Vacation Rentals By Owner In Windham, NY

Nestled in the heart of Upstate New York, this 2-bedroom, 2-bath apartment offers easy access to Windham’s best summer and winter attractions! Explore the Catskills Mountains while hiking, biking, skiing, or snowboarding just a short drive away from the vacation rental or grab a beer at one of the nearby breweries. When you aren’t shredding the slopes or sightseeing at Five State Lookout, enjoy the spacious yard, fully equipped kitchen, fireplace, and cozy interior of this home-away-from-home.brbr-- THE PROPERTY --brbr1,100 Sq Ft | Fireplace | Free WiFibrbrPerfectly situated for a peaceful Catskills getaway, this well-appointed apartment offers ideal accommodations for a small family or close group of friends.brbrBedroom 1: Queen Bed | Bedroom 2: 2 Queen BedsbrbrKITCHEN: Fully equipped, drip coffee maker, toaster, knife set, dining table, cooking basicsbrINDOOR LIVING: Smart TV, fireplace, dining table, ceiling fansbrGENERAL: Washer & dryer, towels, linens, complimentary toiletries, air conditioning, keyless entrybrFAQ: Pet fee (paid pre-trip)brADDT’L ACCOMMODATIONS: An additional 2-bedroom property for 7 guests is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrPARKING: Driveway (2 vehicles)brbr-- THE LOCATION --brbrOUTDOORS: The Windham Path (0.4 miles), Windham Mountain (2.8 miles), Kaaterskill Falls Trail Head (14.1 miles), Kaaterskill Wild Forest (15.4 miles), North/South Lake (15.6 miles), Dutchman’s Landing Park (24.1 miles), Kaaterskill Clove (24.8 miles), Howe Caverns (41.2 miles)brATTRACTIONS: Five State Lookout (5.7 miles), Mountain Top Arboretum (9.4 miles), Zoom Flume Water Park (10.6 miles), Tannersville (13.0 miles), Village of Catskill (23.4 miles), Hudson (27.4 miles), Home of Franklin D. Roosevelt National Historic Site (58.6 miles)brBREWERIES: Hunter Mountain Brewery (9.8 miles), West Kill Brewing (20.9 miles), Rip Van Winkle Brewing Company (22.4 miles), Subversive Malting + Brewing (23.2 miles), Crossroads Brewing Company (26.6 miles), Keegan Ales (42.4 miles)brAIRPORT: Albany International Airport (61.2 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- Pet friendly with $50 fee (+ fees & taxes)br- No events, parties or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs and may be difficult for guests with limited mobilitybr- NOTE: There are other vacation rental units on-site; other travelers may be present during your stay

Apartment

Spacious Apt w/ Yard: 3 Mi to Windham Mountain

Windham, New York, United States

Bed

Bath

Sleeps

$285.78

Experience year-round adventures at this family-friendly home in the heart of Upstate New York! Boasting 2 bedrooms, 2 baths, and a second-story balcony, this Windham vacation rental is ideal for small families and groups of friends visiting the Catskills Mountains. The private unit is equipped with all the at-home essentials - including free WiFi and work from home space - plus an unbeatable location just minutes from hiking trails, waterfalls, and 4-season fun at Windham Mountain Resort.brbr-- THE PROPERTY --brbrSpacious Deck | Private Entrance | Off-Street Parking | Second-Floor Unit | 1,100 Sq FtbrbrWhether you’re renting out the entire house with your large group or simply seeking a relaxing getaway with your closest loved ones, this apartment makes the ideal resting spot between all your Catskills excursions!brbrBedroom 1: Queen Bed | Bedroom 2: 2 Queen Beds, Twin BedbrbrINDOORS: Open floor plan, 2 flat-screen TVs, dining table, desk area, private second-story balconybrKITCHEN: Fully equipped, cooking essentials, dishware & glassware, drip coffee maker, electric kettle, toaster, dishwasherbrGENERAL: Free WiFi, basic toiletries, linens & towels, air conditioning, keyless entry, stairs requiredbrFAQ: Pet fee (paid pre-trip)brADDT’L ACCOMMODATIONS: An additional 2-bedroom property for 6 guests is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrPARKING: Driveway (2 vehicles)brbr-- THE LOCATION --brbrOUTDOORS: The Windham Path (0.4 miles), Windham Mountain (2.8 miles), Kaaterskill Falls Trail Head (14.1 miles), Kaaterskill Wild Forest (15.4 miles), North/South Lake (15.6 miles), Dutchman’s Landing Park (24.1 miles), Kaaterskill Clove (24.8 miles), Howe Caverns (41.2 miles)brATTRACTIONS: Five State Lookout (5.7 miles), Mountain Top Arboretum (9.4 miles), Zoom Flume Water Park (10.6 miles), Tannersville (13.0 miles), Village of Catskill (23.4 miles), Hudson (27.4 miles), Home of Franklin D. Roosevelt National Historic Site (58.6 miles)brBREWERIES: Hunter Mountain Brewery (9.8 miles), West Kill Brewing (20.9 miles), Rip Van Winkle Brewing Company (22.4 miles), Subversive Malting + Brewing (23.2 miles), Crossroads Brewing Company (26.6 miles), Keegan Ales (42.4 miles)brAIRPORT: Albany International Airport (61.2 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly with $50 fee (+ fees & taxes)br- No events, parties or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: There is another vacation rental unit on-site, and other guests may be present during your staybr- NOTE: The property requires stairs to access and may be difficult for guests with limited mobility

Apartment

Relaxing Catskills Apt < 3 Mi to Windham Mountain!

Windham, New York, United States

Bed

Bath

Sleeps

$802.29

Beautiful four bedroom, four bathroom condo right on the slopes at Windham Mountain in New York's Catskill Mountains. The condo is located in the newest luxury building at Windham, with a heated outdoor swimming pool, two hot tubs, gym, a patio with a fire pit and gas grills available for your use, and a ski locker room that opens right out onto the mountain.brbrThis unit features a master bedroom with a California king sized bed, a second bedroom with a king bed, a third bedroom with two twin over full bunks and a trundle, and an interior bedroom with a twin over twin bunk bed and a trundle. Three of the four bedrooms include a full bathroom en suite, and the fourth bedroom has a bathroom just across the hallway. The fully equipped kitchen includes everything you will need, including a Keurig coffee maker stocked with a selection of coffees. There is also a dishwasher and washer/ dryer in the unit. There is plenty of room for two families.brbrLiving room features a 65 TV with cable and streaming services available. From the living room, walk out to a large balcony overlooking the beautiful scenery of the Catskill Mountains. On the balcony you will find two comfortable Adirondack chairs, as well as a dining set allowing you to enjoy your meals outside.brbrThe building is located at the base of Windham Mountain, and features ski on/ ski off access to the slopes during the winter or mountain biking in the summer. It is a short drive to the town of Windham, and with nearby access to restaurants, mountain biking, golf, horseback riding, zip lining, vineyards and a water park, among other activities.

All Season Luxury Condo in Windham/ Ski On - Ski Off

Windham, New York, United States

Bed

Bath

Sleeps

$261.35

Discover the charming town of Windham, NY, and stay at this spacious 3-bedroom, 1.5-bath vacation rental. With a cozy fireplace, this home offers a warm ambiance for relaxation after days of exploring nearby attractions. Enjoy skiing at Windham Mountain, hiking through the picturesque Catskill Mountains, or driving 10 miles to Hunter Mountain. Then, return home to unwind and plan your next adventure. Whether you seek outdoor thrills or peaceful tranquility, this lovely abode is the ideal escape!brbr-- THE PROPERTY --brbrMountain Views | Furnished Sunroom | Close to Shopping + Dining | Pet Friendly w/ Fee | July 4th Fireworks Viewable Directly From HomebrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Twin Bunk Bed w/ Twin Trundle | Lower-Level Living Space: Queen Sleeper Sofa | Additional Sleeping: Pack 'n PlaybrbrMAIN FEATURES: Private yard, Smart TVs, stereo, fireplace, dining table, books, Bluetooth speakerbrKITCHEN: Dishwasher, stove/oven, refrigerator, microwave, Keurig coffee maker, mixer, toaster oven, dishware + flatware, cooking basics, trash bags + paper towels, high chairbrGENERAL: Free WiFi, washer + dryer, iron/board, laundry detergent, central heating & air conditioning (2nd floor), ceiling fans, complimentary toiletries, linens/towels, hangers, hair dryer, keyless entrybrFAQ: 3 exterior security cameras (outward facing, 1 in garage), pet fee (paid pre-trip)brACCESSIBILITY: Multi-story home, exterior + interior stairs to enterbrPARKING: Driveway (4 vehicles), garage (1 vehicle)brbr-- THE LOCATION --brbrSNOWY FUN: Windham Mountain Club (2 miles), Hunter Mountain Resort (10 miles), Belleayre Mountain Ski Center (31 miles), Catamount Mountain Resort (51 miles) brSCENIC SPOTS: The Windham Path (0.7 miles), Kaaterskill Falls Trailhead (13 miles), Dutchman's Landing Park (25 miles), Kaaterskill Wild Forest (30 miles)brMORE TO DO: Five State Lookout (6 miles), Mountain Top Arboretum (10 miles), Zoom Flume Water Park (11 miles), Howe Caverns (39 miles)brAIRPORT: Albany International Airport (63 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $100 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This multi-story home requires an exterior staircase to enter, and interior stairs are required to access the top and lower levelsbr- NOTE: Your safety matters. The property features 3 exterior security cameras located on the front of the home, the front door facing the driveway, the front entrance as well as inside the garage facing out. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion

Vacation Rental Home ~ 2 Mi to Windham Mountain!

Windham, New York, United States

Bed

Bath

Sleeps

$285.62

Summer Getaway | Close to Activities | Responsive brHosts & Thoughtfully Prepared Home brbrbrEscape to This Windham Retreat for an unforgettable mountain getaway! Perfectly suited for outdoor enthusiasts, this vacation rental townhome offers easy access to golfing nearby and local summer activities. Spend your mornings on the private deck admiring the views before heading out to explore. Your thoughtfully prepared home base awaits—book today!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bed br- Bedroom 2: 2 twin bunk bedsbrbrLIVING FEATURESbr- Furnished deck, balcony, spacious yardbr- Smart TV w/ cablebr- Wood-burning fireplace (wood provided)br- Board games, booksbrbrKITCHENbr- Stove/oven, refrigerator, microwave, dishwasherbr- Drip coffee maker, toaster, kettlebr- Cooking basics, dishware & flatware, spicesbr- Dining tablebrbrGENERALbr- Free WiFibr- Keyless entrybr- Central heatingbr- Linens & towels, washer & dryer, laundry detergent, iron & boardbr- Complimentary toiletries, hair dryerbrbrFAQbr- No A/Cbr- Quiet hours (after 10:00 PM)brbrACCESSIBILITYbr- 2-story homebr- Exterior steps to enterbr- Exterior stairs required to access main and upper levelsbrbrPARKINGbr- Designated parking spots (2 vehicles)brbr-- THE LOCATION --brbrCentrally located near local shops, dining, and year-round outdoor adventurebr2 miles to Windham Path: hiking, cross-country skiing & snowshoeingbr4 miles to Windham Outdoor Rinkbr4 miles to downtown Windham: boutiques, shops, farmers markets & seasonal festivalsbr9 miles to Hunter Mountain Resort: ziplining, skiing & mountain recreationbrUnder 10 miles to Elmridge Forest hiking, Christmans Golf Course, North-South Lake & Tannersville antiquingbr65 miles to Albany International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Please observe quiet hours after 10:00 PMbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires exterior steps to enter. Additional stairs are required to access the main and upper levelsbr- This property does not offer A/C

Windham Retreat w/ Private Deck & Mtn Views!

Windham, New York, United States

Bed

Bath

Sleeps

$1560.27

Escape to a spacious mountain retreat on 5+ private acres, perfect for up to 14 guests. Just 5 minutes from Windham & 16 from Hunter Mountain, this home features a seasonal pool, year-round hot tub, game room with a pool table, and a chef's kitchen. Ideal for family reunions and group getaways seeking adventure and relaxation in the countryside.brbrLIVING & ENTERTAINMENTbr• Two distinct living areas for relaxation and fun.br• Main floor living room with a cozy fireplace.br• Walk-out basement entertainment hub with pool table, karaoke machine, Bluetooth speaker, and a 75-inch HDTV.br• Dedicated office space with a desk and monitor for remote work.brbrKITCHEN & DININGbr• Fully stocked chef’s kitchen with an induction range top and convection oven.br• Coffee options: Nespresso machine and a Keurig Duo Plus (single serve or 12-cup carafe).br• Indoor dining table with seating for 10.br• Kitchen island with additional seating for 4.br• Outdoor dining table with seating for 8.brbrBEDROOMS & BATHSbr• Bedroom 1 (First Floor): King Master Suite with private ensuite bathroom.br• Bedroom 2 (Second Floor): King Master Suite with private ensuite bathroom.br• Bedroom 3 (Second Floor): Queen Bedroom.br• Bedroom 4 (Second Floor): Queen Bedroom.br• Bedroom 5 (Basement): Custom Bunkroom with two Twin-over-Queen beds.br• Bathroom 3 (Second Floor): Full shared bathroom.br• Bathroom 4 (Basement): Full bathroom.br• Bathroom 5 (First Floor): Half bathroom.brbrOUTDOOR LIVINGbr• Heated swimming pool (open seasonally from Memorial Day weekend through the end of September).br• 7-person hot tub (open year-round).br• Weber grill with a searing station.br• Firepit with 8 Adirondack chairs and an ample supply of fire logs.br• Tesla EV Charger and a separate 20-amp outlet.brbrWHY YOU’LL LOVE IT HERE: brWe know what it’s like to stay in a place that forgets the little things. That’s why we’ve stocked our home with everything we wished for in our own travels—comfy beds, quality linens, plush towels, storage space where you need it and so much more. We’ve tried to think of it all so you can simply settle in and enjoy.

Mountain Chalet with Hot Tub & Pool

Windham, New York, United States

Bed

Bath

Sleeps

$233.59

Located in the heart of Windham, Land in the Sky, this newly updated condo is your home away from home. For outdoor adventurers or those looking to have a relaxing getaway, our condo is suited for families of all sizes. We offer year round excitement with a pool, tennis court, fire pit, and picnic areas on-site, as well as Windham Mountain just 3 minutes away (or Hunter Mountain 15 min away) - skiing, snowboarding, tubing, ziplining, hiking, shopping, spas, vineyards, breweries and restaurants.

Cozy Mountain Condo

Windham, New York, United States

Bed

Bath

Sleeps

$1373.09

The poster child for a 'dream house,' this stunning 5-bedroom, 4.5-bath vacation rental is sure to be adored by luxury travelers and architecture lovers alike. Gather your group — friends and family included — to spread out amongst 3,800 meticulously designed square feet, complete with floor-to-ceiling views of Windham Mountain. Venture out for a day on the slopes, or enjoy a staycation at home, where the pool, theater, and outdoor amenities leave little to be desired. The Catskills are calling!brbr-- THE PROPERTY --brbr3,800 Sq Ft | Family Friendly | Mountain & Milky Way Views | 2 Mi to Slopes | On-Site EV ChargerbrbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: King Bed | Bedroom 4: King Bed | Bedroom 5: 2 Queen Bunk BedsbrbrVILLA FEATURES: Smart TV w/ cable, private indoor pool, home theater w/ surround sound system, great room w/ floor-to-ceiling windows & ski resort views, electric fireplace, foosball table & arcade games, dining table, large sectional, en-suite baths, soaking tub, telescope, board games, contemporary furnishings, sleek & modern decorbrOUTDOOR AMENITIES: Wraparound deck w/ dining set & gas grill, patio w/ wood-burning fire pit & Adirondack chairs, en-suite balcony, mountain views, peaceful wooded surroundingsbrCHEF'S KITCHEN: Cooking basics, stainless steel appliances, breakfast bar w/ seating, dishware & flatware, Keurig coffee maker, toaster, blender, ice makerbrGENERAL: Free WiFi, washer/dryer, towels/linens, complimentary toiletries, walk-in closets, hair dryer, iron/board, EV charger (bring your own cable), heated floors, central heating & air conditioningbrACCESSIBILITY: 3-story villa, 3 steps to enter, interior stairsbrFAQ: Optional nightly pool heat fee (paid pre-trip, applied to entire stay), exterior security cameras (4, facing out)brPARKING: Driveway (5 vehicles), EV charger (cable not provided)brbr-- THE LOCATION --brbrWINTER RECREATION: Windham Mountain Club (1 mile), Hunter Mountain Resort (11 miles), Belleayre Mountain Ski Center (30 miles)brSUMMER/FALL ADVENTURE: The Windham Path (3 miles), Elm Ridge Wild Forest (5 miles), C D Lane Park (7 miles), Kaaterskill Falls (17 miles)brFAMILY OUTINGS: Town of Windham (1 mile), Windham Theater (1 mile), Zoom Flume Waterpark (9 miles), Mountain Top Arboretum (12 miles)brAIRPORT: Albany International Airport (48 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This 3-story villa requires 3 steps to enter and interior stairs to access various portions of the housebr- NOTE: There is an optional pool heat fee of $50/night (+ fees & taxes, paid pre-trip, applied to entire stay)br- NOTE: Your safety matters. This property features 4 exterior security cameras. Camera 1 is located on the front of the home facing the driveway, camera 2 is located on the back of the home facing the backyard, camera 3 is located on the back of the home facing the patio, and camera 4 is located on the back left of the home facing the exit of the pool room to the backyard entrance. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motion

Villa

Custom Windham Mtn Villa w/ Pool, Theater & Views!

Windham, New York, United States

Bed

Bath

Sleeps

$1080.0

28 acre semi private lake in the back yard (only 1 other house on the lake). Formerly the White Birches Campsite Lodge. This place is absolutely beautiful. When you walk in, you're met with a gorgeous cabin-style interior. The smell of wood fills the huge, beautiful living/lounge space. Cathedral ceilings with huge barn beams and floor to ceiling fireplace. Multiple glass double doors in the main room leading to the deck allow for a great view of the lake. You would have use of the 325 acres of Department of Environmental Land surrounding the property. brbrThere are many trails for hiking, Cross Country Skiing and Snowshoeing. The previous owner had all 335 acres and sold 10 to me and 325 to Department of Environmental Conservation. Windham mountain is 5 minutes away and Hunter mountain is about 15 minutes away. Large TV and huge fireplace. very large kitchen with granite counters. Groceries are in Hunter or Prattsville both about 15 minutes away. Many great restaurants in the area in Windham, Hunter and Tannersville. We have a grill on the deck with 3 different sections 1 for gas, 1 for coal and 1 for wood. brbrBedroom 1 has a queen bed (sleeps 2).brBedroom 2 has 2 queen beds (sleeps 4).brBedroom 3 has 1 king bed and 1 pull out day bed (sleeps 4)brBedroom 4 has 1 full bed 1 twin bed and twin bunk bed. brOffice has a futon (sleeps 1).brLiving room has 2 couch beds (sleeps 4)brHouse sleeps a total of 15 people comfortably.

Beautiful Lake house on private 28 acre lake

Windham, New York, United States

Bed

Bath

Sleeps

$1303.86

Canadian Log Home on 14 acres yet only 2 miles to Windham Ski Mountain. The house has 4 bedrooms plus a loft and 3 bathrooms. The kitchen is equipped with high end appliances. Living Room with stone fireplace. Sunroom with beautiful mountain views. At the end of a relaxing or busy day enjoy a soak in the hot tub. Wifi. Country Living at IT'S BEST!!! brbrIn the summer Windham is known for hiking, golfing, mountain biking, fly-fishing, hiking, mountain biking, water parks, antiquing, skiing and sleighing. Of course, in the Fall, the foliage is just spectacular. This is not a party group house, this is a home for families.

'Sundance Vistas - Log Home ' - 2 Miles From Windham Ski Mountain

Windham, New York, United States

Bed

Bath

Sleeps

$272.68

Updated Interior w/ Modern Decor & Appliances | Office w/ Dedicated Workspace & Large Windows | Pet Friendly w/ FeebrbrQuick access to the slopes and all the comforts of home await at this Windham vacation rental. Nestled on a deep lot with mountain views inside and out, this 4-bedroom, 2.5-bath home offers a well-equipped space for the whole crew and your furry friend, too! When you aren’t skiing at Windham Mountain Club or hiking Kaaterskill Falls, kick back on the deck and enjoy the view!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 2 twin bedsbr- Bedroom 4: 2 twin bedsbrbrINDOOR LIVINGbr- Smart TVbr- Office, dedicated workspacebr- Dining tablebr- En-Suite bathroombrbrOUTDOOR LIVINGbr- Private yardbr- Deckbr- Wood-burning fire pitbr- Mountain viewbrbrKITCHENbr- Stove/oven, refrigerator, dishwasher, microwavebr- Dishware/flatware, cooking basicsbr- Keurig coffee maker, electric kettle, air fryer, toasterbr- Trash bags & paper towelsbrbrGENERALbr- Free WiFibr- Central heating (oil), 2 window A/C units, ceiling fansbr- Iron/board, hangersbr- Linens/towels, hair dryerbrbrFAQbr- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- Stairs requiredbr- 2-story homebr- Bedroom/full bathroom on 1st floorbrbrPARKINGbr- Gravel driveway (2 vehicles)brbrADDT’L ACCOMMODATIONSbr- There are 4 additional properties available nearby, each with separate nightly rates. If you would like to reserve multiple rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbr- 2 miles to Windham Mountain Clubbr- 0.5 miles to The Windham Pathbr- 9 miles to Hunter Mountain Resortbr- 15 miles to Kaaterskill Falls Trail Headbr- 10 miles to Mountain Top Arboretumbr- 62 miles to Albany International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes, 1 max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires using an exterior staircase to enter but features a bedroom and full bathroom on the 1st floor

2 Mi to Windham Mountain: Scenic Home w/ Fire Pit!

Windham, New York, United States

4

Bed

2

Bath

8

Sleeps

$1772.74

Beautiful, newly renovated three bedroom, three bathroom condo right on the slopes at Windham Mountain in New York's Catskill Mountains. The condo is located in the newest luxury building at Windham, with a heated outdoor swimming pool, two hot tubs, gym, a patio with a fire pit and gas grills available for your use, and a ski locker room that opens right out onto the mountain.brbrThis unit features a master bedroom with a king sized bed, a second bedroom with a queen bed, and a third bedroom with two bunk beds. Each of the bedrooms include a full bathroom en suite. The king and queen bed rooms have mounted smart TVs. The fully equipped kitchen includes everything you will need. There is also a dishwasher and washer/ dryer in the unit. There is plenty of room for two families.brbrLiving room features a 65 TV with streaming services available. From the living room, walk out to a large balcony overlooking the beautiful scenery of the Catskill Mountains. On the balcony you will find two comfortable Adirondack chairs, as well as a dining set allowing you to enjoy your meals outside.brbrThe building is located at the base of Windham Mountain, and features ski on/ ski off access to the slopes during the winter or mountain biking in the summer. It is a short drive to the town of Windham, and with nearby access to restaurants, mountain biking, golf, horseback riding, zip lining, vineyards and a water park, among other activities. There is one parking spot in a heated underground garage with elevator right up to the condo.

Condo on Windham Mountain - Greene County

Windham, New York, United States

Bed

Bath

8

Sleeps

$287.45

Summary:brbrWelcome to your cozy Windham mountain escape, perfectly located just 1 mile from Windham Mountain. This inviting 3-bedroom, 2-bath condo comfortably hosts up to 8 guests, making it ideal for families, friends, and outdoor enthusiasts looking to explore the beauty of the Catskills. Wake up to peaceful mountain views, sip your morning coffee on the private deck, and breathe in the fresh mountain air.brbrbrbrThe Space:brbrThis cozy 3-bedroom condo features a warm, cabin-inspired design with plenty of space for up to 8 guests. The open living area centers around a wood-burning fireplace, perfect for relaxing after a day outdoors. Step onto the private deck to enjoy mountain views or fire up the grill for an easy meal. With thoughtful touches like board games and comfortable furnishings, the space is designed for both relaxation and connection in a true mountain setting.brbrbrbrThe Neighborhood:brbrNestled in the heart of the Windham Mountains, this condo places you steps away from year-round adventure. Hit the slopes at Windham Mountain, explore nearby hiking trails and Kaaterskill Falls, or enjoy local dining and wineries just minutes away. The area offers a peaceful, nature-filled setting with breathtaking views in every season — from snow-covered peaks in winter to lush greenery in summer. It’s the perfect destination for those seeking fresh air, outdoor adventure, and a true Catskills mountain experience.brbrbrbrInteraction with Guests:brbrCheck out our house manual which offers a guide on all information concerning the home and the area. Please message us on your booking platform for any and all questions! We are quick to reply. Host contact information provided for emergencies only

Windham Mountain Condo with Deck & Stunning Views

Windham, New York, United States

Bed

Bath

Sleeps

$479.25

Base of Windham, Large 3 bedroom town home.brbrPlease remember to check WindhamMountain.com Ski Season & Bike Park updates . Please check the mountain site prior to booking for Covid Restrictions. brbrAC in main living space and all bedrooms.brbrPool will be open 7 days starting July 1 to Labor Day. brPool will be closed to Thanksgiving. Pool will then reopen for weekends when WM is open.brbr Community indoor pool with hot tub. Pool closure subject to management. brbrThere is plenty of space. In addition to the 6 beds, there is also a pull out couch and small futon if needed on top of stairs on loft. Space is perfect for a family or 2. brbrThe large unit has private parking for 2 cars. There are extra guest spots but not guaranteed. Bring your groceries and cook, or short drive into town for many local favorites. Basic amenities are included. There is an Apple TV to hook your apple product to living room TV. Master. Bedroom and guest suite have firesticks. There are fans. Main living space has fireplace. Gas Grill on private deck. brbrbrPlease email any questions. brWeekly rate discount available.

Windham Townhouse - Base of Mountain

Windham, New York, United States

Bed

Bath

8

Sleeps

$167.4

Studio for 2 with queen bed. Efficiency kitchen and full bathroom. Access to lake for fishing and swimming in summer and 5 minutes from Windham Mountain for skiers in the winter. 550 gallon hot tub shared with 2 other cabins. Bon fire pit and gas grill. This property was a cross-country ski business so there are hundreds of acres of lettered trails for hiking. We rent canoes and kayaks for the lake. Pet fee $30 per pet per stay

Cabin

Lake Access Studio on Lake Heloise

Windham, New York, United States

Bed

Bath

Sleeps

$481.32

Beautiful Chalet with a host of year-round activities! Close to skiing, snowboarding, sledding, snowshoeing, mountain biking, hiking, golfing, wine tasting, breweries, cideries, Windham and Hunter Mountain Festivals, great restaurants, and more. Relax on the beautiful deck while taking in the mountain views or cozy up to the fire pit. Enjoy a gorgeous modern kitchen, fireplace and wood burning stove. So many amenities including washer, dryer, dishwasher, microwave, stove, coffeemaker, propane BBQ, paper products, and more. Enjoy free High-speed WiFi, Hulu, Disney+, and Prime video or sign in to your own streaming services. Sleeps 11 comfortably. We are pet friendly.

Chalet

Beautiful Windham Chalet 2 minutes to Town and the Mountain

Windham, New York, United States

Bed

Bath

Sleeps

$916.74

Spacious, luxurious, 4500 square foot, 4 bedroom, 3 full bathrooms...hot tub and sauna...20 speaker sound system... home located in the center of downtown Windham...walk to many restaurants and shops...1/2 mile to Ski Mountain... on premise attractions include a triplex movie theatre, Subway & Carvel shops, Game room, 18 hole miniature golf course.....2000 square foot outdoor deck overlooking stream...2 gas fireplaces...radiant heat...large chef's kitchen...open floor dining and living room..ample parking on site

Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham

Windham, New York, United States

Bed

Bath

Sleeps

$3844.8

Copper Ridge Estate | 9BR Luxury Mountain Retreat w/ Theater, Pool, Gym & ConciergebrbrSleeps 18 · 9 Bedrooms · 8+ Baths · Indoor Pool · 2.5 hrs from NYC · Windham, NYbrbr⸻brbrBOOK NOW for the 2025–2026 Ski Season!br2-week stays or full-season (5-month) rentals available.brbr⸻brbrExperience true 5-star mountain living in this 10,000+ sq ft luxury estate perched in the Catskills. Just 2.5 hours from NYC—but a world away from stress—this is your dream winter (or summer) escape.brbrWhether you’re skiing in Windham, hosting a private retreat, or relaxing with family and friends, this home was designed to impress.brbr⸻brbrWhat You’ll Love:brbr9 Spacious Bedrooms (incl. Bunk Room) — Sleeps 18brIndoor Heated PoolbrPrivate 12-Seat TheaterbrFull Gym & Game RoombrExpansive Great Room w/ Wood-Burning Fireplace & Mountain ViewsbrGourmet Kitchen + Breakfast Bar + Multiple Dining AreasbrThoughtful Design Touches & Cozy Lounges Throughoutbrbr⸻brbr Optional Concierge Services (extra fee):br • VIP Ski & Golf Accessbr • Private Instructorsbr • In-Home Spa Servicesbr • Personal Chef, Housekeeping, Serversbr • Restaurant Reservations & Private Eventsbr • Corporate Retreat Planning & MorebrbrLet us customize your luxury mountain getaway.brbrbrPlease note we do have exterior security cameras that are remotely monitored by our alarm company to ensure only registered guests are on the property. Guests are also able to view the same POV from home screen. brWe also have a camera in the pool and the hot tub- for insurance purposes.

EXCLUSIVE, EXQUISITE & UNFORGETTABLE MOUNTAIN OASIS

Windham, New York, United States

Bed

Bath

Sleeps

$1364.79