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

Callicoon Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Callicoon vacation 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 traveler
$451 nightly
The price is $508
Sep 29 - Sep 30
Total with taxes and fees
Bright Modern Home * Wood-Stove Nights * Big Deck
A camper van parked at night with a campfire in front, surrounded by wooden furniture and trees.

2. 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.
$245 nightly
The price is $275
Sep 28 - Sep 29
Total with taxes and fees
Glamping in Vintage Airstream with modern comforts with private pond access.
A house surrounded by trees and a river.

3. Callicoon Creek Farmhouse

Callicoon Creek Farmhouse
Callicoon
9.4 out of 10, Exceptional, (11 reviews)
"In town for a family gathering. House was perfect for our needs. Will recommend"
United States
Tom B.
$295 nightly
The price is $332
Sep 27 - Sep 28
Total with taxes and fees
Callicoon Creek Farmhouse
A wooden cabin with a sloped roof, a central door, and two hanging hammocks.

4. Property of Big Foot Roscoe, NY

Property of Big Foot Roscoe, NY
Roscoe
9.8 out of 10, Exceptional, (9 reviews)
"Quiet place with fantastic hosts!"
United States
Jeremy H.
$121 nightly
The price is $136
Sep 29 - Sep 30
Total with taxes and fees
Property of Big Foot Roscoe, NY
A wooden cabin with a kitchen and a bed, surrounded by trees.

5. 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, (195 reviews)
"Place was very quiet and it has a beautiful view"
United States
Leandro
$149 nightly
The price is $164
Sep 28 - Sep 29
Total with taxes and fees
Postcard Cabins Western Catskills, Outdoor Collection by Marriott Bonvoy
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, (23 reviews)
"Great stay!"
United States
melissa m.
$203 nightly
The price is $228
Sep 30 - Oct 1
Total with taxes and fees
Lakeview Cabin Duplex
A cabin with a triangular roof, a deck, and a fire pit with chairs.

7. BirchRidge A-Frame:Catskills Retreat-Sauna-Firepit

BirchRidge A-Frame:Catskills Retreat-Sauna-Firepit
Jeffersonville
10.0 out of 10, Exceptional, (1 review)
$437 nightly
The price is $492
Sep 30 - Oct 1
Total with taxes and fees
BirchRidge A-Frame:Catskills Retreat-Sauna-Firepit
A modern interior with a wooden staircase, a seating area with a bench, and a view through large glass doors to an outdoor patio.

8. Suite 001 Summary:<br>Th

Suite 001 Summary:<br>Th
Kenoza Lake
10.0 out of 10, Exceptional, (1 review)
"The experience was amazing. It was a very relaxing and restful weekend. The staff was beyond accommodating and the restaurant in the property provided amazing tasting meals. The amenities all worked and were a great pleasure. I will definitely be visiting this property again. "
United States
Stefan W.
$399 nightly
The price is $435
Sep 27 - Sep 28
Total with taxes and fees
Suite 001 Summary:<br>Th
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.
$222 nightly
The price is $250
Sep 28 - Sep 29
Total with taxes and fees
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, (118 reviews)
"We had a wonderful one night stay!"
United States
Anonymous traveler
$293 nightly
The price is $330
Oct 4 - Oct 5
Total with taxes and fees
In the cloud ~your cozy lake house
A modern building with a stone wall and a fire pit in the foreground.

11. FOUNDERS COTTAGE - 2 room with kitchennete

FOUNDERS COTTAGE - 2 room with kitchennete
Kenoza Lake
$424 nightly
The price is $464
Sep 27 - Sep 28
Total with taxes and fees
FOUNDERS COTTAGE - 2 room with kitchennete
A hot tub in a wooden deck with large windows overlooking a grassy area.

12. 1930's Vintage Cabin · Hot Tub · Kohler Cabin

1930's Vintage Cabin · Hot Tub · Kohler Cabin
Jeffersonville
9.6 out of 10, Exceptional, (5 reviews)
"The Kohler Cabin was an absolute pleasure! The amenities were pristine and the area is wonderful! Plenty of space, with fun games, great kitchen, super hip record player. More than just a stay, it was an experience. Would definitely go back!"
United States
MichaelW
$446 nightly
The price is $494
Oct 4 - Oct 5
Total with taxes and fees
1930's Vintage Cabin · Hot Tub · Kohler Cabin
A modern interior with a staircase, a seating area, and a view through large windows.

13. Coop 002

Coop 002
Kenoza Lake
$375 nightly
The price is $408
Sep 28 - Sep 29
Total with taxes and fees
Coop 002
A fire pit with logs, surrounded by rocks and gravel, with two red chairs and a tree stump nearby.

14. 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
$213 nightly
The price is $239
Sep 27 - Sep 28
Total with taxes and fees
Roscoe Cottage Pet Friendly
A spacious living room with a white sofa, a glass coffee table, and a fireplace.

15. Waterfront Lake House Retreat with Kayaks and Bikes

Waterfront Lake House Retreat with Kayaks and Bikes
Lake Huntington
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful place to get away unplug and relax. The property was exactly as pictured, super clean, and so comfortable. The host provided everything we could need and the lake was perfect! Highly recommend! We had 6 adults comfortably stay for a long weekend."
United States
Greta V.
$702 nightly
The price is $791
Oct 1 - Oct 2
Total with taxes and fees
Waterfront Lake House Retreat with Kayaks and Bikes
A living room with a wooden floor, a sofa, a dining table with chairs, and a door leading outside.

16. 5 minutes from original Woodstock site.

5 minutes from original Woodstock site.
Mongaup Valley
9.8 out of 10, Exceptional, (75 reviews)
"The house was really nice. Decorated in line with the area. Plus, Bruce was a great host."
United States
Robert
$332 nightly
The price is $374
Sep 29 - Sep 30
Total with taxes and fees
5 minutes from original Woodstock site.

17. 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.
$216 nightly
The price is $243
Sep 29 - Sep 30
Total with taxes and fees
Cozy Farm Private Artistic Eclectic Cabin - 183 beautiful acres
A wooden house with a green roof, large windows, and a porch.

18. Luxury Catskills Creekside Cabin | Pool, Sauna & Fire Pit Retreat

Luxury Catskills Creekside Cabin | Pool, Sauna & Fire Pit Retreat
Roscoe
$427 nightly
The price is $485
Sep 28 - Sep 29
Total with taxes and fees
Luxury Catskills Creekside Cabin | Pool, Sauna & Fire Pit Retreat
A compact kitchen with a sink, a stove, and cabinets.

19. 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
$165 nightly
The price is $182
Sep 27 - Sep 28
Total with taxes and fees
Cozy Camper at Roscoe Wildlife Retreat
A campfire with logs and a candle on a table, surrounded by chairs, with a grill and a bottle of fuel nearby.

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.
$197 nightly
The price is $222
Sep 29 - Sep 30
Total with taxes and fees
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

Hampton Inn Monticello

Hampton Inn Monticello

10/10 Excellent
"It was great"
Tamta 1-night trip
Posted 1 hour ago
Hampton Inn Monticello

Find out more about Callicoon

Everything you need to know about Callicoon vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Callicoon vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Callicoon vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Callicoon vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Callicoon. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Callicoon in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $160 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Callicoon rentals

At Expedia, we put the best Callicoon vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Callicoon rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Callicoon vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Callicoon. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Callicoon?

Yes, we give you a choice of vacation rentals close to top local attractions in Callicoon, or you can choose a more secluded option if you're looking for relaxation. Callicoon is known for its entertainment choices and gardens.

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

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This vacation home rental near Callicoon is located on a lake and has an outdoor pool, a balcony, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Callicoon?

With 16 Expedia vacation rentals, you're sure 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 Villa Roma Go Kart Track.

What’s a vacation rental in Callicoon like?

A vacation rental is a private property where you can stay for short or long periods in Callicoon. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.