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

Callicoon Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Callicoon holiday rentals

A wooden deck with Adirondack chairs and a small table, overlooking a garden.

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 HK$1,043
HK$4,434 total
includes taxes & fees
27 Oct - 28 Oct
Bright Modern Home * Wood-Stove Nights * Big Deck
A house surrounded by trees and a river.

2. Callicoon Creek Farmhouse

Callicoon Creek Farmhouse
Callicoon
9.4 out of 10, Exceptional, (14 reviews)
"In town for a family gathering. House was perfect for our needs. Will recommend"
United States
Tom B.
The price is HK$980
HK$2,732 total
includes taxes & fees
28 Oct - 29 Oct
Callicoon Creek Farmhouse
A wooden cabin with a kitchen and a bed, surrounded by trees.

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, (210 reviews)
"Such a beautiful cabin, I will call it as glamping. Location was perfect. I would love to go one more time"
United States
Pallavi
The price is HK$926
HK$1,363 total
includes taxes & fees
2 Nov - 3 Nov
Postcard Cabins Western Catskills, Outdoor Collection by Marriott Bonvoy
A cabin with a wooden deck and a staircase leading to a second-story balcony.

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, (167 reviews)
"Such a beautiful place to stay and explore with my pup!"
United States
Alison H.
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
A wooden cabin with a sloped roof, a central door, and two hanging hammocks.

5. 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 HK$790
HK$1,062 total
includes taxes & fees
27 Oct - 28 Oct
Property of Big Foot Roscoe, NY
A house with a dock by a lake, surrounded by trees and a clear sky.

6. Lakeview Cabin Duplex

Lakeview Cabin Duplex
Lake Huntington
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!"
United States
melissa m.
The price is HK$1,003
HK$1,824 total
includes taxes & fees
27 Oct - 28 Oct
Lakeview Cabin Duplex
A camper van parked at night with a campfire in front, surrounded by wooden furniture and trees.

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 HK$1,763
HK$2,638 total
includes taxes & fees
25 Oct - 26 Oct
Glamping in Vintage Airstream with modern comforts with private pond access.
A deck with lounge chairs and an umbrella, overlooking a body of water and a building with a blue exterior.

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 HK$925
HK$3,410 total
includes taxes & fees
27 Oct - 28 Oct
Victorian Lake Oasis | Hot Tub | Private Lakefront
A wooden deck with wicker furniture and a white railing.

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 HK$1,324
HK$2,176 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2-bedroom cabin in serene Lake Huntington with AC
A circular outdoor seating area with wooden chairs and a central table, surrounded by a stone-paved circle.

10. In the cloud ~your cozy lake house

In the cloud ~your cozy lake house
Swan Lake
9.6 out of 10, Exceptional, (120 reviews)
"We had a wonderful one night stay!"
United States
Anonymous traveller
The price is HK$1,397
HK$2,733 total
includes taxes & fees
26 Oct - 27 Oct
In the cloud ~your cozy lake house
A gym with a weight machine, a mirror, and a door.

11. 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 HK$494
HK$949 total
includes taxes & fees
25 Oct - 26 Oct
Charming 1 bedroom apartment with AC in quaint Roscoe
A snow-covered landscape with a building labeled "Trout Town Inn" and a covered outdoor area with trees.

12. Catskills Adventures

Catskills Adventures
Roscoe
9.0 out of 10, Wonderful, (12 reviews)
"Very clean easy access from freeway. "
United States
kevin
The price is HK$1,058
HK$1,656 total
includes taxes & fees
25 Oct - 26 Oct
Catskills Adventures
A restaurant interior with a dining table set for two, featuring a plate of food, a glass of water, and a martini glass.

13. Mountaintop Hideaway ~ Piece of Paradise - Apt

Mountaintop Hideaway ~ Piece of Paradise - Apt
Honesdale
9.0 out of 10, Wonderful, (30 reviews)
"Out stay was terrific all was enjoyable"
United States
Vincent W.
The price is HK$614
HK$1,348 total
includes taxes & fees
27 Oct - 28 Oct
Mountaintop Hideaway ~ Piece of Paradise - Apt
A small wooden cabin with a sloped roof, a door, and two hammock-style seating areas.

14. Roscoe Coop Clucking Crazy Hut

Roscoe Coop Clucking Crazy Hut
Roscoe
10.0 out of 10, Exceptional, (11 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 HK$748
HK$1,014 total
includes taxes & fees
27 Oct - 28 Oct
Roscoe Coop Clucking Crazy Hut
A porch with a bench, a door with a wreath, and a welcome mat.

15. The Little Hayloft - Clean & Bright One Bedroom Loft in Honesdale, PA

The Little Hayloft - Clean & Bright One Bedroom Loft in Honesdale, PA
Honesdale
10.0 out of 10, Exceptional, (62 reviews)
"Amazing property! We were so pleasantly surprised in person how cute, spacious, and clean it was! We were in town for a wedding and had an amazing stay ! "
United States
Victoria N.
The price is HK$910
HK$1,610 total
includes taxes & fees
25 Oct - 26 Oct
The Little Hayloft - Clean & Bright One Bedroom Loft in Honesdale, PA
A fire pit with logs, surrounded by rocks and gravel, with two red chairs and a tree stump nearby.

16. 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 HK$1,234
HK$1,916 total
includes taxes & fees
26 Oct - 27 Oct
Roscoe Cottage Pet Friendly
A campfire with logs and a candle on a table, surrounded by chairs, with a grill and a bottle of fuel nearby.

17. 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 HK$1,312
HK$1,827 total
includes taxes & fees
27 Oct - 28 Oct
Roscoe RV Pet Friendly
A two-story house with a stone chimney, a front porch with white railings, and a well-maintained lawn.

18. Private 5-Acre Farmhouse Retreat - Bethel Woods 25 min - Sleeps 8 - Pets Welcome

Private 5-Acre Farmhouse Retreat - Bethel Woods 25 min - Sleeps 8 - Pets Welcome
Livingston Manor
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed ourselves greatly! Very Nice Property, and Chalet Style Home with everything you need. We highly recommend staying here. And Mr. Pope was a great host."
United States
Robert
The price is HK$1,263
HK$2,617 total
includes taxes & fees
1 Nov - 2 Nov
Private 5-Acre Farmhouse Retreat - Bethel Woods 25 min - Sleeps 8 - Pets Welcome
A small wooden cabin with a sloped roof, a single door, and a hammock hanging inside.

19. 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 HK$940
HK$1,276 total
includes taxes & fees
25 Oct - 26 Oct
Woods I GO 2 Lose my Mind Roscoe
A cozy room with a stone wall, a large window, a blue cabinet, and a striped armchair.

20. River Views * Fireplace * Sunroom * Walk to Town

River Views * Fireplace * Sunroom * Walk to Town
Narrowsburg
10.0 out of 10, Exceptional, (9 reviews)
"This property was beautiful, comfortable, and clean. It has everything you need, but not so much it is overwhelming or cluttered. If I go back up again, I would definitely book this again."
United States
Audrey H.
The price is HK$914
HK$4,473 total
includes taxes & fees
26 Oct - 27 Oct
River Views * Fireplace * Sunroom * Walk to Town
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Callicoon Hotel Reviews

Best Western Monticello

Best Western Monticello

8/10 Good
"Muy bonito lugar. Me encantó la pasé muy bien con mi esposa y mi hija. Un sitio para descansar de la rutina del trabajo. Muy recomendado de verdad"
Mauricio 1-night trip
Posted 7 hours ago
Best Western Monticello

Find out more about Callicoon

Search for holiday rentals in Callicoon on Expedia! You can easily find your home rentals, villas, holiday apartments in Callicoon using one of the methods below:

  • View our selection of featured holiday rentals in Callicoon
  • Use the map to find apartments and other holiday homes in the Callicoon neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Callicoon while they last

Look no further and take a look at our great range of rental properties in Callicoon!

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.