Find Chalets in Windham

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.

With a stay at this chalet in Windham, you'll be in the mountains, within a 10-minute drive of Windham Mountain Resort and Catskill State Park. This chalet is 10.7 mi (17.3 km) from Hunter Mountain and 1.9 mi (3.1 km) from Windham Country Club. Take advantage of recreation opportunities including a hot tub and a sauna. Free self parking is available onsite. There's a private furnished balcony/patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. A 50-inch Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected. The bathroom features complimentary toiletries and a hair dryer. Conveniences include a microwave and a coffee/tea maker, and you can also request a crib/infant bed (complimentary).