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Compare 407 Vacation Homes in Callicoon with updated reviews, rates, and availability.

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

9.0 out of 10, Wonderful, (73)
"We had an amazing stay at this property! Everything was exactly as described—clean, comfortable, and beautifully maintained. It felt like a true home away from home. The location was perfect, and all the amenities were thoughtfully provided.What really stood out was how smooth and stress-free the whole process was. Communication with the owner was excellent from start to finish—quick responses, clear instructions, and super helpful throughout. It made the entire experience even better.Highly...
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

In the cloud ~your cozy lake house

9.6 out of 10, Exceptional, (86)
"We enjoyed our stay at the lake house. Clean and great access to the lake. Two thumbs up!"
The price is SAR 705
SAR 1,320 total
includes taxes & fees
1 May - 2 May
In the cloud ~your cozy lake house

Sun Drenched Lakefront Cove

9.0 out of 10, Wonderful, (18)
"The accommodations were beautiful, comfortable and clean. All the ladies felt pampered living in the lap of luxury.The hosts responded to any questions in a timely manner.The location is stunning. Right on the lake with beautiful views and quiet roads for walks.Highly recommend"
Sun Drenched Lakefront Cove

Private Indoor Pool - Hot Tub - 2 Fishing Ponds - 33 Acres

9.6 out of 10, Exceptional, (28)
"Host was very responsive and the house was fun and served its purpose. Overall great experience. "
Private Indoor Pool - Hot Tub - 2 Fishing Ponds - 33 Acres

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (30)
"The house was great. Clean, cozy and spacious. There was room for everyone in our large group snowboarding at elk mountain (a little over 20 min away). "
Breathtaking 44+ Acre Country Estate

Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

10.0 out of 10, Exceptional, (118)
"Had a great stay. Very peaceful. "
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

Masthope Mountain Hideaway walking distance to the lake and 8 min to ski lodge

10.0 out of 10, Exceptional, (7)
"We’ve been going for President’s Day weekend for years, meeting friends and their kids, who now bring their own kids.133 Rainbow is a great home. Clean and bright, it’s spacious yet cozy. We had a wonderful visit."
Masthope Mountain Hideaway walking distance to the lake and 8 min to ski lodge

Spacious 5 BDRM Masthope Chalet with Private Movie Theater & AWESOME Game Room

10.0 out of 10, Exceptional, (1)
"I can’t say enough positive things about this home! The way each room was perfectly suited for a specific purpose: the basement was all for kids and fun zone, the living room has the MOST comfy giant couch ever - perfect for watching TV together as a family, the kitchen is spacious for cooking and serving meals, and the bar had disco lights which added a pop of color and fun to our evenings, finally the deck was comfy and the fire pit was perfect for late night s’mores! We had a large group of...
Spacious 5 BDRM Masthope Chalet with Private Movie Theater & AWESOME Game Room

Charming 3-bedroom house with HUGE yard in Livingston Manor

Charming 3-bedroom house with HUGE yard in Livingston Manor

Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

8.0 out of 10, Very Good, (20)
"Nothing negative to say really. Booked this house for 20 guests and it fit us all comfortably. Everything was clean and loved the way this house was layed out. Lots of room and many things to do even inside the house. Huge backyard. Host was very kind. Not many things like paper towel, toilet paper, garbage bags for 4 days with 20 guests as well as no washer and dryer as it’s listed."
The price is SAR 544
SAR 2,601 total
includes taxes & fees
6 May - 7 May
Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

Massive Roscoe Retreat: Great for Large Groups!

10.0 out of 10, Exceptional, (5)
"This house was as amazing in person as it was portrayed. Our friends and family had a wonderful time here. It was clean and spacious. The view was awesome and we got a front row seat for some snow fall. The house was just like the pictures. The Spa and sauna were an added bonus. We all had a wonderful time here."
Massive Roscoe Retreat: Great for Large Groups!

Amazing All-Season Private Lakefront Retreat!

10.0 out of 10, Exceptional, (52)
"I had the pleasure of staying at this beautiful lakeside cabin in the Catskills, and it was an unforgettable experience. From the moment we arrived, we were greeted by a home that was meticulously prepared and perfectly tidy. The cabin had an ample supply of fresh linens, towels, and toiletries, which made our stay comfortable and worry-free. The beds were incredibly comfortable, ensuring restful nights after days filled with outdoor activities. One of the highlights was the abundance of games...
Amazing All-Season Private Lakefront Retreat!

Amber Acres Lodge; Spacious Log Cabin with Mountain Views and Lake Access

10.0 out of 10, Exceptional, (18)
"We had the most amazing time and the place was perfect! Can’t wait to go back again. "
Amber Acres Lodge; Spacious Log Cabin with Mountain Views and Lake Access

Private Heated Pool• Hot Tub• Game Room• Fire Pit• 6 Bdrms

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great property. The amenities are perfect, and it has everything you might need! The hot tub, kitchen, indoor decor, perfect. Only note-there is a giant blue lives matter flag painted on the house, I did not see that in any photos. That might matter to some people either way, so wanted to bring it to your attention as a potential guest. "
The price is SAR 2,123
SAR 4,446 total
includes taxes & fees
7 May - 8 May
Private Heated Pool• Hot Tub• Game Room• Fire Pit• 6 Bdrms

Scenic Home on the Delaware River, Pet-Friendly!

9.8 out of 10, Exceptional, (6)
"Perfect stay for a trip to the ares for a family wedding."
Scenic Home on the Delaware River, Pet-Friendly!

5 minutes from original Woodstock site.

9.8 out of 10, Exceptional, (48)
"Our stay was awesome the space is beautiful and very clean easy to find!!!!"
The price is SAR 368
SAR 814 total
includes taxes & fees
19 May - 20 May
5 minutes from original Woodstock site.

1920’s charm. In-town retreat. Great for fly fishermen!! Pet Friendly

9.8 out of 10, Exceptional, (23)
"Great location for fishing excursions! Easy check in and clean house! Perfect accommodations for 2 fishermen."
1920’s charm. In-town retreat. Great for fly fishermen!! Pet Friendly

The Ipê House: Chic Catskills Cabin, 60min to Belleayre Mountain Ski

The Ipê House: Chic Catskills Cabin, 60min to Belleayre Mountain Ski

9-bedroom home with Private Indoor heated Pool - Firepit - 7 acres - sleeps 22

8.6 out of 10, Excellent, (4)
"Amazing stay at an amazing property. Great hosts. My families enjoyed it a lot."
9-bedroom home with Private Indoor heated Pool - Firepit - 7 acres - sleeps 22

Charming Catskills Lakefront Cottage

8.8 out of 10, Excellent, (10)
"The house was perfectly spacious and the outside area by the lake was amazing. Easy drive to the nearby small towns. Full of character and the house was well prepared."
Charming Catskills Lakefront Cottage
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

Postcard Cabins Western Catskills

2.0 star property
9.8 out of 10, Exceptional, (6)
"My Fiancé And Had Great Stay Here Very Peaceful & Clean. We Enjoyed Our Stay Here, It Was Great To Get Away From The City For A While"
The price is SAR 506
SAR 701 total
includes taxes & fees
20 May - 21 May
Postcard Cabins Western Catskills

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (151)
"Great cabin exactly as advertised. Go ahead and book it you won’t be disappointed. "
The price is SAR 465
SAR 1,244 total
includes taxes & fees
14 May - 15 May
Handcrafted Riverfront Cabin on 10 acres

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

9.0 out of 10, Wonderful, (73)
"We had an amazing stay at this property! Everything was exactly as described—clean, comfortable, and beautifully maintained. It felt like a true home away from home. The location was perfect, and all the amenities were thoughtfully provided.What really stood out was how smooth and stress-free the whole process was. Communication with the owner was excellent from start to finish—quick responses, clear instructions, and super helpful throughout. It made the entire experience even better.Highly...
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
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.