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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

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

Indoor Pool, 13 BR, Sleeps 34, 3 Luxury Homes
The pool at night, open 365 days of the year

Indoor Pool, 13 BR, Sleeps 34, 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 34, 3 Luxury Homes
A river runs through it
Miscellaneous

A river runs through it

10.0 out of 10, Exceptional, (4)
"This was our first time using VRBO, and also checking out the Catskills. It was perfect. The house is charming, unique, full of personality, and surrounded by breathtaking views. It snowed our entire trip and we had a roaring fire each night in the huge stone fireplace. It was perfectly relaxing and idyllic. The Sauna, darts, board games, and bar with vintage glasses were all highlights! We can’t wait to come back in the Spring or summer to see the river when it isn’t frozen. "
A river runs through it
Indoor Pool,11 Yrs Hosting, 7 bdrm, Hot Tub, Designer Home
Indoor/ outdoor pool partially open (surrounding pool fence not shown)

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

Indoor Pool,11 Yrs Hosting, 7 bdrm, Hot Tub, Designer Home
Completely renovated house in amenities-filled Masthope community / Ski Big Bear
Front of the house; driveway with plenty of parking space

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

10.0 out of 10, Exceptional, (7)
"Our stay was awesome. The house was so cozy and warm it felt like home. After a long day of snow boarding it was so nice to cozy up in bed to nice crisp clean smelling linens. We definitely recommend this house and will stay here again on our next trip. Thank you"
Completely renovated house in amenities-filled Masthope community / Ski Big Bear
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
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, (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!
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!
Charming & Private Delaware Riverfront Home near Callicoon NY
Exterior

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
Pool

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (28)
"Had 10 (50) friends get together for a long weekend in the mountains. The property is better than expected and the photos are accurate. Everyone had a bed which made this the right place. Great location and area for hiking. We were there in winter so unable to use the pool or pond, but that didn’t matter.Plenty of space for everyone. Multiple refrigerators, coffee machines and other great kitchen items for Cooking. The owners are great, easy to communicate with and very flexible / helpful,...
Breathtaking 44+ Acre Country Estate
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, (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
Property grounds

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

10.0 out of 10, Exceptional, (21)
"The property was nice, well maintained and clean. It worked perfectly for our group of 11. The kids loved all of the games in the basement. We had an issue with the hot water heater (breaker flipped) and the team was super responsive. "
Pocono Lackawaxen Masthope Lakefront Game Room Community Pool Ski Big Bear Kayak
Pocono Mountain Waterfront Escape in Masthope
Exterior detail

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 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
Poconos Home w/ Private Hot Tub & Fireplace
Pleasant Mount Vacation Rental | 2-Story Home | 4BR | 2.5BA | 1,875 Sq Ft

Poconos Home w/ Private Hot Tub & Fireplace

9.8 out of 10, Exceptional, (25)
"We were happy with our stay, the hot tub was a nice perk!"
Poconos Home w/ Private Hot Tub & Fireplace
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, (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
Exterior

Riverside Retreat in The Catskill Mountains

Riverside Retreat in The Catskill Mountains
Beaver Cottage · Beaver Cottage - Families - Groups

Beaver Cottage · Beaver Cottage - Families - Groups

10.0 out of 10, Exceptional, (4)
"Nice winter getaway. Great for a crowd. Cozy!"
The price is SAR 1,027
SAR 2,880 total
includes taxes & fees
23 Feb - 24 Feb
Beaver Cottage · Beaver Cottage - Families - Groups
Dancing Doe Estate with Wood Stove, Hot Tub & Firepit
Living Room with wood burning stove, flat screen tv and record player.

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
Cozy living room with ample seating for all

Sweet Village Waterfront Cottage w/ Nursery

The price is SAR 401
SAR 1,461 total
includes taxes & fees
18 Feb - 19 Feb
Sweet Village Waterfront Cottage w/ Nursery
Luxury Getaway in Jeffersonville, NY
Property grounds

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!
Exterior

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

9.0 out of 10, Wonderful, (69)
"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
Exterior

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (143)
"It was quite beautiful. The instructions left for us were easy to understand and we had no issues. "
The price is SAR 420
SAR 1,210 total
includes taxes & fees
25 Feb - 26 Feb
Handcrafted Riverfront Cabin on 10 acres
Postcard Cabins Western Catskills
Exterior

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 SAR 422
SAR 464 total
includes taxes & fees
6 Mar - 7 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.