Boutique Hotels in Windham

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.

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.

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.

The highest Mountain View’s with Ski Windham as well as Hunter Mountain ski slope views and Valley Views . A breathtaking environment with 3 outdoor fire-pits and lake views as well as town views. 5 ⭐️ The property is 5 acres of tranquility, with walking paths through beautiful gardens with a ski chair lift in front of one firepit and 4 Adirondack chairs in front of another. The best is a Japanese style garden with serenity and lake views with the entire landscape of mountains in your view. Every room in the home has the Mountain View’s as well as both ski slope views. You can enjoy walking out under a covered porch to the hot tub that also shares the same views , or to the outdoor bbq grill while taking in the beautiful mountain range and town of Windham. The interior of the home has a comfortable environment with two warm gas fireplaces. One in Living room as well as one in the dining room/ kitchen area with tvs above each one. The lower level living room has a large 72” tv with two comfortable couches and a full oak bar in the adjoining room with a pool table as well as foosball and ms Pac-Man game.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: 25.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.

This Windham cabin minutes from Hunter and Windham Mountains, boasts 6 inviting bedrooms, including 1 king bed, 4 queen beds, and 3 bunk beds. With amenities like WiFi, heating, and a washing machine, guests can relax and unwind in this beautiful retreat. The 7 bathrooms ensure everyone has their own space to freshen up. Guests can enjoy scenic views, total privacy, sprawling landscape and truly beautiful hiking trails all on the property. Everything you need for a short or extended stay is here on the property. With local vineyards and 2 ski mountains within 20 minutes, it is truly a year round getaway for anyone looking to relax and decompress. The town is about 5 minutes drive and boasts upscale as well as family dining options, local markets and merchants, and just about anything you might need during your stay. Fall in love with Windham and enjoy the magic it 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:Flexible check-in available (contact host in advance of arrival).About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 26.About events:No events allowed.

Relax in this beautiful natural setting course that Windham has to offer, while at the same time enjoying all comforts of home with stunning views of the mountains and Surrounded by the Golf courseYes! The house is located in the unique location in the middle of the Golf course and with the ski slopes view. Just minutes from downtown Windham, you’ll be in proximity to all the best of the Catskills: Golf, ski, biking, water park, waterfalls, hiking trails lakes, dining, and wineryAbout pets:Pets allowed: dogs less than 20 lbs per pet (limit one pet total).100$ charge for pets Only small pets !.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:For the safety and comfort of all guests, firearms and other weapons are strictly prohibited on the property. - no fireworks.-The maximum occupancy for this property is 8 people, including children and infants. Please ensure your group size does not exceed this limit.,- For safety reasons, the use of candles is not permitted inside the house. -Hunting is not permitted on or around the property..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 27.About events:No events allowed.

Our charming timber frame home offers a unique aesthetic appeal - a harmonious combination of rustic warmth and modern function. This mountain retreat offers flowing open spaces throughout. Vaulted pine tongue & groove ceilings, exposed wood beams, and a blue stone fireplace that compliments the home's rustic elements and wood floors. Skylights allow for bright-inviting spaces. The home is set on a private 2.5 acre lot surrounded by trees, while offering the convenience of town only several minutes down the road.Our home has 4 bedrooms and 3 full bathrooms. The upper level of the home has an open concept layout with an updated kitchen, dining area with seating for 8 (plus 3 counter stools), living room with fireplace, and master bedroom with full bath (shower/tub). There is a mudroom as you enter for shoes, equipment, etc. The deck is located off the main living area and includes a grill and an outdoor dining table with views of the mountain. Firewood is available for use in the wood shed on the side of the house.The lower level features a family room with wood pellet stove, a 2nd master bedroom with full bath (shower/tub), and 2 additional bedrooms that share a 3rd full bathroom (shower with bench). There is also a beautiful sunroom off the 2nd master, with high ceilings and tons of light, that leads out to the large private backyard (and fire pit!). The laundry room is on the lower level as well. We have board games, puzzles, and a small air hockey table for those days you want to stay in and relax. This is a great home for 2 families and we also welcome dogs!Please note we have our well water tested annually through Adirondack Environmental Services located in Albany to ensure the drinking water is potable.Your destination awaits and is just minutes away from:- 3 to 4 mins away from Town and restaurants- 5 mins away from the Windham Mountain Resort- 15 to 20 mins away from the Hunter Mountain Resort- 20 mins to Colgate Lake State park- 25 to 30 mins away from Kaaterskill Falls & TrailsMust be at least 26 years of age to rent this property.Additional $200 cleaning fee (per stay).Pets are welcome - additional $50 fee (per stay).** Please note - we ask that Guests: - Clean the fireplace (if used) prior to checkout- Clean all dirty dishes prior to checkout- Remove all garbage & recycling (there is no garbage pick up so all garbage needs to be brought to the Windham Transfer station 3 minutes from the house)- Leave the house in good conditionIn addition:1. The home must be left in the condition you found it. Please do not move any of the furniture. We understand that accidents happen so please let us know if something is broken. It is only fair that we have ample time to replace something before the next guests arrive.2. NO Smoking inside the house. If Smoking outside, please dispose of cigarette butts appropriately (do not throw anywhere on the property or in the house garbage pail).3. No fires inside or out are to be left unattended. Please make sure that all embers in the fireplace are completely out before closing the flue and retiring for the evening.4. Our cleaners are there to do the laundry, dust and clean the kitchen and baths (not clean up large messes left by disrespectful guests!)5. Do not flush anything other than toilet paper. Do not flush wipes of any kind. No feminine products should be flushed at anytime.6. The house is located in the woods. Although we perform regular pest control on the house, we cannot guarantee it to be pest free of all bugs and pests. We cannot compensate for the presence of pests, insects and animals. Although food is biodegradable it is not safe or recommended to dispose any food items or trash in the woods for it attracts insects and animals.7. Please be aware that we have 3 outdoor cameras installed for security purposes. Once you arrive at the house, all cameras are disarmed for the remainder of your stay. No cameras are located inside the house.For your convenience, the home is maintained by compassionate hosts with a dedicated caretaker, happy to address any questions or concerns that you and your guests may have.About pets:Pets allowed: dogs (limit 1 total).Additional $50 fee required..About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Garbage and Recycling Removal - must bring to Windham Transfer Station. Cost is $3 per trash bag (cash only); recycling free. If not, $50 charge..Fireplace - if used, guests must clean fireplace prior to check-out. If not cleaned, guest will be charged $50 (withheld from security deposit).,Dirty dishes - must be cleaned (or run through the dishwasher). If not cleaned, guest will be charged $50 (withheld from security deposit)..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 28.About events:No events allowed.

True mountain getaway, just 2.5 hours from NYC!! Modern and clean 2 bedroom 2 bathroom townhouse minutes to Windham Mountain. Enjoy beautiful wood-burning fireplace, Roku TV and high speed Wi-Fi perfect for remote work. Amenities include outdoor pool (open from Memorial through Labor Day), pickleball, basketball and tennis courts, as well as a fire pit with Adirondack chairs. Very close to town and the amazing escarpment hiking and Elm Ridge mountain bike trails. NOW OPEN FOR 2024/25 SKI SEASON!!The spaceThis is a spacious two bedroom, two bathroom condo, with a fully-stocked kitchen and a living room with fireplace. Full kitchen, oven & stove-top, fridge, microwave, coffee maker and dishwasher. There is a large private back deck to enjoy the outdoors.The spacious master bedroom has a comfortable queen size bed. The second bedroom has twin over full bunk beds and a separate twin bed. There are two full baths, one on each floor.Relax in our living room on the new comfy couch which faces the wood-burning fireplace. The living room also features a flat screen TV with Roku and Wi-Fi. A roaring fire will keep you warm even on the coldest nights. The condo has A/C for the summer months. There is also a tower fan in each bedroom.The condo comes fully stocked with all the essentials you need to have your ultimate mountain escape! Towels, linens and toiletries are provided. Ideal for 6 people to enjoy.Guest accessYou will have access to the whole condo including all of the complex amenities: laundry in complex (different building), outdoor pool and two tennis courts.Interaction with guestsWe will be available via phone/text in case you run into any problems during your stay. There is a property manager on site in the event there s a problem.Other things to noteEarly bird check-in (9 am) and Twilight check-out (5 pm) are available for a fee. Subject to availability.Bring your firewood with you or pick it up in Hickory Hill Market down the road or gas station nearby.There are security cameras located above the front door overlooking the parking lot to ensure safety of our guests. It does not look into any interior spaces.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Please take shoes off in house.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.

Beautiful Country Setting 3 min to Windham town center w Large deck/ New Hot Tub and Large Wood Fire pit across our bridge next to a wonderful Stream w 6 cedar Adirondack chairs surrounding our fire pit. A serene setting of 6 chairs on a new bluestone patio stream side, for morning coffee or evening drinks listening and watching the running water closeup.Enjoy one of our newest amenities , a fun game of bocce just next to our fire pit,bean bag toss. Ultra Modern spacious kitchen with a Barista Breville Espresso Cappuccino machine with built in grinder, comfortable living room with flat screen TV , DVD , WiFi , DIRECTV, HBO ,charming pellet stove,1906 antique player piano. 2 person shower for relaxation after a hike or skiing. Large deck, with barbecue and outdoor flat screen tv 50” on deck, with a gas fire pit in front of couch on deck, with stream behind house. . A assortment of board games , horse shoes. Wake up to deer in the backyard or walk across the street to see the beautiful horses or sheep. A short drive to a beautiful walking , or cross country skiing path with beautiful views. Great location for Hiking or a relaxing day on the golf course. Zip lining 15 minutes away, or relax and take in a movie at the local 3 screen theatre right in town. Zoom Flume water park a 8 min drive. A short drive to Main st in town 2.1 miles and 3.4 miles to Ski Windham, and Hunter Mtn Ski area 15 min drive .A 12 min drive to CD lane park that has beachfront on a lake. Also a 25 min drive to North Lake and South Lake that are beautiful large lakes for lying on the beach, or renting a kayak or bring your own. Also some breathtaking views at the beautiful 5 state view at the Historic site of the Catskill Mountain House and Boulder Rock, and visit the Kaaterskill water fall overlook or take a beautiful hike up from the bottom of the falls to inspiration point . Also we have a wide selection of excellent restaurants in town and in the area. A short 40 min drive will bring you to the beautiful Historic town of Hudson. The town has many fine restaurants and tremendous character along with many interesting antique shops and more. The property has outdoor security cameras facing the front driveway and bridge and streamside patio for security and insurance purposes.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:(Firewood/ starters available at Hickory Hill gas station and Smittys nursery Rt23 in town).About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.You may smoke outside on deck area!.About minBookingAge:Minimum age to rent: 20.About events:No events allowed.