Photo by Matthew Jay

Search Vacation Homes in Callicoon

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 411 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, (71)
"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!

In the cloud ~your cozy lake house

9.6 out of 10, Exceptional, (85)
"Great spot."
The price is SAR 694
SAR 1,203 total
includes taxes & fees
23 Mar - 24 Mar
In the cloud ~your cozy lake house

8 Mi to Lake Wallenpapack: Gem w/ Deck & Game Room

6.0 out of 10, (2)
"We booked this property to celebrate my boyfriend's 30th birthday, as we were going on a ski/snowboarding trip to Elk Mountain. The game room was a key reason for choosing this rental, but we couldn't use it at all due to severe heating issues. The wall & floor heating units did not work in the game room or the downstairs bedrooms, leaving everyone who slept downstairs freezing. The game room was so cold that no one could stay in there for more than a minute. When we contacted the host, they...
8 Mi to Lake Wallenpapack: Gem w/ Deck & Game Room

Sun Drenched Lakefront Cove

9.2 out of 10, Wonderful, (16)
"We had a great time! Plenty of room and very clean."
Sun Drenched Lakefront Cove

Charming & Private Delaware Riverfront Home near Callicoon NY

9.8 out of 10, Exceptional, (172)
"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

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

10.0 out of 10, Exceptional, (116)
"My friends and I stayed at this perfect woodsy retreat for my 28th birthday and had so much fun. The kitchen is perfect for cooking big meals and everything you need is available. It was cozy and warm for our winter stay, but I look forward to booking again in the spring and summer. Chris is an excellent host and was very communicative! "
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

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

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

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

9.6 out of 10, Exceptional, (27)
"The house was stocked with all the essentials, the owner was very responsive and the overall experience was fantastic. Would recommend for a large group - more than enough space! "
Private Indoor Pool - Hot Tub - 2 Fishing Ponds - 33 Acres

Lake Front Heated Floors Romantic Hot Tub Firepit Foosball Ski Screen Porch Boat

9.4 out of 10, Exceptional, (54)
"Awesome. So peaceful relaxing, feel rejuvenated having stayed there. Thanks Scott"
Lake Front Heated Floors Romantic Hot Tub Firepit Foosball Ski Screen Porch Boat

ELK Mountain• Hot Tub• Game Room• Fire Pit• 6 Bdrms

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!"
ELK Mountain• Hot Tub• Game Room• Fire Pit• 6 Bdrms

Starlight Lakehouse; Your Magical 5 Bdrm Getaway! W/ BRAND NEW 7 SEATER HOT TUB!

8.4 out of 10, Very Good, (9)
"Great house right on the water. Beautiful view of the lake. Many bedrooms that comfortably fit 7 adults and 1 child. The host is great, and very communicative in case you need anything. Highly recommend!!"
Starlight Lakehouse; Your Magical 5 Bdrm Getaway! W/ BRAND NEW 7 SEATER HOT TUB!

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!!!!"
5 minutes from original Woodstock site.

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, (39)
"We had so much fun and everyone was so accommodating and kind!"
This house is a 7 bedrooms, 4 bathrooms, located in Beach Lake, PA.

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

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

8.0 out of 10, Very Good, (3)
"It was amazing. the house is more than equipped for bigger families/ groups. There were 19 of us, 11 were kids. Plenty of stuff to do, rooms were spacious and comfortable. Pool was AMAZING and cannot say enough about the HOST. He answered every questions and was so accommodating. We will definitely be back!! "
9-bedroom home with Private Indoor heated Pool - Firepit - 7 acres - sleeps 22

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

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
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.
Don't see what you're looking for?
See all available properties in Callicoon
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Callicoon

Postcard Cabins Western Catskills

2.0 star property
9.4 out of 10, Exceptional, (3)
"The tiny cabin was so cute. Unfortunately it rained the day before we got there so everything was muddy including the outside of our cabin. It made enjoying the outside difficult. Overall it was lovely and looking forward to going back. "
The price is SAR 422
SAR 464 total
includes taxes & fees
7 Apr - 8 Apr
Postcard Cabins Western Catskills

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

9.0 out of 10, Wonderful, (71)
"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, (147)
"Log cabin and property exceeded our expectationsWe plan to return in the fall to see the leaves change"
The price is SAR 581
SAR 1,402 total
includes taxes & fees
26 Mar - 27 Mar
Handcrafted Riverfront Cabin on 10 acres
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.