Photo by Matthew Jay

Callicoon Holiday Rentals

  • 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

This weekend
Next weekend

Holiday Rentals in Callicoon

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (140)
"Property was clean and just the right size for our group of 2 people and 2 dogs. Had a great time disconnecting from our everyday and walking the property. Hosts were responsive and helpful. "
The price is AU$510
includes taxes & fees
10 Feb - 11 Feb
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 AU$219
includes taxes & fees
10 Feb - 11 Feb
Postcard Cabins Western Catskills

Experience Delaware Riverfront cabin nestled in the woods, Pet/Family Friendly

9.6 out of 10, Exceptional, (206)
"Great experience"
Experience Delaware Riverfront cabin nestled in the woods, Pet/Family Friendly

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

10.0 out of 10, Exceptional, (177)
"Great experience, the hosts were amazing. It was such a nice serene getaway for us. "
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

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

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

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

Lakefront Cottage - Dog Friendly

9.8 out of 10, Exceptional, (16)
"The place was amazing. It was a little difficult to find at first. I didnt see any address numbers on the outside of the cottage. The view was amazing, the actual cottage was stunning, clean, and looked even better in person than in the photos."
Lakefront Cottage - Dog Friendly

Brand New! Riverfront River Bend Cabin - Catskill fly fishing outside your door!

10.0 out of 10, Exceptional, (22)
"Unfortunately due to an unexpected illness after attending an unexpected wake, my wife and I could not make it to the cabin. As we both appreciate the weekend adjustment, we wanted to thank Rachel and John for their help. We hope to rent the cabin in the near future for a well needed time away. Happy New Year. "
Brand New! Riverfront River Bend Cabin - Catskill fly fishing outside your door!

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

9.8 out of 10, Exceptional, (37)
"Hilltop Farmhouse was an amazing experience with plenty of room for all! Lots of different activities in the house to enjoy! Highly recommend staying here 10/10 will definitely be back"
This house is a 7 bedrooms, 4 bathrooms, located in Beach Lake, PA.

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

8.0 out of 10, Very good, (2)
"This house was perfect for our family getaway. There are 13 of us. Finding a house that offers not only enough bedrooms but also a large enough table for our family meals is always challenging. This house fit the bill. The pool was an awesome plus for a winter getaway. The kitchen was fully stocked with everything we needed.EEveryone "
9-bedroom home with Private Indoor heated Pool - Firepit - 7 acres - sleeps 22

Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

9.6 out of 10, Exceptional, (106)
"My husband and I stayed for our anniversary week in early September and the place could not have been more perfect! The photos in the listening don't do the property justice. The lake was spectacular. Perfect location with rustic cabin charm!"
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

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!

Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski

9.6 out of 10, Exceptional, (20)
"Our stay was great! Host was great at communicating. Enough towels were supplied. Beds were very comfortable. Highly recommended!"
Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski

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

Cozy lake front unit close to Honesdale, Elk Mountain, Scranton & much more!

9.8 out of 10, Exceptional, (105)
"Place was cute. Very clean and has everything you need. Location is nice. Lake is walking distance. Very pretty. Kept losing power all night and morning. Then it snowed so we had to leave a day early to avoid getting stuck. Drove 3 hrs and only stayed 16 hrs total. Not a good trip. It would have been nice if we got a partial credit. Pete and Maida"
Cozy lake front unit close to Honesdale, Elk Mountain, Scranton & much more!

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

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, (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

DeerRidge Estate By Brophy

10.0 out of 10, Exceptional, (49)
"We are a group of college friends who have been getting together for over forty years. We’ve stayed at a variety of places over the years and now, with 3 generations attending, we need larger accommodations. I think we’ve found our place. Lovely setting. Clean, comfortable rooms. Plenty of bathrooms! We had perfect weather but even if there were rain, the front veranda offers lots of space to hang out. (A few rocking chairs would be nice for the babies and grandparents.) Overall, a lovely...
DeerRidge Estate By Brophy

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

9.6 out of 10, Exceptional, (27)
"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
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 types of properties in Callicoon you may be interested in

Villa Roma Resort and Conference Center

3.0 star property
6.6 out of 10, (329)
"Something special to do after holiday season"
The price is AU$385
includes taxes & fees
10 Feb - 11 Feb
Villa Roma Resort and Conference Center

The Kartrite Resort & Indoor Waterpark

4.0 star property
8.0 out of 10, Very good, (1227)
"Great place"
The price is AU$474
includes taxes & fees
9 Feb - 10 Feb
The Kartrite Resort & Indoor Waterpark

Resorts World Catskills Casino

4.5 star property
8.8 out of 10, Excellent, (1001)
"-"
The price is AU$341
includes taxes & fees
10 Feb - 11 Feb
Resorts World Catskills Casino
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.

Frequently asked questions

Are there holiday rentals in Callicoon?

Yes, there are holiday rentals close to the most popular sights in Callicoon, or you can select a more secluded option if you're looking for a relaxing stay. Callicoon is known for its entertainment choices and gardens.

What are some of the best holiday rentals that Callicoon has to offer?

Indoor Pool, 13 BR, Sleeps 39, 3 Luxury Homes : This holiday home rental outside of Callicoon is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 13 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Callicoon?

With 16 Expedia holiday rentals, you're guaranteed to find just the right place for your Callicoon stay.

What’s there to see and do in Callicoon?

Upper Delaware Scenic and Recreational Area and Upper Delaware River are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Big Island and Villa Roma Driving Range.

What’s a holiday rental in Callicoon like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Callicoon. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.