NEW - Cozy Modern: Stunning views,3 mins ski,BBQ,Fire Pit,Game Room,walk to town

Windham, New York
$392 avg/night Minimum Stay 2 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 2 nights

Min Stay

Welcome to Windy Hollow! A spacious and newly renovated vacation home with stunning views of Windham Mountain and a block to town. Thoughtfully designed to provide multiple gathering spaces for guests over two levels. We are ideally setup for families and groups. Ski the slopes, hike the trails, bike the mountain, enjoy a round of golf, swim in the lakes, jump in the waterholes, kayak, canoe, take the kids to the waterpark, savor the winery, get spoiled at the spa, relish the Maine Lobster Bake on Saturday nights in the summer or visit our many wonderful local bars/restaurants. However you decide to spend your vacation, Windy Hollow offers a home-away-from-home experience year-around.

Windy Hollow is a spacious home with a warm cozy feel just 0.8 miles from Windham Mountain, 10 miles from Hunter Mountain, and 30 miles from both Belleayre Mountain and Plattekill Mountain. The spaces were designed with our young family in mind and with the intention to make guests feel at ease. We hope your family and friends will enjoy the house as much as we do!

House Layout:

First Floor - One of our favorite spaces in the house is the main living room with high ceilings and a wood-burning stove. You can light a fire or play music and cozy up on the couch while overlooking the beautiful views from our oversized floor to ceiling windows. Taking just a few steps up leads to a spacious private game room for the littles to have their own space. They can play endless board games, read books, or log into any streaming channel on the already Wifi connected TV. Conversely, the space can also be used as a workspace to catch up on email or escape for some quiet time on the couch while fancying a book.

The kitchen and dining area are a few steps up from the living room and feature all new appliances. A well stocked and fully equipped kitchen awaits those inner chefs. Plus a large island with three bar stools provides plenty of room for meal prep, baking, serving food and even enough room to make fresh pasta for the whole family! The dinning room table will accommodate a family of eight for shared meals. One of the fully renovated bathrooms is adjacent to the kitchen for convenience.

Second Floor - All bedrooms are on this level with large closet space. The primary bedroom is a large room with a king size bed, private sitting area and a 65' SMART TV that is Wifi connected and ready for you to log into your streaming channels. Bedroom 2 accommodates up to four guests with a twin and full size bunk bed plus an additional twin bed. This bedroom features three custom windows allowing guests to take in the incredible views of the mountain. Bathroom 2 is fully renovated and located between bedroom 1 and bedroom 2 for easy access. Bedroom 3 is down the hall and features a comfortable queen size bed with large windows to take in the views from upstairs. The new washer and dryer are on this level and ready to use.

During the warmer months enjoy grilling on the large wraparound deck while peepers sing their love songs. Experience the darkest night sky as you fancy a nice cocktail and admire the endless stars. During the cooler months, relish by starring at the ski slopes from the large oversized windows in the living room while cozying up on the couch and sipping on a warm beverage, making Windy Hollow a perfect home during any season.

Close to:

Windham Mountain Club: 0.8 miles (6 EV charging stations)
Union & Post Restaurant 0.8 miles Catskill Mountain Country Store: 0.8 miles
Wylder Hotel Windham 0.9 miles
Babblers Restaurant, Bakery & Bar 0.9 miles
EastWind Lodge & Bar: 0.9 miles Prominence Restaurant: 1.2 miles
Windham Country Club: 1.3 miles
The Windham Path: 1.5 miles
Chicken Run Family Restaurant 1.5 miles Christman’s Windham House: 2 miles
Hayfield: 5.3 miles The Vineyard at Windham: 5.6 miles
CD Lane Park: 5.7 miles
Windham Manor: 5.7 miles Mountain Brook Farm: 7.4 miles
Hunter Ski Mountain: 10 miles
Flume Zoom Waterpark: 10 miles Colgate Lake: 11 miles Tops Friendly Supermarket: 13 miles Hannaford Supermarket: 16 miles Kaaterskill Falls: 18 miles Rail Explorers Catskills: 24miles Belleayre Ski Mountain: 30 miles Plattekill Ski Mountain: 30 miles Hudson Amtrak Train Station: 30 miles Howe Caverns Adventures: 37 miles

Walking distance to:

The Windham Spa
Windham Diner
La Patisserie Normande
Clutch & Throttle Main Street Market
Tap House Grille
Zicatelas
The Windham Local
Millrock Restaurant & Bar Room
Windham Pizzaria
Mountain King Brewing Company. Lilly's Steaks & Cocktails
The Tipp Tavern
Carvel
Subway
Windham Movie Theater Gem Mercantile Country Boutique
Windham Liquor Store Chinese Garden Restaurant

Wildlife in the Catskills - we are situated in the middle of the most beautiful area of the Catskills and nature abounds. You may likely see wildlife during your stay.

All BBQ food items should be brought inside and the grill cleaned after use to avoid having unwanted visitors. Windy Hollow is regularly treated for pests, but being that we are surrounded by nature, it would not be unusual to see a few insects browsing on the deck.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • SKI

    Close To Skiing
  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Recycling Unit Size: 1928 Sq Ft (179 Sq M)
  • KITCHEN

    Coffee/tea Maker Dishwasher Kitchen Island Microwave Oven Paper Towels Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Firepit Gas Grill Outdoor Furniture Patio
  • BATHROOMS

    2 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English Polish Spanish
  • THINGS TO DO

    Basketball Nearby Canoeing Nearby Golf Nearby Kayaking Nearby Mountain Biking Nearby Snow Sports Gear Snowmobiling Nearby Swimming Nearby Water Park Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Arcade/game Room Books Games Smart TV
  • LIVING SPACES

    Fireplace Living Room Wood Stove
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Games
  • LOCATION HIGHLIGHTS

    In The Mountains Near A Health Or Beauty Spa
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevator (single Level Property) Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Rates & Availability

Review Review

  • Melanie B.

    Submitted Jul 22, 2025

    Stayed Jul 17, 2025

    We stayed here in July and it was beautiful. I can only imagine how the view and scenery is during the winter months. We enjoyed our short little stay because it was peaceful, clean and just overall a great place to relax. Would come back again during winter months to just to see. We got to see wildlife all around and a few in the yard in the morning while eating breakfast.

  • Neil C.

    Submitted Jul 13, 2025

    Stayed Jul 11, 2025

    Everything was clean and as described. Check-in was extremely smooth and communication was great. A nice walk into town. Game room was a nice touch. We enjoyed our stay. Thank you!

  • Frank G.

    Submitted May 1, 2025

    Stayed Apr 25, 2025

    Great house with a great location. Very clean and bright with great views of Windham mountain. Beautiful deck to enjoy and morning coffee. Host was on point with all questions answered in a timely manner and great recommendations.

  • Christina G.

    Submitted Oct 27, 2024

    Stayed Oct 25, 2024

    We had a wonderful stay for 3 days at this property! The house was beautiful, clean, comfortable, and well supplied/furnished. We stayed here for my sister’s wedding with our 2 children ages 7 and 10, and my mother in law and her husband. They found the house to be very clean and pretty as well. The kitchen has plenty of nice dishes and cooking equipment, though we didn’t need to cook. The kids loved the nice log bunk beds. The views of the mountains were gorgeous and we were perfectly situated to amenities and Windham Manor where the wedding was held. We would love to stay in this home again! After renting properties for various vacations over the years, it’s rare for us to feel that way. The host was very responsive and flexible!

  • Brian G.

    Submitted Oct 15, 2024

    Stayed Oct 12, 2024

    Our family of four stayed with our friends’ family of four for a long weekend. The house is newly and impressively updated and had plenty of space for the 8 of us. There’s a great game room for the kids, a sunken living room with a view of Windham Mountain, a nicely appointed kitchen with new appliances. Dining area, and full bathroom downstairs, then 3 bedrooms and a full bathroom upstairs. There’s also a wrap around deck and fire pit outside. The house is also very convenient to downtown Windham, within walking distance to several restaurants, shops, and activities. The host was very responsive and accommodating to us. I would recommend this house if you’re looking for a great place to stay in the Catskills/Windham area.

  • Michael S.

    Submitted Oct 6, 2024

    Stayed Sep 28, 2024

    Perfect location to visit the Catskills and walking distance into town was a plus, with many restaurants nearby. New EVERYTHING in kitchen, living spaces, super comfortable inside and on deck. 100% satisfied.

  • Jeff L.

    Submitted Sep 22, 2024

    Stayed Sep 20, 2024

    My family off five came to Windham for a wedding at Windham Manor. We had a delightful stay at this home. Plenty of space, everything was new and in great shape, and the location proved perfect for a short walk into town. The owners were super communicable and easy to work with. Would highly recommend and would stay here again on a future Windham trip.

  • Yvonne M.

    Submitted Sep 3, 2024

    Stayed Aug 23, 2024

    We really enjoyed our stay at Windy Hollow. The property is newly remodelled, nicely designed and furnished, very well equipped - pretty much everything one could want. The property owner was in regular contact to ensure everything ran smoothly with arrival/stay/check-out. We were in the Catskills for a week of cycling and hiking, and both Windham and Windy Hollow were perfect as a base to enjoy all that the region has to offer.

  • Juhaina K.

    Submitted Jul 9, 2024

    Stayed Jul 4, 2024

    We had a wonderful time. The place was brand new and decorated really well. Everything was very clean and equipped well with kitchen utensils, pots, etc. The house was located very close to the Windham town so going anywhere took less than 10 minutes. We will definitely be coming back.

  • Rachel H.

    Submitted Nov 1, 2023

    Stayed Oct 27, 2023

    We loved the renovation and interior design at Windy Hollow, it was spacious, so clean and all updated! The porch/ decks were great for taking in views of the mountains and the den/ game room and locking room relaxation areas were perfect! I don’t think we turned on a tv but being surrounded with beautiful views and the location right at the heart of town it made things so convenient for friends and family to scoop us up for a dinner in town or a trip to the market. The bedrooms were spacious and so comfortable. We would love to return to Windy Hollow!

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Total

Includes taxes and fees
$392+
View details