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.

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.

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.

Beautiful newly built 1200 sq ft cozy log guest house, w vaulted ceiling’s and a gas fireplace for a charming indoor experience. Air conditioning for those few warm summer days. A mud room with bench seating and ski storage area. w a heated floor. An outdoor Adirondack chair seating area w a gas fire table for a peaceful outdoor evening surrounded by a serene tree lined environment.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.

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.

Unit 2: This brand new 3600 square foot townhome boasts 5 bedroom and 5 1/2 baths directly across from Windham Mountain. Since every bedroom has its own bathroom (4 of which are en-suite) everyone will have their own space! During the winter you can walk to skiing and the adventure park. But if warmer weather is for you then ride your mountain bike right out of your front door or drive a mile to the golf course. You can enjoy 365 day views of the ski area from 1000 square feet of outdoor decks. Although the spacious kitchen/dining/living area can accommodate large families or groups if you want to give everyone a break from cooking and cleaning you can enjoy all that Main Street has to offer less then a half mile away. Personal door code will be provided upon booking.About pets:Pets allowed: limit 2 total.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: 21.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 50.

Unit 3: This brand new 3600 square foot townhome boasts 5 bedroom and 5 1/2 baths directly across from Windham Mountain. Since every bedroom has its own bathroom (4 of which are en-suite) everyone will have their own space! During the winter you can walk to skiing and the adventure park. But if warmer weather is for you then ride your mountain bike right out of your front door or drive a mile to the golf course. You can enjoy 365 day views of the ski area from 1000 square feet of outdoor decks. Although the spacious kitchen/dining/living area can accommodate large families or groups if you want to give everyone a break from cooking and cleaning you can enjoy all that Main Street has to offer less then a half mile away. Personal door code will be provided upon booking.About pets:Pets allowed: limit 2 total.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:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 50.

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.

Escape to Windham in this beautifully designed, pet-friendly home—just a 2-minute walk to the village’s charming shops, farmers market, scenic creek, and fun family spots like the movie theater, mini golf, and arcade. Only a 2-minute drive to Windham Ski Resort. With a private hot tub, indoor fireplace, and a perfect mix of vintage character and modern style, this cozy mountain retreat is ideal for families, friends, and creatives seeking a memorable getaway!The space- 2-Minute walk to town- Outdoor Fire Pit- 7 Person Hot Tub- 2 Car Private Parking (Street Parking Available)- Fully Equipped Kitchen- Outdoor Seating- Sun Room- Smart TVs, Hi-Speed WiFi- Board Games- Large Garage Space for Games- Cornhole Set, Ping Pong Table, Arcade Basketball- Pet Friendly- Indoor Fire Place- 2-Minute Drive to Windham Mountain Club- 16-Minute Drive to Hunter Mountain- Right next to Carvel, Mini Golf, Arcade, Windham Movie TheatreFIRST LEVEL- Living Room:When you walk in, you’ll be greeted by a serene, cozy gathering space with plenty of comfy seating. Sink into the plush couch or spin around in our fun swivel chair (bonus: it hides extra throws!). It's the perfect spot to curl up with a book or kick back and watch a movie by the warmth of the indoor fireplace.- Kitchen & Dining:Fully equipped kitchen with every item of cookware, silverware, and much more. Coffee machine, toaster, blender and tea kettle are all available for your stay.There is a washer and dryer located in the kitchen.- Bedroom #11 king bed, a dresser, and a closet with hangers and extra linens.- Bedroom #42 bunk beds. It has 2 large pullout drawers for storage.SECOND LEVEL- Bedroom #21 king bed, a dresser with a TV, and closet with hangers and extra linens.- Bedroom #32 full beds, a pullout couch (full size)- Full bathroomEach floor has one full bathroom. Both are walk-in-showers (no tubs).- Outdoor SpaceUnwind in the hot tub under cozy string lights. There is an umbrella to shield you from the sun or rain. The fire pit area has four Adirondack chairs with extendable leg rests, adjustable angles, and handy trays for your drinks or phone. The fire pit doubles as a grill—or pop the lid on and it becomes a table!Guest accessGuests have access to the entire home. Please be respectful of the neighbors at all times.Other things to noteWe have below available upon request:- Pack & Play (Travel Crib)- Bassinet- Highchair- WagonDog Policy:Dogs are not allowed on furniture or beds.Extra fees will incur if hair is found on furniture or bedding.DO NOT leave dogs unattended under any circumstances.Please be considerate of the neighbors at all times.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: 18.About events:No events allowed.

With a stay at this cottage in Windham, you'll be within a 10-minute drive of Windham Mountain Resort and Catskill State Park. This cottage is 12.6 mi (20.3 km) from Hunter Mountain and 3.5 mi (5.6 km) from Windham Country Club. 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.