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Compare 30 Chalets in Middleburgh with updated reviews, rates, and availability.

Beautiful Chalet, mins to Hunter/Windham slopes

10.0 out of 10, Exceptional, (11)
"Really lovely house with a beautiful view."
Beautiful Chalet, mins to Hunter/Windham slopes

COZY WINTER SKI Getaway w Fireplace & PRIVATE Indoor Pool! 5 mins to Hunter Mtn!

8.4 out of 10, Very Good, (55)
"Perfect for our ski/snowboarding getaway! Very secluded location. "
COZY WINTER SKI Getaway w Fireplace & PRIVATE Indoor Pool! 5 mins to Hunter Mtn!

Luxury 3300 sqft Ski & Golf Chalet,2 fireplaces & Firepit.5 min from Windham Ski

10.0 out of 10, Exceptional, (2)
"We love the cabin and the location is even better. Plenty of room for two families and the property is very well kept. We would definitely stay again. Thanks!"
The price is AED 1,785
AED 3,614 total
includes taxes & fees
4 Feb - 5 Feb
Luxury 3300 sqft Ski & Golf Chalet,2 fireplaces & Firepit.5 min from Windham Ski

Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces

10.0 out of 10, Exceptional, (2)
"Great location and decent building! Amina is such a nice host and a huge plus! She was accommodating and answered all our requests and questions promptly and solved issues in a timely manner. The only thing we would like to remind the other guest is that please bring lots and lots of bottled water since the tap water is slimy and you need bottle water for both cooking and drinking."
Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces

Beautiful Windham Chalet 2 minutes to Town and the Mountain

3.0 star property
Beautiful Windham Chalet 2 minutes to Town and the Mountain

Luxurious & Serene 2 Acre Mountain Cabin Retreat - 3 Bedrooms - Fully stocked

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had such an amazing time at this house. It was extremely clean and had everything that we needed to have the perfect evening. The property is super nice and definitely took advantage of the gazebo overlooking the pond. The location is great and it is very close to both Hunter and Windham. We will definitely be coming back"
Luxurious & Serene 2 Acre Mountain Cabin Retreat - 3 Bedrooms - Fully stocked

Rustic Mountain view Cabin 5 mins to Ski Area!

10.0 out of 10, Exceptional, (4)
"Cozy great view close to the mountain"
The price is AED 1,833
AED 2,075 total
includes taxes & fees
17 Feb - 18 Feb
Rustic Mountain view Cabin 5 mins to Ski Area!

Chalet w/Covered HOT TUB & OUTDOOR TV; fire pit, pool table, trail & playground!

10.0 out of 10, Exceptional, (18)
"We stayed for Christmas to be close to family ! Very cozy yet spacious ! Kids loved the pool table and hot tub . "
Chalet w/Covered HOT TUB & OUTDOOR TV; 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

Charming chalet with 5 bedrooms and WiFi, fitness room in peaceful Roxbury

2.0 star property
8.0 out of 10, Very Good, (2)
"Nice living and dining space. Plenty of room to spread out. with 3 bedrooms up and 2 down you can. A few of the outlets are not currently working and there may be a yellowjacket nest that needs to be dealt with near the back deck. Outside of that I would rent it again "
Charming chalet with 5 bedrooms and WiFi, fitness room in peaceful Roxbury

🏔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 👀

Modern Rustic Log Chalet w/ mtn views, pool & bonus loft on 17 secluded acres

10.0 out of 10, Exceptional, (21)
"Amazing property with excellent hosts.Our whole family loved!!!"
Modern Rustic Log Chalet w/ mtn views, pool & bonus loft on 17 secluded acres

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."
Cozy Country Cabin with Amazing Mountain Farm Views and Nearby Lake! EV-King Bed

cozy retreat with modern amenties

2.0 star property
The price is AED 799
AED 1,138 total
includes taxes & fees
4 Feb - 5 Feb
cozy retreat with modern amenties

Private Chalet less than 1 mile to Ski Resort

9.6 out of 10, Exceptional, (5)
"Really great property for our family of four (two young kids) and our late December trip to Hunter Mountain. The kids loved playing in the loft and we had ample space for all in the kitchen and family room. Incredibly easy ride to the mountain each morning. Property is also set back a bit from the road which makes it feel a bit more private. Would definitely stay again."
Private Chalet less than 1 mile to Ski Resort

Lakefront Chalet w/ game room 25 min. from skiing & snow tubing. Pet-friendly!

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...
The price is AED 617
AED 1,342 total
includes taxes & fees
5 Feb - 6 Feb
Lakefront Chalet w/ game room 25 min. from skiing & snow tubing. Pet-friendly!

Windham Immaculate Ski Chalet with Awesome Fire Pit.

9.8 out of 10, Exceptional, (8)
"Our family really enjoyed this home over a long fall weekend. The home is immaculate with plenty of space/bathrooms for my 3 adult kids and my husband and I. The kitchen is well stocked with everything needed. Plenty of paper products, soaps, basic spices. I appreciated how clean it was. Communication with the host was great, very responsive. We thoroughly enjoyed both the indoor fireplace and outdoor fire pit. Beautiful area for long hikes and to enjoy everything Windham has to offer. Would...
Windham Immaculate Ski Chalet with Awesome Fire Pit.

🍂 Fall Escape! Stunning 3BR/3BA Condo on Hunter Mountain - Book Now! 🍁

🍂 Fall Escape! Stunning 3BR/3BA Condo on Hunter Mountain - Book Now! 🍁

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

Chalet near Windham w/ hot tub

4.0 out of 10, (1)
"We stayed here on a ski trip with friends. The property manager forgot to have the house cleaned before we came, and as a result the cleaners arrived when we arrived to check in. We wanted to eat dinner at the house but were forced to go out for dinner since it was not ready. The house was missing any blinds in 2 of the three main bedrooms (a big deal for parents with kids who wake up with the sun), and the tv did not work. The main toilet was brown and disgusting and master toilet was not...
Chalet near Windham w/ hot tub
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

True Ski On - Ski Off Four Seasons Luxury Mountain Retreat!

2.0 star property
9.8 out of 10, Exceptional, (28)
"Great place to stay for skiing hunter mt and would do it again ….thanks "
The price is AED 577
AED 995 total
includes taxes & fees
4 Feb - 5 Feb
True Ski On - Ski Off Four Seasons Luxury Mountain Retreat!

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

10.0 out of 10, Exceptional, (148)
"We went with 3 families (kids 4-14) and had the best time !! Great house for a group. We were 18 total. Awesome location. The kids loved playing in the snow and visiting with the cows! The grounds were really beautiful. The house had plenty of room. The bunk rooms were awesome for kids. Upstairs master has a tiny room a one single bed off of it, perfect for a toddler or baby. Two living rooms for multiple sports game watching. Short drive to the mountain and restaurants. We even brought food...
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (98)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court
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.