House in Windham, NY
8 guests · 3 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Welcome to Windy Hollow! A spacious and newly renovated vacation home with stunning views of Windham Mountain and walking distance 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.
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.
Amenities at NEW - Cozy Modern: Stunning views,3 mins ski,BBQ,Fire Pit,Game Room,walk to town
Non-smoking
No pets allowed
Family friendly
Map of Windham, NY
Ratings and reviews
10.0 / 10.0Outstanding·Jul 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.
10.0 / 10.0Outstanding·Jul 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!
10.0 / 10.0Outstanding·May 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.
10.0 / 10.0Outstanding·Oct 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!
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Top rated by guests
10.0Outstanding
(12 Ratings)
"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..."
Melanie B.Don't miss out! Price and availability may change
