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Compare 358 Vacation Homes in Callicoon with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (112)
"Beautiful home and property. Windows, skylights and wraparound deck were favorite features. Host Chris is friendly and thorough. "
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

Cozy Swan Lake Apt w/ Grill + Private Yard

9.6 out of 10, Exceptional, (14)
"Great private and quiet spot shared with many deer. Tastefully decorated and well equipped. Comfortable bed. Close to Bethel Woods via scenic back roads! "
Cozy Swan Lake Apt w/ Grill + Private Yard

Luxury Lakeside Paradise

9.6 out of 10, Exceptional, (4)
"Our family stayed for a number of days in Chaya's wonderful house on Swinging Bridges Lake. Everything about this house is great, and we would LOVE to come back! Thank you Chaya for being a gracious and attentive hostess!"
Luxury Lakeside Paradise

The Highland: a Cute Private Country Estate, Pool, GameRoom 18+ beds

2.0 star property
The Highland: a Cute Private Country Estate, Pool, GameRoom 18+ beds

Charming & Private Delaware Riverfront Home near Callicoon NY

9.8 out of 10, Exceptional, (171)
"Really a spectacular place to stay, beautiful and peaceful, comfortable and well-maintained. Hosts very responsive, even stopped by with a delicious apple pie and new cords for the internet! Would stay here again in a heartbeat. "
Charming & Private Delaware Riverfront Home near Callicoon NY

Pocono Lackawaxen Masthope Lakefront Game Room Community Pool Ski Big Bear Kayak

10.0 out of 10, Exceptional, (19)
"Location is great, house was beautiful. I recommend that place. "
Pocono Lackawaxen Masthope Lakefront Game Room Community Pool Ski Big Bear Kayak

Ski-in, Ski-out, beautifully renovated 4 bedroom, 4 bath, quiet cul-de-sac

10.0 out of 10, Exceptional, (34)
"Excellent property with modern ammenities. Nice fireplace with bluetooth speakers interconnected. Basement was perfect for kids for entertainment and privacy. Heated bathroom floor, front gas firepit and private deck with nice view. Not complaint about my stay. Only suggestions is the rental agreement should be part of the Vrbo process for more transperency and accountability. Overall, excellent property to retreat from fast paced life. "
Ski-in, Ski-out, beautifully renovated 4 bedroom, 4 bath, quiet cul-de-sac

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

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

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

9.6 out of 10, Exceptional, (26)
"We enjoyed our stay with a large gathering of friends and their families. The house was spacious and clean. We enjoyed the indoor swimming pool and sauna, as well the outdoor firepit and fishing in the pond. We also enjoyed the proximity to hiking and river rafting (which was kid-friendly). After the kids went to bed, the large dining area/ sun room provided a great space to socialize without having to worry about noise disturbing those who were sleeping. The only downside of the house was that...
Private Indoor Pool - Hot Tub - 2 Fishing Ponds - 33 Acres

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

9.6 out of 10, Exceptional, (38)
"The whole family had a great time! We would love to come back!"
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Pocono Cabin in Masthope Mountain Community

9.2 out of 10, Wonderful, (24)
"This is a neat little cozy spot near the Delaware Water Gap. My friends and I had a great time enjoying the quiet and the beautiful nature that surrounds the house. There is reliable wifi and decent cell service, and there were plenty of people around so we still felt safe. We were not accustomed to certain practices however, so be prepared. In order to access the lake, you need to have amenity badges, which was not clear to us until after we arrived (we booked understanding that amenity badges...
Pocono Cabin in Masthope Mountain Community

Beautiful Full-Size Private Lakefront Gated Home with dock / boats

9.8 out of 10, Exceptional, (134)
"Loved the house ,locations in view a wonderful stay, perfect sunset ,so quiet .This is the place when we want to come back and come back again."
Beautiful Full-Size Private Lakefront Gated Home with dock / boats

Waterfront Catskills Retreat on 2 Acres with Lots of Amenities, Close to Town

9.4 out of 10, Exceptional, (11)
"We are happy with the roomy home with space for everyone. Beautiful surroundings and easy to get to. "
Waterfront Catskills Retreat on 2 Acres with Lots of Amenities, Close to Town

Sun Drenched Lakefront Cove

9.2 out of 10, Wonderful, (15)
"We had a great time! Plenty of room and very clean."
Sun Drenched Lakefront Cove

Beautiful cabin in the woods

9.6 out of 10, Exceptional, (10)
"The property is great. The owner was always in communication with me. A great stay."
Beautiful cabin in the woods

On the Delaware River, beautiful views, fishing, kayaking, floating, swimming

10.0 out of 10, Exceptional, (6)
"The house was perfect, it had everything we needed. The beds and bedding were very comfortable. The view was gorgeous and relaxing. The fishing was great. Dawn is a wonderful host and Jordan was extremely helpful during our stay. We will definitely be back. "
On the Delaware River, beautiful views, fishing, kayaking, floating, swimming

LARGE RUSTIC BRICK SCHOOL HOUSE WITH MUSIC JAMSPACE /RECORDING STUDIO

9.6 out of 10, Exceptional, (47)
"Lovely space with lots of character and a great place for enjoying music, loved how each room had a CD collection and speakers. "
LARGE RUSTIC BRICK SCHOOL HOUSE WITH MUSIC JAMSPACE /RECORDING STUDIO

Amazing Lakefront! Weekly/Monthly Discounts! ☀️

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 Lakefront! Weekly/Monthly Discounts! ☀️

Riverfront Luxe in Narrowsburg

10.0 out of 10, Exceptional, (13)
"Just as described! Can't wait to come back."
The price is AED 694
AED 2,071 total
includes taxes & fees
8 Jan - 9 January 2025
Riverfront Luxe in Narrowsburg

Pet-Friendly Hancock Home on the Delaware River!

9.8 out of 10, Exceptional, (19)
"Couldnt ask for a better location or a house better situated to enjoy it. Watching eagles, deer, ducks, fishermen and we think a bear. We are 3 eomen in town for a high school reunion, could have used a second bath."
Pet-Friendly Hancock Home on the Delaware River!
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

Callicoon Creek House with Pool + Hot Tub

8.0 out of 10, Very Good, (1)
"It's a charming house in a great location. Friendly and responsive host, and you will have everything you need. Great lawn for the dog as well. "
Callicoon Creek House with Pool + Hot Tub

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (137)
"This cabin was very charming, clean and a great spot to getaway from the everyday grind. The cabin was the perfect size for me, my husband and our dog. Everything we needed was at the cabin and our host was accommodating. We will be back in the future "
The price is AED 411
AED 1,197 total
includes taxes & fees
13 Jan - 14 January 2025
Handcrafted Riverfront Cabin on 10 acres

Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

10.0 out of 10, Exceptional, (173)
"Great Inside/Outside"
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
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.