See all properties
Chalet

Chalet nestled right in Windham Mountain's quiet beauty-private access to trails

Photo gallery for Chalet nestled right in Windham Mountain's quiet beauty-private access to trails

Wonderful Windham Winter Wonderland!
Relax and enjoy stunning Mountain View’s from large and secluded deck
1st Floor Master Bedroom with en suite bathroom, wide smart tv, walk-in closet
King guest room with en-suite bathroom. (Sleeps 2)
King garden room with en suite bathroom, sleeps 2

Reviews

10 out of 10
Exceptional
6 bedrooms5 bathroomsSleeps 163400 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
Windham, NY
  • Place, Catskill State Park
    ‪1 min walk‬
  • Place, Windham Mountain Resort
    ‪15 min walk‬
  • Place, Hunter Mountain
    ‪18 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪51 min drive‬

Rooms & beds

6 bedrooms (sleeps 16)

1st Floor Master

1 King Bed

Bedroom 5

2 Single Bunk Beds

Bunk Room 1

2 Single Bunk Beds

Daybed/Office

2 Single Beds

Garden Bedroom 1

1 King Bed

Garden Bedroom 2

1 King Bed

5 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Separate dining area
Outdoor play area
Garden

About this property

Chalet nestled right in Windham Mountain's quiet beauty-private access to trails


*WELCOMING INQUIRIES FOR SKI SEASON 2025-26, and SUMMER-FALL GUESTS!!!**

Perfect Windham Mountain slope side chalet. Short walk to slopes in winter and biking/hiking trails in summer. This spacious 3,400ft chalet is nestled within Windham Mountain’s quiet wooded beauty with its own seasonal babbling brook running beside it, phenomenal views from many rooms and large deck space. 3 king bedrooms each with an en suite bathroom, 2 bunk bedrooms (4 bunk beds per room, with custom 'crib' rails on 2 beds), and 1 trundle bedroom (2 single mattresses). 2 stone fireplaces, living room, dining room with seating for 14 (dining table seats 12 / kitchen breakfast bar seats 2), den, game room, ski gear room, 5 bathrooms total. Hot tub on 2nd deck. Wi-fi throughout the house, Smart TVs in king bedrooms, living room, den, and game room, also DVD player in living room. Lovingly decorated throughout, this is a special house for your stay in Windham, with all it has to offer, including a few minutes drive to the center of town with shops and restaurants, the Windham Country Club, the Windham Hiking Trail, and so many outdoor destinations nearby.

Prior rented privately - references are available.

Ask about additional services available:
Pantry stocking
Cleaning services
Ski ticketing
Equipment rental pick-up/drop-off
Spa appointments
In home yoga or massage
Private chef / catering
Babysitting referrals
Area information.

Add dates for prices

Amenities

Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Exterior
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (109 reviews)
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
default

Children

Children allowed: ages 0–17
default

Events

Events allowed: family gatherings and birthday parties
default

Pets

No pets allowed, service animals permitted
default

Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load the dishwasher
Remove personal items and remove leftover food and drinks
Turn off the lights, lock the doors and return the keys
Please bag garbage tightly and leave it in the kitchen.
Turn off AC's and/or turn the heat back to 50, please.
Leave key on counter
Failure to complete these may result in a negative review from the host.
Parking: Please park your cars in the parking area at the end of the street on the right
Securely bag garbage and leave in kitchen.
Check Out: please make sure lights are off, windows closed, and heat returned to 50 or AC's off.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings and birthday parties) are allowed on site. Maximum attendees: 25
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Windham

Located in Windham, this chalet is in the mountains. Windham Mountain Resort and Hunter Mountain are worth checking out if an activity is on the agenda. Travelling with kids? Consider Mountain Top Arboretum and Zoom Flume. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Chalets in WindhamOpens in a new window
Map
Windham, NY

What's nearby

  • Catskill State Park - 1 min walk - 0.0 km
  • Windham Mountain Resort - 15 min walk - 1.3 km
  • Hunter Mountain - 18 min drive - 21.3 km
  • Catskill Mountains - 36 min drive - 47.5 km
  • Belleayre Mountain Ski Center - 44 min drive - 59.9 km

Getting around

  • Hudson, NY (HCC-Columbia County) - 55 min drive

Restaurants

  • ‪Chicken Run - ‬6 min drive
  • ‪Catskill Mountain Country Store - Windham - ‬6 min drive
  • ‪Higher Grounds Coffee Shop - ‬7 min drive
  • ‪Babblers - ‬7 min drive
  • ‪Windham Diner - ‬6 min drive

Frequently asked questions

Is Chalet nestled right in Windham Mountain's quiet beauty-private access to trails pet-friendly?

No, only service animals are welcome at the property.

How much does it cost to stay at Chalet nestled right in Windham Mountain's quiet beauty-private access to trails?

As of 11 Mar, 2026, prices found for a 1-night stay for 2 adults at Chalet nestled right in Windham Mountain's quiet beauty-private access to trails on 9 Apr, 2026 start from S$820, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Chalet nestled right in Windham Mountain's quiet beauty-private access to trails?

On-site parking is available at the property.

What time is check-in at Chalet nestled right in Windham Mountain's quiet beauty-private access to trails?

Check-in begins at 3:00 PM.

What time is check-out at Chalet nestled right in Windham Mountain's quiet beauty-private access to trails?

Checkout is at 11:00 AM.

Where is Chalet nestled right in Windham Mountain's quiet beauty-private access to trails located?

Located in the mountains, this ski-in/ski-out chalet in Windham is within 1 mile (2 km) of Catskill State Park and Windham Mountain Resort, and is convenient for winter sports, such as cross-country skiing and sledging. Windham Country Club is 1.8 mi (2.9 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 21 out of 22 reviews
Rating 8 - Good. 1 out of 22 reviews
Rating 6 - Okay. 0 out of 22 reviews
Rating 4 - Poor. 0 out of 22 reviews
Rating 2 - Terrible. 0 out of 22 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

maureen b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house. Didn’t love carpeting in the bathrooms
Stayed 3 nights in Oct 2025

10/10 Excellent

Sarah W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Incredible view

We had a great stay— easy check-in, tons of room to spread out in the house, and omg the views!!!
Stayed 2 nights in May 2025

10/10 Excellent

TSERING L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Outstanding Family Staycation

Our Family and friends had an amazing stay! The rooms were very clean when we first arrived, and the kids absolutely loved the hot tub. The owner, Ali, was kind and easy to contact.! It was such a pleasure to stay here, and we hope to come again soon!
Stayed 2 nights in Jul 2025

10/10 Excellent

Robert W.

Liked: Cleanliness, check-in, communication, listing accuracy

Extraordinary ciews

Excellent property. Everything as promised.
Stayed 4 nights in Aug 2025

10/10 Excellent

NATHAN M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family reunion

Wonderful indoor and outdoor spaces in a gorgeous and classy environment. Ample kitchen, nice bedrooms and bathrooms. Great place to stay and relax. Host was responsive, kind and generous. Would highly recommend.
Stayed 4 nights in Jun 2025

10/10 Excellent

Eric L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location!

Ali was an awesome host and her property was perfect for our friends and family. We enjoyed out stay and would absolutely recommend this property to others.
Stayed 3 nights in Jul 2021

10/10 Excellent

Lawrence M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ski weekend with dads and sons

Couldn't have been a better place to accommodate the large group of us. It was comfy, large, well equiped and stocked. Prefect location and tons of fun things. We'll definitely be back there next year....
Stayed 2 nights in Feb 2025

8/10 Good

Chris D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family wedding weekend

Property was very good for the six of us that were attending a family wedding in Windham. Views from the back deck during peak fall foliage days were spectacular.
Stayed 2 nights in Oct 2024

10/10 Excellent

Juan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A lovely property with a caring manager

Alice is a great host, she was super responsive and always willing to help. The house is what you see on the pictures and even better. While it is a bit dated it has all the necessary to enjoy the Windham ski resort, and generally life in Upstate NY. The views are outstanding, you are literally in the mountain (never felt closer to one than on this trip!). I would totally book here again!
Stayed 8 nights in Dec 2024

10/10 Excellent

Courtney C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Huge fun house

Great house for a big group. The pool table was added fun for everyone. The younger ones loved the hot tub. Plenty of room for everyone to spread out. Our group was age 13 and up. We were 10 people but easily could’ve been many more. The house is on the older side, but it’s perfect for a Windham ski week. I would definitely rent it again. Host was super easy to get in touch with, although we didn’t need much as we frequent Windham mountain every winter.
Stayed 4 nights in Dec 2022

10/10 Excellent

Jennifer H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Windham!

Our large group of 13--3 families with 6 adults and 7 children ranging in age from 7-15--had an absolute blast at this house! From start to finish, the host, Ali, was so lovely and easy to communicate with. The house was exactly as listed with all of the wonderful features--gorgeous view and setting right at the mountain, plenty of comfortable space to sleep and spread out, large common room, pool table, large hot tub, and plenty of linens and towels. The kitchen was well stocked for cooking with really nice cookware and nice extras. Everything was clean and well organized. We would be delighted to stay again.
Stayed 2 nights in Oct 2021

10/10 Excellent

Amy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Summer Getaway

My husband and I rented this house for five nights. It was way bigger than we needed, but the view in the photos looked amazing, so we booked it. It did not disappoint! The view from the deck was breathtaking! My favorite part of the day was having coffee on the deck in the morning, breathing in fresh mountain air, and just staring out at the view ahead. Ali, the property manager, was wonderful. She met us at the house for check-in, which was super-easy, and responded quickly to any questions we had. The location was fantastic - right next to Windham ski resort, and about a five minute drive into town. The house was clean (although the living room carpet could use a cleaning in spots), and very comfortable. We basically used just the upstairs, except for when our son came for a couple of nights, and stayed in one of the large bedrooms downstairs (we joked that the house was so large, his bedroom was in another zip code). The upstairs bedroom that we used was spacious, and the bed was very comfortable. There was a large, walk-in closet, and a big dresser, providing lots of room to unpack. We did not do much cooking, but the kitchen was extremely well stocked, and the appliances were in excellent condition. The game room downstairs was an added bonus, with a pool table and jukebox. One suggestion if traveling with small children and/or pets: bring a gate to block off the staircase. We were glad we brought one to keep our dog from wandering all over the house. We enjoyed our stay tremendously, and would highly recommend this house!
Stayed 5 nights in Jul 2022

10/10 Excellent

Emanuel S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great House at Windham Mt

Recently, my wife and I rented this house for a multi-generational family getaway. The house met or exceeded our expectations in every way. First of all, size: The house features 3 King Bed master bedrooms, each with its own private bathroom. There are another 3 more kid-sized bedrooms (two of which have 4 bunkbeds each), plus another couple of bathrooms. There are two living rooms and a pool table/game room (with a working juke box). The house is spread out in such a way that there are separate bedroom/bathroom "pods," affording unexpected areas of privacy for different groups sharing the house. My daughter and son-in-law and their young kids had their own private area of the house. My other daughter had her own private area, etc. The house would therefore be ideal, for example, for three couples sharing the rental. There's a nice sized kitchen, a big dining area and a large deck. We ate meals both indoors and out, as the weather dictated. We also sat around the fire pit, toasting marshmallows, and enjoyed our soaks in the hot tub after a day of hiking. The house was well stocked with tons of large towels, linens, and other basic necessities. All in all, the house served our needs perfectly. Ali, our hostess, was a pleasure to deal with--responsive and helpful in every conceivable way. We'd rent the house again in a heartbeat. One small caveat: I wouldn't want to be trying to find the house for the first time in the dark. We made it our business to arrive during daylight and were happy we made that decision.
Stayed 5 nights in Jun 2022

10/10 Excellent

John P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Thanksgiving weekend

Perfect house for our family of 15. Kids had plenty of sleeping options and lots of places to hang out amongst themselves. The adult enjoyed the dining and living areas. Great location. Amazing views. Great town with restaurant and bar bar options.
Stayed 4 nights in Nov 2022

10/10 Excellent

Brendan P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful stay

Absolutely wonderful home with a gorgeous view. Host was very responsive and incredibly nice.
Stayed 2 nights in Aug 2022

10/10 Excellent

Henry G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another great stay!

Our stay in Windam was another great weekend trip for my family. Ali is a tremendous host, the house is very clean and her responses to a couple questions were immediate. We will surely be staying there again in the future.
Stayed 2 nights in Jul 2022

10/10 Excellent

Rick T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing!!!

I would recommend this home for your next Windham vacation. We travelled with our three children (20,22,23) and some of their friends. The house was plenty big enough for all of us with room to spare. We enjoyed cooking dinners at home, admired the beautiful views out of the large windows throughout the house, soaked in the hot tub after a day on the slopes, and had some fun family time in the game room with the pool table! Aly was an amazing host and quickly responded to any questions we had! Definitely will return!!
Stayed 4 nights in Dec 2021

10/10 Excellent

Jessica B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Thanksgiving getaway

Me and my friends had a great time at this property. The house is beautiful, cozy and clean. The view from the terrace is amazing and the location is great, easy to go on hikes or to ski. The owners are extremely helpful and responsive to messages. We loved our stay would definitely come back!
Stayed 3 nights in Nov 2021

10/10 Excellent

Surie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful weekend gateway

We had a great time, the quietness, tranquility, peace of mind, and the beautiful view up here is so amazing, superb communication with Ali was very amazing!!! Thanks loads for everything!!!
Stayed 3 nights in Aug 2021

10/10 Excellent

Henry G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

I would give this listing 10 stars if I could

Our stay was nothing short of amazing. Ali was a GREAT host and was quick to respond to questions. Check-in was a breeze and the house was immaculate. Everyone was taken in by the breath taking view from the deck the minute they walked in. The house is spacious and well decorated with everything you need to make your stay fun and enjoyable. We booked this house for our first family reunion in decades. We laughed, reminisced and cried a bit and will be forever grateful to Ali for providing the perfect setting for us. And by the way – if you don’t spend some time shooting pool and listening to the old time juke box, you just don’t know how to have fun!
Stayed 2 nights in Jul 2021

10/10 Excellent

RAKESH M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Hospitality and Great Place

Ali was a great host! Responded very quickly, and was very accommodating to our needs/requests. Check-in instructions were super detailed and helpful. The place was very clean and well stocked. We could not have asked for a better location. Overall a wonderful place; we would stay here again easily!
Stayed 3 nights in Jul 2021

10/10 Excellent

Muhammad A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic place!

Loved the place! it was super clean Ali was awesome and we have everything we needed. Would have loved it even more if the weather cooperated. Would love to go back there
Stayed 3 nights in May 2021

About the host

Hosted by Ali O'Brien

Host profile image
I manage and direct rent vacation homes in Windham, NY. I am available during your stay to help with guest's needs (pantry stocking, wood delivery, lift tickets and lessons). Please contact me with any requests and I will do my best to accommodate all your family's requests.

Why they chose this property

Unique mountainside chalet is situated on 2 lots offering space, privacy. Layout of the house is perfectly set up to host multi-family with private living spaces sharing common areas.

What makes this property unique

Mountainside, spacious, breathtaking views, close to shops, spa, restaurants, hiking, skiing, snowboarding, mountain biking, snow tubing, area lakes, horseback riding, water park, mini golf, vineyard.

Languages:

English
Tell us how we can improve our siteShare feedback

Hotels

Holiday Rentals