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Compare 346 Vacation Homes in Callicoon with updated reviews, rates, and availability.

Indoor Pool, 13 BR, Sleeps 39, 3 Luxury Homes

10.0 out of 10, Exceptional, (44)
"We have a group of 25 that have been celebrating New Year’s together for the past 30 years. This worked great as everyone had their own bedroom and there was plenty to do on-site. The clubhouse and pool were enjoyed by all! We look forward to staying there again next year."
Indoor Pool, 13 BR, Sleeps 39, 3 Luxury Homes

A river runs through it

10.0 out of 10, Exceptional, (6)
"If you want to be amazed at the interior design, stunning fireplace and decor; this is the place for you. Get your heart pumping walking up the steps to the entrance; before going indoors look at the beautiful mountain surround!"
A river runs through it

Indoor Pool,11 Yrs Hosting, 7 bdrm, Hot Tub, Designer Home

10.0 out of 10, Exceptional, (1)
"Great stay all around "
Indoor Pool,11 Yrs Hosting, 7 bdrm, Hot Tub, Designer Home

Completely renovated house in amenities-filled Masthope community / Ski Big Bear

10.0 out of 10, Exceptional, (8)
"Very clean, all renovated and streamlined. The property owners are delightful, easy to work with, and responsive. Great community, the skiing was lovely, and we would definitely do it again."
Completely renovated house in amenities-filled Masthope community / Ski Big Bear

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

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

This house is a 7 bedrooms, 4 bathrooms, located in Beach Lake, PA.

9.8 out of 10, Exceptional, (38)
"The house was very fun! We had room for 14 of us. The older kids liked that there was a tv in each bedroom. The pool was the perfect temperature and we all had a great time swimming. The kitchen had plenty of dishes and pots for everything we needed."
This house is a 7 bedrooms, 4 bathrooms, located in Beach Lake, PA.

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

9.6 out of 10, Exceptional, (39)
"A wonderful host with a beautiful & comfortable home. All the necessities, plus more! A must stay at. "
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

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

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (29)
"We really enjoyed the seclusion of the property, it truly felt like a getaway. The house was very clean upon arrival and the kitchen was the perfect size for our group. Overall we had a great stay. The only critique I would have is that I did not realize that the only way to access one of the rooms was to walk through another. Perhaps I did not read the listing thoroughly but I was unaware of that condition."
Breathtaking 44+ Acre Country Estate

House w/ Hot Tub on 10 Acres near Delaware River

10.0 out of 10, Exceptional, (18)
"It is a great house with everything well-equipped. Although the structure is small, it is convenient and well-equipped. I am glad that I was able to enjoy a pleasant vacation. Thank you."
House w/ Hot Tub on 10 Acres near Delaware River

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

10.0 out of 10, Exceptional, (22)
"Great home, suits all of our families needs! This was our 4th year and we plan on returning ! "
Pocono Lackawaxen Masthope Lakefront Game Room Community Pool Ski Big Bear Kayak

Pocono Mountain Waterfront Escape in Masthope

2.0 star property
10.0 out of 10, Exceptional, (5)
"Our group had a blast staying at this lovely house. We should have extended the stay longer. The kids had fun kayaking, pedaling, and rowing the boat which were provided by the home owner. The adults enjoyed the hot tub overlooking the gorgeous lake. The interior of the house is very modern and cozy. When opportunity arise, I’ll like to book another weekend getaway there. I’ll like to thank the host again for their hospitable services. "
Pocono Mountain Waterfront Escape in Masthope

LARGE BRICK SCHOOL HOUSE NEAR NY/PA UPPER DELAWARE RIVER WITH MUSIC 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 BRICK SCHOOL HOUSE NEAR NY/PA UPPER DELAWARE RIVER WITH MUSIC STUDIO

Private Hot Tub & Fireplace: Poconos Home!

9.8 out of 10, Exceptional, (25)
"We loved the space, everything was there to make an amazing experience. The kids from Florida saw snow for the first time. Learned to ski at elk and used a sled we brought along on a small hill at the home. Thank you for a wonderful stay! "
Private Hot Tub & Fireplace: Poconos Home!

Spacious Home w/ Deck, Grill & Delaware River View

9.2 out of 10, Wonderful, (43)
"Comfortable, clean and well appointed. Beautiful views of the river, we enjoyed our stay!"
Spacious Home w/ Deck, Grill & Delaware River View

Riverside Retreat in The Catskill Mountains

Riverside Retreat in The Catskill Mountains

Beaver Cottage · Beaver Cottage - Families - Groups

10.0 out of 10, Exceptional, (4)
"Nice winter getaway. Great for a crowd. Cozy!"
The price is AED 804
AED 2,581 total
includes taxes & fees
9 Mar - 10 Mar
Beaver Cottage · Beaver Cottage - Families - Groups

Dancing Doe Estate with Wood Stove, Hot Tub & Firepit

4.0 star property
10.0 out of 10, Exceptional, (2)
"We really enjoyed a post-holiday getaway in the cozy Dancing Doe Estate. It was the perfect house to relax, unwind and welcome in my husband's 50th trip around the sun. "
Dancing Doe Estate with Wood Stove, Hot Tub & Firepit

Sweet Village Waterfront Cottage w/ Nursery

The price is AED 393
AED 1,449 total
includes taxes & fees
5 Mar - 6 Mar
Sweet Village Waterfront Cottage w/ Nursery

Luxury Getaway in Jeffersonville, NY

Luxury Getaway in Jeffersonville, NY
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)
"Cozy cabin with warm vibe and good supplemental wood stove in winter snow storm for 5 days. Blazing snow trails with dog around lovely property and over to the river. Host superbly responsive. Will be back in fishing season as this is on the Delaware."
The price is AED 422
AED 1,197 total
includes taxes & fees
5 Mar - 6 Mar
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 454 total
includes taxes & fees
25 Mar - 26 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.