A rural landscape with a house surrounded by autumn-colored trees and rolling hills.

Callicoon Holiday Rentals

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Our top choices for Callicoon holiday rentals

1. Bright Modern Home * Wood-Stove Nights * Big Deck

Bright Modern Home * Wood-Stove Nights * Big Deck
Callicoon
10.0 out of 10, Exceptional, (2 reviews)
"Perfect for a quiet get away. And the beds were very comfy and the sheets very nice quality, we slept so well!"
United States
Anonymous traveller
The price is NZ$983
includes taxes & fees
2 Nov - 3 Nov
Bright Modern Home * Wood-Stove Nights * Big Deck

2. Callicoon Creek Farmhouse

Callicoon Creek Farmhouse
Callicoon
9.4 out of 10, Exceptional, (12 reviews)
"In town for a family gathering. House was perfect for our needs. Will recommend"
United States
Tom B.
The price is NZ$605
includes taxes & fees
27 Oct - 28 Oct
Callicoon Creek Farmhouse

3. Postcard Cabins Western Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Western Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Roscoe
9.4 out of 10, Exceptional, (203 reviews)
"Place was very quiet and it has a beautiful view"
United States
Leandro
The price is NZ$310
includes taxes & fees
9 Nov - 10 Nov
Postcard Cabins Western Catskills, Outdoor Collection by Marriott Bonvoy

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

Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
Narrowsburg
10.0 out of 10, Exceptional, (165 reviews)
"Such a beautiful place to stay and explore with my pup!"
United States
Alison H.
The price is NZ$541
includes taxes & fees
15 Oct - 16 Oct
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

5. Lakeview Cabin Duplex

Lakeview Cabin Duplex
Lake Huntington
9.6 out of 10, Exceptional, (25 reviews)
"Great stay!"
United States
melissa m.
The price is NZ$407
includes taxes & fees
10 Nov - 11 Nov
Lakeview Cabin Duplex

6. Property of Big Foot Roscoe, NY

Property of Big Foot Roscoe, NY
Roscoe
9.8 out of 10, Exceptional, (10 reviews)
"Quiet place with fantastic hosts!"
United States
Jeremy H.
The price is NZ$243
includes taxes & fees
13 Oct - 14 Oct
Property of Big Foot Roscoe, NY

7. Glamping in Vintage Airstream with modern comforts with private pond access.

Glamping in Vintage Airstream with modern comforts with private pond access.
Cochecton
9.8 out of 10, Exceptional, (21 reviews)
"Second time staying here for a concert, so easy!!"
United States
Carrie W.
The price is NZ$617
includes taxes & fees
20 Oct - 21 Oct
Glamping in Vintage Airstream with modern comforts with private pond access.

8. Victorian Lake Oasis | Hot Tub | Private Lakefront

Victorian Lake Oasis | Hot Tub | Private Lakefront
Damascus
9.8 out of 10, Exceptional, (10 reviews)
"I was working in the area with two other coworkers and this house was perfect. It had everything we needed and was walking distance to great restaurants. I would definitely stay again if in the area. "
United States
Dave
The price is NZ$762
includes taxes & fees
14 Oct - 15 Oct
Victorian Lake Oasis | Hot Tub | Private Lakefront

9. Cozy 2-bedroom cabin in serene Lake Huntington with AC

Cozy 2-bedroom cabin in serene Lake Huntington with AC
Lake Huntington
10.0 out of 10, Exceptional, (1 review)
"Clean newly renovated cabins where you wake to a beautiful view of the lake and access to boats for the lake. Big deck. Really comfortable."
United States
S C.
The price is NZ$449
includes taxes & fees
19 Oct - 20 Oct
Cozy 2-bedroom cabin in serene Lake Huntington with AC

10. Charming 1 bedroom apartment with AC in quaint Roscoe

Charming 1 bedroom apartment with AC in quaint Roscoe
Roscoe
7.0 out of 10, Good, (2 reviews)
"Nice venue and owner is very nice and lives in the house that is attached. He needs to make some adjustments. We hope this is helpful to him. Most important, he absolutely needs to dump the mattress that is on the bed. It is not supportive. It's way too soft and I woke up each morning with a very hurting back. Other things: need to get a non slip mat for the shower. Needs to leave written instructions with the wifi code. Needs to add tissue boxes. Needs to add an extension cord so that you can...
United States
Lawrence
The price is NZ$216
includes taxes & fees
12 Oct - 13 Oct
Charming 1 bedroom apartment with AC in quaint Roscoe

11. In the cloud ~your cozy lake house

In the cloud ~your cozy lake house
Swan Lake
9.6 out of 10, Exceptional, (119 reviews)
"We had a wonderful one night stay!"
United States
Anonymous traveller
The price is NZ$613
includes taxes & fees
21 Oct - 22 Oct
In the cloud ~your cozy lake house

12. Cozy Farm Private Artistic Eclectic Cabin - 183 beautiful acres

Cozy Farm Private Artistic Eclectic Cabin - 183 beautiful acres
Callicoon Center
10.0 out of 10, Exceptional, (29 reviews)
"Dr. Norris is the best host ever. The house is beautiful. The amenities amazing. A walk around the property is a must. "
United States
Miguel A.
Cozy Farm Private Artistic Eclectic Cabin - 183 beautiful acres

13. Cozy Camper at Roscoe Wildlife Retreat

Cozy Camper at Roscoe Wildlife Retreat
Roscoe
9.6 out of 10, Exceptional, (9 reviews)
"Great place to stay. Very clean. Owners were friendly and accommodating. There's chickens roaming, I bet they'd give you a couple eggs if you ask. Super nice people. I would definitely stay again"
United States
James
The price is NZ$323
includes taxes & fees
18 Oct - 19 Oct
Cozy Camper at Roscoe Wildlife Retreat

14. Roscoe Coop Clucking Crazy Hut

Roscoe Coop Clucking Crazy Hut
Roscoe
10.0 out of 10, Exceptional, (10 reviews)
"Mike & Debbie are wonderful hosts, very social but don't push past what you're comfortable with. There little camp is neat, clean, beautiful set up. They provide towels, shampoo & body wash! My kind of camping. There is a bit of a hill to get to the cabins but they also have an accessible cottage for someone may need it. Their 2 pups, Luna & Roxy, will great you & check on you throughout the day. You'll love your stay!"
United States
Marybeth
The price is NZ$235
includes taxes & fees
13 Oct - 14 Oct
Roscoe Coop Clucking Crazy Hut

15. Woods I GO 2 Lose my Mind Roscoe

Woods I GO 2 Lose my Mind Roscoe
Roscoe
10.0 out of 10, Exceptional, (6 reviews)
"Hosts are super friendly and helpful. Property was clean and peaceful. Highly recommend!"
United States
Ashley B.
The price is NZ$290
includes taxes & fees
19 Oct - 20 Oct
Woods I GO 2 Lose my Mind Roscoe

16. Mountaintop Property on 8 acres

Mountaintop Property on 8 acres
Honesdale
8.2 out of 10, Very good, (99 reviews)
"Beautiful property and surrounding area, host is very friendly"
United States
Liam N.
The price is NZ$300
includes taxes & fees
4 Nov - 5 Nov
Mountaintop Property on 8 acres

17. Mountaintop Hideaway ~ Piece of Paradise - Apt

Mountaintop Hideaway ~ Piece of Paradise - Apt
Honesdale
9.0 out of 10, Wonderful, (30 reviews)
"It was a nice"
United States
Olympia B.
The price is NZ$368
includes taxes & fees
12 Oct - 13 Oct
Mountaintop Hideaway ~ Piece of Paradise - Apt

18. Roscoe Cottage Pet Friendly

Roscoe Cottage Pet Friendly
Roscoe
9.8 out of 10, Exceptional, (20 reviews)
"The cottage is very adorable and a great place if your looking to get away from the city life"
United States
Darwin
The price is NZ$448
includes taxes & fees
13 Oct - 14 Oct
Roscoe Cottage Pet Friendly

19. Coop 002

Coop 002
Kenoza Lake
The price is NZ$779
includes taxes & fees
1 Nov - 2 Nov
Coop 002

20. Roscoe RV Pet Friendly

Roscoe RV Pet Friendly
Roscoe
9.8 out of 10, Exceptional, (9 reviews)
"Debra was a wonderful host who went above and beyond to ensure we had a cozy and comfortable stay! Highly recommend staying at this property and will definitely be back!"
United States
Dawn H.
The price is NZ$411
includes taxes & fees
20 Oct - 21 Oct
Roscoe RV Pet Friendly
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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Top Callicoon Hotel Reviews

Find out more about Callicoon

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Callicoon holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Callicoon. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Callicoon. Seeing all the best attractions is bound to make you fall in love with Callicoon. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Callicoon short-term rentals, that won’t be hard to do.

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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?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This holiday home rental outside of Callicoon is located on a lake, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Callicoon?

With 15 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 River and Delaware River are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Villa Roma Driving Range and Big Island.

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.