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Compare 25 Chalets in Callicoon with updated reviews, rates, and availability.

Lake Wallenpaupack, Poconos Hilltop Haven with children’s playarea and 5 kayaks!

10.0 out of 10, Exceptional, (25)
"This vrbo was the most well appointed one I have ever stayed in. They had everything you could need in the kitchen and an incredible amount of toys for the children to play with. "
Lake Wallenpaupack, Poconos Hilltop Haven with children’s playarea and 5 kayaks!

Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

9.6 out of 10, Exceptional, (106)
"My husband and I stayed for our anniversary week in early September and the place could not have been more perfect! The photos in the listening don't do the property justice. The lake was spectacular. Perfect location with rustic cabin charm!"
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

Falling Waters Chalet ★ Great for Groups ★ Fire Pit ★ Lake ★ Masthope

10.0 out of 10, Exceptional, (17)
"Our second visit this year! Had a great time! Enjoy the house & how large, yet cozy it is. Maybe we will be back for one more weekend in March! Thank you! "
Falling Waters Chalet ★ Great for Groups ★ Fire Pit ★ Lake ★ Masthope

Cozy Chalet in the woods with Arcades, Fire pit, Lake, Pools & Ski Lifts

9.6 out of 10, Exceptional, (10)
"The house was as pretty in person as it looked online! It was super cozy and had a warm inviting feel to it. The owner was very accommodating and responded quickly to my inquiries. We look forward to renting this house again in the summer to enjoy the patio and outdoor seating. "
Cozy Chalet in the woods with Arcades, Fire pit, Lake, Pools & Ski Lifts

The Lookout ★ Lake ★ Masthope ★ Firepit ★ Shuffleboard

10.0 out of 10, Exceptional, (13)
"House was as advertised, good location, plenty of room, generally clean. Basement living space smelled a bit off, but we didn’t need to use it so we stayed out. EV “charger” is just a NEMA outlet, you must bring your own charging cable to use. Would rent again."
The Lookout ★ Lake ★ Masthope ★ Firepit ★ Shuffleboard

Masthope modern log-cabin sided retreat!

9.8 out of 10, Exceptional, (111)
"Second time staying at this property. Great location and close proximity to all amenities. Very relaxing getaway. Will be back next year. "
Masthope modern log-cabin sided retreat!

Masthope Ski Chalet | 4 Bedroom | Firepit & Kayaks

2.0 star property
6.0 out of 10, (1)
"First off, CJ is one of the best. He is great about communicating everything you need to know and then some. And he is super responsive. The house was excellent and exactly as advertised. We loved it and will be back! Thank you CJ!"
Masthope Ski Chalet | 4 Bedroom | Firepit & Kayaks

The Chalet - Rustic Retreat

9.4 out of 10, Exceptional, (6)
"Hubby and I wanted a cute getaway for thanksgiving weekend, and this little cabin was perfect. Secluded but still close enough to civilization. The hot tub was wonderful. We unfortunately never got to use the fire pit - just a bit too cold out for us. Space is great. There is a pretty close neighbor, but it didn’t impact our stay at all, and we basically forgot the house was there. The road to the cabin is unpaved so 4WD is probably a good idea. Very cute place "
The price is AED 606
AED 1,270 total
includes taxes & fees
24 Feb - 25 Feb
The Chalet - Rustic Retreat

Luxurious 4Bd King size bed, HotTub,5 min to Skiing Masthope, pools lake.retreat

9.8 out of 10, Exceptional, (9)
"House was set up perfect for 2 familys and teenage kid.."
Luxurious 4Bd King size bed, HotTub,5 min to Skiing Masthope, pools lake.retreat

Giant chalet with private lake access. Hot tub. pet friendly. ultimate game room

10.0 out of 10, Exceptional, (16)
"Quirky, spacious house with plenty of bedrooms and several kitchens/sinks with the in law apartment. Big table for eating and games by a wood stove. Game room is great for kids (and nerf gun battles). We were there in several snow and ice storms but managed to squeeze in some hot tub time. Communication with the property manager was excellent. "
Giant chalet with private lake access. Hot tub. pet friendly. ultimate game room

Catskills Lakefront Escape with Hot Tub

10.0 out of 10, Exceptional, (17)
"Everyone had a place to sleep! Very clean! Great hot tub! "
Catskills Lakefront Escape with Hot Tub

Luxury 4BR Chalet-5 Mins. to Pool/Lake/Ski-Game Room in Basement

10.0 out of 10, Exceptional, (73)
"Family trip. We had a great time. Kids loved the house the and all the games. 5 stars."
Luxury 4BR Chalet-5 Mins. to Pool/Lake/Ski-Game Room in Basement

Bella Vista Chalet Poconos -Four Season Resort/Lake/Pool/Ski/Horseback-riding

9.8 out of 10, Exceptional, (6)
"We had to add extra day to booking and owner was very accommodating. Responded quickly to all requests. All simple issues like regulating heat and finding firewood. Great modern appliances. Central location with all sorts of amenities on site. We will rent again same time next year to visit friends in area."
Bella Vista Chalet Poconos -Four Season Resort/Lake/Pool/Ski/Horseback-riding

Lake House in the Summer, Ski Chalet in the Winter, Pet Friendly!

9.6 out of 10, Exceptional, (5)
"When we arrived at Big Bear Chalet we couldn’t believe the spaciousness as well as cleanliness of this home. The description was spot on! Nothing was left out, every amenity listed was in the home and then some! We were a total of 6 adults, a toddler and a baby as well as my daughter’s beagle. Loved every moment and hope to be back next year. Even the weather didn’t deter us from having a good time. "
Lake House in the Summer, Ski Chalet in the Winter, Pet Friendly!

Modern Chalet with Hot Tub and Lake Access

10.0 out of 10, Exceptional, (3)
"Escaped the city for a five star weekend. The house was fully equipped for preparing group meals, offering plenty of space to enjoy them together. StayBettr was perfectly communicative and provides a guide with everything you need to prepare for your stay. We relaxed in the hot tub and bonded over a private, virtual @journalingclasses session. Don’t forget to stop by Tilly’s diner (15min) drive away for a delicious breakfast or lunch with the most wonderful waitstaff. We hope to come back again!"
Modern Chalet with Hot Tub and Lake Access

3-bedroom chalet just 13 minutes drive to Bethel Woods

3-bedroom chalet just 13 minutes drive to Bethel Woods

Cozy Catskills Chalet

10.0 out of 10, Exceptional, (2)
"I want to say that this was a terrible experience to keep this place available to us in the future, but it would be a complete lie. Immaculately clean house, comfortable beds, and a convenient location will bring us back to this house for sure. Thanks for sharing it with us!"
Cozy Catskills Chalet

Welcome to beautiful Masthope Mountain Community in the Poconos!

Welcome to beautiful Masthope Mountain Community in the Poconos!

Cozy, Tranquil A-Frame Oasis

10.0 out of 10, Exceptional, (1)
"A beautiful, peaceful and well-appointed home. We loved staying here. Great location close to Bethel woods."
Cozy, Tranquil A-Frame Oasis

Relaxing retreat - Lake - HotTub - Firepit - Gameroom - Pet Friendly - sleeps 10

10.0 out of 10, Exceptional, (1)
"This comfortable, cozy, 4 BR home is nicely tucked into the woods. Plenty of space to spread out for adults and kids, with a finished basement. Outside there is a fire pit, and jacuzzi/hot tub. House is well stocked for cooking supplies and tools, and quiet at night. Close to Livingston Manor Main Street (7min), Roscoe Main Street (10min) and only 1/2 mile away from Arnold House. Host was super responsive and a pleasure to work with. Would love to come back !"
Relaxing retreat - Lake - HotTub - Firepit - Gameroom - Pet Friendly - sleeps 10
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 Callicoon

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (70)
"This beautiful getaway was just what we needed. Fresh air, nature, and a gorgeous home. Already planning our next trip back..."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (144)
"We just spent our first Valentines day together at this beautiful cabin and I loved the quiet and beautiful surroundings. I plan to come back in the future. Thank you so much "
The price is AED 389
AED 1,157 total
includes taxes & fees
24 Feb - 25 Feb
Handcrafted Riverfront Cabin on 10 acres

Postcard Cabins Western Catskills

2.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent stay. Special thanks to Sissy who met us while check out who was very kind to take care of stuffs we wanted to clear that helped us expedite our check out."
The price is AED 413
AED 455 total
includes taxes & fees
12 Mar - 13 Mar
Postcard Cabins Western Catskills
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.