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Search Vacation Homes in Callicoon

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Compare 341 Vacation Homes in Callicoon with updated reviews, rates, and availability.

Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
Enjoy the privacy of the Cochecton woods around you.

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

10.0 out of 10, Exceptional, (111)
"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
Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse
Here's the pool with the cover retracted and the segments stacked together.

Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse

10.0 out of 10, Exceptional, (43)
"We had an absolute BLAST at this house!!!! Honestly, the pictures did not do it justice. The beautiful views around, waking up to morning fog, the amount of sprawling space across all 4 properties. I can’t say enough great things. It was so clean and had everything we needed. We WILL be back!"
Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse
Cozy Swan Lake Apt w/ Grill + Private Yard
Swan Lake Vacation Rental | 1BR | 1BA | 700 Sq Ft | Stairs Required to Enter

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

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

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

9-bedroom home with Private Indoor heated Pool - Firepit - 7 acres - sleeps 22
Spacious Home w/ Deck, Grill & Delaware River View
Callicoon Vacation Rental | 2BR | 1BA | 1,536 Sq Ft | Stairs Required

Spacious Home w/ Deck, Grill & Delaware River View

9.2 out of 10, Wonderful, (42)
"Enjoyed the private river view and wild life that visited everyday. Everything was as advertised. "
Spacious Home w/ Deck, Grill & Delaware River View
Pet-Friendly Hancock Home on the Delaware River!
Hancock Vacation Rental | 2BR | 1BA | 2 Steps Required | 1,200 Sq Ft

Pet-Friendly Hancock Home on the Delaware River!

9.8 out of 10, Exceptional, (18)
"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!
House w/ Hot Tub on 10 Acres near Delaware River
Living area

House w/ Hot Tub on 10 Acres near Delaware River

10.0 out of 10, Exceptional, (16)
"Property is great and the cabin feels truly lived in and comfortable. Hot tub and fire pit were highlights. Bring your own charcoal for grill and firewood for various fireplaces"
House w/ Hot Tub on 10 Acres near Delaware River
The Ipê House: Chic Catskills Cabin, 60min to Belleayre Mountain Ski
Living area

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

The Ipê House: Chic Catskills Cabin, 60min to Belleayre Mountain Ski
Recently renovated house in Hancock, NY near Delaware River
Exterior

Recently renovated house in Hancock, NY near Delaware River

10.0 out of 10, Exceptional, (9)
"Stayed before, and hope to stay again. Thank you. "
Recently renovated house in Hancock, NY near Delaware River
Lux Home/Serene Pond/Pool/Hot Tub/Game Room
Property grounds

Lux Home/Serene Pond/Pool/Hot Tub/Game Room

2.0 star property
10.0 out of 10, Exceptional, (2)
"Our stay was perfect! This house was absolutely beautiful and spacious. Perfect for large groups. It had everything we needed and then some. Highly recommend staying here!"
Lux Home/Serene Pond/Pool/Hot Tub/Game Room
A river runs through it
Miscellaneous

A river runs through it

10.0 out of 10, Exceptional, (1)
"Our family of 4 thoroughly enjoyed our stay. We loved the artsy and funky decor. The location and grounds are picturesque. You can easily spend all day at the house birdwatching, fishing, roasting marshmallows at the fire pit, or enjoying the sauna. There are also many nearby towns and hikes to eplore. We plan on staying again. "
A river runs through it
Private Indoor Pool - Hot Tub - 2 Fishing Ponds - 33 Acres
Pool

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!
Exterior

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!
Beautiful Full-Size Private Lakefront Gated Home with dock / boats
View from upper deck

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
This house is a 7 bedrooms, 4 bathrooms, located in Beach Lake, PA.
Indoor Pool and lots of seating. The pool is heated thru the Winter.

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

9.8 out of 10, Exceptional, (32)
"Perfect spot for 3 families with kids. Hope to be back next year!"
This house is a 7 bedrooms, 4 bathrooms, located in Beach Lake, PA.
Breathtaking 44+ Acre Country Estate
Pool

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (25)
"Jennifer was a great host, very communicative. The property is really beautiful and the sunsets/sunrises were wonderful to watch from the porch and the fire pit! The pictures from the listing were accurate. Overall a great stay"
Breathtaking 44+ Acre Country Estate
Pocono Lackawaxen Masthope Lakefront Game Room Community Pool Ski Big Bear Kayak
Property grounds

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

10.0 out of 10, Exceptional, (18)
"Location is great, house was beautiful. I recommend that place. "
Pocono Lackawaxen Masthope Lakefront Game Room Community Pool Ski Big Bear Kayak
Beautiful cabin in the woods
This view is the living room, as seen from the first seat at the dining table.

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
LARGE RUSTIC BRICK SCHOOL HOUSE WITH MUSIC JAMSPACE /RECORDING STUDIO
Exterior

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
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
Exterior

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
Exterior

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (132)
"We were looking for something that was NOT a city. This place was perfect. The area the cabin. A log cabin like the ones you see in movies. We will be back looking forward to seeing it in the other seasons. The owners was super communicative and easy to get a hold of."
The price is AED 459
AED 1,249 total
includes taxes & fees
27 Nov - 28 Nov
Handcrafted Riverfront Cabin on 10 acres
Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse
Here's the pool with the cover retracted and the segments stacked together.

Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse

10.0 out of 10, Exceptional, (43)
"We had an absolute BLAST at this house!!!! Honestly, the pictures did not do it justice. The beautiful views around, waking up to morning fog, the amount of sprawling space across all 4 properties. I can’t say enough great things. It was so clean and had everything we needed. We WILL be back!"
Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse
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.