Windham Hotels with Pools

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.

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. Take advantage of the hotel's room service (during limited hours). 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 minibars. 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.

Located in Windham, Winwood Condominiums by Windham Mountain Club is in the business district, a short 3-minute walk from Catskill State Park and within 2 minutes by car from Windham Country Club. This family-friendly hotel is 10.2 mi (16.4 km) from Hunter Mountain and 15.6 mi (25.2 km) from Kaaterskill Falls. 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.

Located in Windham, this vacation home is in the mountains, within a 10-minute drive of Catskill State Park and Windham Country Club. This vacation home is 11.2 mi (18 km) from Hunter Mountain and 3 mi (4.9 km) from Windham Mountain Resort. Take advantage of recreation opportunities such as a seasonal outdoor pool, or other amenities including complimentary wireless internet access and a picnic area. Free self parking is available onsite. Make yourself comfortable in this vacation home, which has a kitchen. Complimentary wireless internet access is available to keep you connected. Conveniences include a washing machine and an iron/ironing board.

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.

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.

Escape to a private luxury retreat in the Catskills—designed for families and groups seeking space, privacy, and meaningful time together.This 3,300 sq. ft. chalet features 4 ensuite bedrooms, a heated pool (May–Nov), hot tub, sauna, and sweeping mountain views. Just 5 minutes from Windham Mountain, it offers the perfect balance of nature, comfort, and elevated design.Whether you're planning a weekend escape, ski trip, or special gathering, Black Bear Cabin is where lasting memories are made.A Private Retreat Designed for ConnectionWelcome to Black Bear Cabin—a refined mountain escape where architecture, nature, and comfort come together effortlessly.Set against direct views of Windham Mountain, this 3,300 sq. ft. chalet was designed for those who value privacy, space, and a seamless group experience.From the moment you arrive, every detail invites you to slow down, reconnect, and fully enjoy your time together.Space & Privacy Without CompromiseFour bedrooms, each with its own private ensuite bathroomExpansive layout ideal for families, multi-family stays, and retreatsThoughtfully designed to balance togetherness and personal spaceElevated LivingThe main living space features vaulted wood-paneled ceilings, a grand stone fireplace, and a dramatic arched window framing the mountain.It’s a place to gather after a day outdoors—whether for conversation, quiet moments, or simply enjoying the view.Designed for Gathering and HostingFully equipped chef’s kitchen with wine fridgeLarge dining area with fireplaceOutdoor dining patio with BBQ and pizza ovenPerfect for long dinners, shared meals, and effortless entertaining.Entertainment, Seamlessly Built InDedicated recreation room with pool table, poker, and gamesSmart TVs with Dolby sound + SONOS throughoutPeloton and fitness areaEverything is designed so your group never needs to leave to enjoy the experience.Wellness & RelaxationHeated saltwater pool (mid-May through November, weather permitting)7-person hot tubBarrel saunaA private, spa-like setting to unwind in every season.Thoughtfully Family-ReadyCribs, high chair, and children’s essentialsSpacious layout ideal for families traveling togetherSafe, private outdoor environmentThe property is professionally treated to help minimize tick exposure and maintained with preventative measures; however, as with any natural setting, we cannot guarantee a tick-free environment and encourage appropriate precautions during your stay.Outdoor LivingExpansive deck with Adirondack seatingFire pit for evenings under the starsSouthern exposure for natural light throughout the dayUnobstructed mountain viewsPrime Location5 minutes to Windham Mountain Club20 minutes to Hunter MountainClose to hiking, golf, dining, and year-round outdoor activitiesOptional Elevated ServicesEnhance your stay with curated add-ons available upon request:Private chef experiencesIn-home massagePrivate Yoga sessionsSki and winter activity packagesPre-arrival arrangements The ExperienceBlack Bear Cabin is more than a place to stay—it’s a setting designed for connection, celebration, and time well spent.Guest accessGuests enjoy full private access to the entire 3,300 sq. ft. property, including all indoor and outdoor spaces—pool, hot tub, sauna, decks, and recreation areas.Self check-in via secure smart lockNo shared spacesA small number of owner closets and the outdoor shed remain locked for maintenance purposesInteraction with guestsYour stay is designed to feel effortless and private.We offer seamless self check-in and will not be present at the property during your stay. However, we are always available and responsive via the app or phone for anything you may need—from recommendations to assistance—ensuring a smooth and enjoyable experience from start to finish.Other details to noteProperty & SafetyExterior security cameras are installed in outdoor areas (including driveway and pool/hot tub zones) for safety and property monitoringThere are no cameras inside the homeCheck-In & Check-OutCheck-in: 4:00 PMCheck-out: 11:00 AMEarly check-in / late check-out may be available for an additional fee upon request after bookingHouse StandardsTo maintain the quality and experience of the home:No parties or eventsNo smoking or vaping anywhere on the propertyRegistered guests only; no unauthorized visitorsQuiet hours must be respected, especially in the eveningThese standards are strictly enforced to ensure a peaceful environment for all guests and neighbors.Booking RequirementsPrimary renter must be 30+ years oldThe booking guest must be present for the duration of the stayPool, Hot Tub & SaunaUse is at your own risk; children must be supervised at all timesNo glassware permitted in outdoor wellness areasUsage hours apply to ensure safety and respect for neighborsHousekeepingFresh linens and towels are provided at arrivalDaily housekeeping is not includedGuest ServicesOptional services available upon request:Private chefIn-home massageAdditional baby equipmentHoliday BookingsA 7-night minimum applies for Thanksgiving, Christmas, and New Year’s staysDiscounts available for extended staysBooking & House GuidelinesTo ensure a smooth and high-quality experience for all guests, we follow a simple pre-arrival process.After booking, guests will receive a brief summary of house guidelines and be asked to complete a standard rental agreement and provide a valid photo ID for verification.This is a quick and secure step, typical for professionally managed homes, and helps us maintain the quality, safety, and privacy of the experience for everyone.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.

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.

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.