.2 mi (14.8 km) from Hunter Mountain. Take advantage of recreation opportunities such as an indoor pool or take in the view from a terrace and a garden. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and ski storage. A complimentary continental breakfast is served daily from 7:30 AM to 10:00 AM. Featured amenities include a computer station and express check-out. Free self parking is available onsite. Make yourself at home in one of the 30 air-conditioned rooms featuring refrigerators and DVD players. Rooms have private balconies or patios. 32-inch flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms feature shower/tub combinations, complimentary toiletries, and hair dryers.

There’s a familiar feeling as you cross the bridge over the Batavia Kill and arrive at Wylder Windham. This is where you belong. It’s a place where the sound of laughter mixes with the rustling of leaves, where the flow of the river sets the pace for your day, and the flicker of fireflies illuminates your night.With 20 acres of pastoral land and the Batativa Kill running through it, our family-friendly, all-season resort is filled with endless opportunities for recreation and relaxation. Whether tubing on the river, gathering with friends around the firepit or going skiing at nearby Windham Mountain, this is a place that captures the nostalgic spirit of the Catskills and celebrates the timeless pleasures that this land has to offer.

With a stay at Winwood Condominiums by Windham Mountain Club in Windham, you'll be in the business district, within a 5-minute drive of Windham Mountain Resort and Catskill State Park. This family-friendly hotel is 10.2 mi (16.4 km) from Hunter Mountain and 1 mi (1.6 km) from Windham Country Club. Spend the day on the slopes, or enjoy other recreational amenities, which include a seasonal outdoor pool. Additional features at this hotel include complimentary wireless internet access, concierge services, and an arcade/game room. You'll be on the slopes in no time with the complimentary ski shuttle. Featured amenities include express check-out, a 24-hour front desk, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 48 guestrooms. Complimentary wireless internet access is available to keep you connected. Conveniences include blackout drapes/curtains, and housekeeping is provided daily.

Perfectly cozy destination in the mountains for a weekend getaway or a family vacation. This condo has everything that you will need for you and your family to have a memorable trip! Look no further!!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: 25.About events:No events allowed.

Black Bear Cabin: Your Luxurious Ski, Golf and Mountain RetreatLuxury 3,300 sqft Ski and Golf Chalet with 4 bedrooms + 4 ensuite bathrooms -2 fireplaces.5 min from Windham Mountain Club and 20 min from Hunter Mountain.Cozy & spacious with direct ski mountain views and southern exposure.Large eat-in Chef's kitchen + wine fridge - Large dining area with fireplace.Spacious living room with fireplace - Large rec room + TV/Dolby bar, games, SONOS, pool table, exercise area & Peloton bike.2 Cribs, one high chair and children's tableware and utensils.Propane BBQ and covered outdoor dining area - Firepit for a night of smores & star gazing.Swimming Pool- 34 x 18 salt water, heated swimming pool. Open until November.Available through October, unless extreme weather conditions.Hot Tub- 7 person sophisticated salt water SPA . Available year round.Barrel SaunaNestled in the enchanting landscape of the Catskills, this luxurious 3,300 sqft ski and golf chalet offers unparalleled comfort and elegance:Charming Interiors: Four bedrooms, each with its own en-suite bathroom with all amenities (shampoo, conditioner, bath gel, soap, QTips and body lotion), offering ultimate comfort and privacy.Cozy Atmosphere: Two fireplaces, large living areas, and soaring ceilings that enhance the spacious feel.Family Friendly: Perfect for families, this property has 2 cribs, one high chair and plates and utensils for children.Entertainment Galore: A recreation room equipped with sports and games including a pool table and Peloton bike, as well as 3 smart TVs with a Dolby bar system and HDMI for game consoles.Modern Chef’s Kitchen: Fully equipped with all the essentials and a wine fridge, promoting ease for any wine and cooking enthusiast.Dining Experience: Enjoy meals in a large dining area beside a roaring fireplace or step outside to the propane BBQ and a firepit perfect for stargazing.Additional Amenities:SONOS Music System in multiple rooms for immersive sound.Wine Cellar for storing your select wines.Complimentary wood for the two indoor fireplaces and the outdoor firepitFitness and Relaxation: Exercise area with available equipment, ideal for maintaining wellness during your stay.Stunning Views: Situated with direct views of Windham Mountain and southern exposure for maximum daylight.Entertainment Spaces: Expansive deck with Adirondack chairs, a picnic table for alfresco meals, and a private setting deck.Convenient LocationClose Proximity: Near renowned ski resorts with plentiful shopping, dining, and entertainment options in nearby villages.All-Season Activities: Ski, swim, hike, bike, golf, or explore the trails and outdoor festivities thriving in all seasons.Security: All outdoor spaces are equipped with security cameras for your safety.Pre-Arrival DetailsStart your vacation with ease, as we offer in-home massages, a private chef service, and baby equipment like cribs and high chairs upon request.Late check-out:The check-out time at Black Bear Cabin is 11 a.m, which allows guests to enjoy the morning. However, if possible we do offer the option for you to extend check out to as late as 8 pm. Once booked, you will receive the information on how to request late check-out.Early Check-in:The check-in time at Black Bear Cabin is 4 pm. However, if possible we do offer the option for you to request check-in as early as 10 am, which allows you to enjoy the property for a full day. Once booked, you will receive the information on how to request early check-in.Experience the perfect blend of rustic charm and modern amenities at Black Bear Cabin—a retreat enveloped in natural beauty and ideal for friends and family to gather year-round.Note: All guests must adhere to house rules including no smoking, parties, or unauthorized visitors. Contact us for early check-in or extended stay options. Your host is available to ensure you have a pleasant visit. Please enjoy your stay and leave with cherished memories from this beautiful Catskills destination!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:In order for the booking to not be cancelled, guests must sign the lease agreement sent to them upon booking on VRBO, within 24 hours of receiving it..The primary renter must be at least 30 years old and provide a copy of government issued ID with the signed lease.,If you are below the age of 30, please send us an inquiry describing your group and the purpose of travel for pre-approval..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 30.About events:No events allowed.

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.

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.