Photo by Matthew Jay

Callicoon Holiday Rentals

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Holiday Rentals in Callicoon

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

10.0 out of 10, Exceptional, (132)
"Stay was great trash in the back was still there since last people but other than that was Great"
The price is AU$535
includes taxes & fees
3 Dec - 4 Dec
Handcrafted Riverfront Cabin on 10 acres

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

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

Riverfront Cabin nestled between the Poconos/Catskills, Pet/Family Friendly

9.6 out of 10, Exceptional, (203)
"The cabin was a great getaway. I love that they supplied fire wood for the fireplace. It's definitely off the beaten path with a great view. We would definitely stay there again. "
Riverfront Cabin nestled between the Poconos/Catskills, Pet/Family Friendly

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!

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

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.

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.

Mountain Retreat- Masthope-Ski/Lake Community!

10.0 out of 10, Exceptional, (12)
"Great area, super friendly and helpful owners. made the stay super easy. close to alot of amenities. house was great, games in basement made the nights in a blast."
Mountain Retreat- Masthope-Ski/Lake Community!

EV Modern Cozy Waterfront Cottage with Fireplace

10.0 out of 10, Exceptional, (21)
"We were surprised when we first arrived, but were very pleasantly surprised when we got inside. The place was very clean and nice. Jonathan was very prompt with the few questions we had."
EV Modern Cozy Waterfront Cottage with Fireplace

Mountaintop Property on 8 acres

8.2 out of 10, Very good, (79)
"Pros: cozy, quiet and secluded property, near Main Street with good options for food and shopping, comfortable bed, Morgan was super responsive. Cons: As a number of other reviewers started (and found to be surprising) the A frame unit is just one of 2 rentals which are connected and share many thin walls — we were shocked to find out we were not alone. We were only told about them once we heard their footsteps and inquired with Morgan. Kitchen needs some love and care, no frills but can...
The price is AU$305
includes taxes & fees
25 Nov - 26 Nov
Mountaintop Property on 8 acres

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

Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!

10.0 out of 10, Exceptional, (23)
"We loved our stay at this beautiful home! The property was nicely situated in a wooded neighborhood and the inside was very clean. We will definitely be returning. Also highly recommend a walk around the nearby lake and a visit to some local breweries! "
The price is AU$603
includes taxes & fees
23 Dec - 24 Dec
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!

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

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

Cozy Big Bear Mountain Ranch at Masthope

9.4 out of 10, Exceptional, (14)
"This house and neighborhood were exactly what we needed - peace, quiet, and solitude away from the busyness of our area. Hiking each day, reading a good book on the couch and backyard, fires in the chiminea each evening and night. The weekend exceeded our expectations. We will be back! "
Cozy Big Bear Mountain Ranch at Masthope

Chic Treehouse Cabin with Hot Tub, SUPs, BBQ, Fire Pit, Lake Access, Pedal Boat

9.2 out of 10, Wonderful, (11)
"Very cute bungalow. Clean. Quiet. Enjoyed ourselves very much!"
Chic Treehouse Cabin with Hot Tub, SUPs, BBQ, Fire Pit, Lake Access, Pedal Boat

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

10.0 out of 10, Exceptional, (171)
"A quiet peaceful property with horses goats and ducks to meet! Heating was great in the cabin. We enjoyed sitting on the front porch getting some fresh air."
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
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 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, (326)
"We stayed overnight following a concert at Bethal Woods. Morning coffee station would have been nice, we had to wait unti the dining room opened at 7:30am but a good overall experience. "
The price is AU$348
includes taxes & fees
5 Dec - 6 Dec
Villa Roma Resort and Conference Center

The Kartrite Resort & Indoor Waterpark

4.0 star property
7.8 out of 10, Good, (1090)
"Other than the one restaurant, food was pretty awful- and TJ e Waterpark was relatively small, but was clean and the room/arcade/jump pad, etc were nice"
The price is AU$497
includes taxes & fees
1 Dec - 2 Dec
The Kartrite Resort & Indoor Waterpark

Resorts World Catskills Casino

4.5 star property
8.8 out of 10, Excellent, (1002)
"Lisette at front desk, Darius the bellman and Tamica from housekeeping were all very helpful and supportive to make our stay very good. This was the third two night stay for my wife and I in just over two months We plan to visit again in December or January, maybe both We had the same room on the 18th floor corner each time It gave us time to unwind and enjoy the casino We take a leisurely 4 hour drive from Bucks county PA and are happy we found this property"
The price is AU$314
includes taxes & fees
1 Dec - 2 Dec
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.
Beautiful view of the beach with palm trees

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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 + 3 Homes + Private Lodge/ Entertainment Clubhouse: 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 24 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. In the wider area, you’ll find Big Island and Bethel Woods.

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.