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Compare 28 Chalets in Middleburgh with updated reviews, rates, and availability.

Beautiful Chalet, mins to Hunter/Windham slopes
10.0 out of 10, Exceptional, (7)
"We booked our house for a mini family reunion and this house was perfect. The house was clean and well stocked, the beds were very comfortable and the setting of the house was calming and peaceful. We would definitely book again"
Beautiful Chalet, mins to Hunter/Windham slopes
Charming chalet with 5 bedrooms and WiFi, fitness room in peaceful Roxbury
2.0 star property
Charming chalet with 5 bedrooms and WiFi, fitness room in peaceful Roxbury
Charming Log Chalet w/ huge deck, pool & bonus garage loft on 17 secluded acres
10.0 out of 10, Exceptional, (19)
"We had a great time! The house and view of the mountains was beautiful and was exactly what we expected. Joshua was a great host and responded quickly to questions. Highly recommend!"
Charming Log Chalet w/ huge deck, pool & bonus garage loft on 17 secluded acres
Chalet w/ OUTDOOR TV & HOT TUB; POOL, fire pit, pool table, trail & playground!
10.0 out of 10, Exceptional, (17)
"Great location, lots of local hiking, beautiful area. House had a ton to offer for the kids, but we spent most of the time outside! Hosts very quick to respond and included thoughtful extras for our dogs. Highly recommend!"
Chalet w/ OUTDOOR TV & HOT TUB; POOL, fire pit, pool table, trail & playground!
Secluded Chalet in the Northern Catskills with FIBER Internet and EV hookup
10.0 out of 10, Exceptional, (6)
"We like to meet up with some friends from Maine about once a year near the halfway point between us. Ray's Chalet is a great place to chill out and relax with friends and family. The Chalet is very clean and there's plenty of room for everybody. Great for grilling, lawn games, bonfires, etc. Ray adds a lot of nice touches as well, but I won't ruin the surprises for you. (BTW--Ray, thanks for the spare toothbrush set up! Saved our lives when we had to bring the kids at the last minute due to...
Secluded Chalet in the Northern Catskills with FIBER Internet and EV hookup
BEAUTIFULLY SECLUDED- Spring, Summer Getaway w PRIVATE Indoor Pool
8.4 out of 10, Very Good, (51)
"Overall, nice private location. House was not as clean as it could have been . Owner responsive to messages and requests!"
BEAUTIFULLY SECLUDED- Spring, Summer Getaway w PRIVATE Indoor Pool
🏔Windham🏔 - Hot Tub🛀Game Room🕹Fire Pit🔥Ski Views 👀
10.0 out of 10, Exceptional, (21)
"We had a great weekend at the Manor. The game room was excellent and provided entertainment for everyone."
🏔Windham🏔 - Hot Tub🛀Game Room🕹Fire Pit🔥Ski Views 👀
Cozy Country Cabin with Amazing Mountain Farm Views and Nearby Lake! EV-King Bed
10.0 out of 10, Exceptional, (8)
"Relaxing remote location with lovely views of local farmland. Perfect wedding weekend getaway with our adult kids."
The price is SAR 2,248
SAR 4,838 total
includes taxes & fees
24 Sep - 25 Sep
Cozy Country Cabin with Amazing Mountain Farm Views and Nearby Lake! EV-King Bed
Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces
Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces
Never Lonesome Hunter: Smart 4bd Getaway near Mtn
10.0 out of 10, Exceptional, (2)
"Nice little house to stay in if you're looking to spend time in the mountains. It's old, for sure, but it was comfortable and conveniently located. Hosts were great about communicating. It was a nice, chill vacation."
Never Lonesome Hunter: Smart 4bd Getaway near Mtn
Windham Immaculate Ski Chalet with Awesome Fire Pit.
9.8 out of 10, Exceptional, (7)
"We are a big family with 4 kids between 6 and 17 year old. The house is the perfect size for us! It's very clean and the linens are very comfortable. The location is so convenient! Less than 10 min drive to Windham ski resort. Peter is very responsive and accommodating! We had a great time!"
Windham Immaculate Ski Chalet with Awesome Fire Pit.
Chalet near Windham w/ hot tub
Chalet near Windham w/ hot tub
5 Star Gorgeous Cliffside Chalet with Panoramic Views
10.0 out of 10, Exceptional, (1)
"This home is a beautiful refuge. Lots of windows offer breathtaking views and colorful sunsets. The house is well-furnished and equipped. The owner was accessible and invested in our comfort in his home. Renters should understand, however, that the primary bedroom is in a loft, with no shades or drapes to cover the windows. If all that light/exposure would be a sleep issue for other renters, they should bring a good sleep mask. "
5 Star Gorgeous Cliffside Chalet with Panoramic Views
Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace
10.0 out of 10, Exceptional, (2)
"We had a great time staying at this house for the weekend. Everything was awesome and so thoughtfully put together. The attention to details made our experience even more special. The hot tub with the view and car charger were welcome amentities. I highly recommend this place!"
Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace
🍂 Fall Escape! Stunning 3BR/3BA Condo on Hunter Mountain - Book Now! 🍁
🍂 Fall Escape! Stunning 3BR/3BA Condo on Hunter Mountain - Book Now! 🍁
Wooded Lakefront Oasis w/ Kayaks, Game room & Lakeside Fire Ring
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay! The house has everything you could possibly need for a fun weekend or week! So much to do between the lake and the games! We paddleboated, fished, played badminton, ping pong and cornhole! The host is very generous with her house, and just wants everyone to have a great time at her place! There are two loungers and four adirondack chairs down by the lake (not pictured) which is very nice! The house has everything you need to make meals if you don't want to go out. There...
Wooded Lakefront Oasis w/ Kayaks, Game room & Lakeside Fire Ring
cozy retreat with modern amenties
2.0 star property
cozy retreat with modern amenties
Family friendly home with a large yard
Family friendly home with a large yard
Luxurious 3BR/2BA Chalet w/ Panoramic Views Near Windham Mountain on 22+ Acres
Luxurious 3BR/2BA Chalet w/ Panoramic Views Near Windham Mountain on 22+ Acres
Mountain-Top Getaway with Hot Tub and Game Room!
Mountain-Top Getaway with Hot Tub and Game Room!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Middleburgh

Tuscan Year Round Beauty - Pickleball Court
10.0 out of 10, Exceptional, (94)
"Rick was an amazing host and the property exceeded expectations and the views are amazing. Well worth it. "
Tuscan Year Round Beauty - Pickleball Court
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
10.0 out of 10, Exceptional, (85)
"Each year we go on vacation with our daughter, son in law and his family. We are a group of 12 and loved this lake house. We all want to make this our yearly trip. Great place"
The price is SAR 1,501
SAR 2,661 total
includes taxes & fees
14 Oct - 15 Oct
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
Located in the beautiful Heldebergs, This is a cute little house you will love.
10.0 out of 10, Exceptional, (74)
"Excellent accommodations, beautiful lake & woods, great hosts!"
Located in the beautiful Heldebergs, This is a cute little house you will love.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.