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Callicoon Vacation Rentals

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Vacation Rentals in Callicoon

Equestrian House Suites

3.0 star property
Pleasant Mount
$538 nightly
The price is $587
Nov 23 - Nov 24
Total with taxes and fees
Equestrian House Suites

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Monticello
9.0 out of 10, Wonderful, (86)
"Great property for a group trip. We enjoyed the house it was spacious and had everything we needed. The lake, kayaks and paddle boards were a lot of fun. I highly recommend and would stay again."
United States
Denise D.
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Handcrafted Riverfront Cabin on 10 acres

Starlight
10.0 out of 10, Exceptional, (177)
"Beautiful cabin on very nice property. Great place to just relax. "
United States
Mary P.
$262 nightly
The price is $285
Nov 16 - Nov 17
Total with taxes and fees
Handcrafted Riverfront Cabin on 10 acres

Property of Big Foot Roscoe, NY

2.0 star property
Roscoe
10.0 out of 10, Exceptional, (7)
"Very nice"
United States
Mike R.
Property of Big Foot Roscoe, NY

Luxurious Glamping Dome Oasis in the Heart of The Catskills, 1.5 HR from NYC.

Parksville
9.8 out of 10, Exceptional, (31)
"Beautiful spot with cozy lodgings and thoughtful host. Would definitely stay again! "
United States
Taylor F.
Luxurious Glamping Dome Oasis in the Heart of The Catskills, 1.5 HR from NYC.

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

Narrowsburg
10.0 out of 10, Exceptional, (134)
"Loved the cabin, location and ability to enjoy nature!"
United States
Dave H.
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

A river runs through it

East Branch
10.0 out of 10, Exceptional, (18)
"This house was everything we were hoping for out of our trip to the Catskill Region of NY. Sitting on the banks of the river the house offered great views of the surrounding hills and water, all while staying cozy indoors with an amazing fireplace and very cool vibes. The property was well kept and the host was very friendly and accommodating to us. We will definitely be returning to stay at this house in the future."
United States
Ty M.
A river runs through it

Secluded modern log cabin with picturesque private water fall on 12 acres!

Roscoe
10.0 out of 10, Exceptional, (132)
"We thoroughly enjoyed ourselves. We took a walk to the waterfalls, went shopping, and went to Roscoe Beer Works. It was a perfect spot to escape reality fir a weekend and catch uo with best friends!!"
United States
Lara L.
Secluded modern log cabin with picturesque private water fall on 12 acres!

Highland Group/Family Estate! 5 Private Units, Pool, Hotub, Gameroom; 40+ guests

2.0 star property
Monticello
8.0 out of 10, Very Good, (4)
"We had the BEST time staying here with our sorority sisters! The property is absolutely perfect for groups — so many private bedrooms that gave everyone their own space, plus the cutest houses and cabins that made it feel like a little village just for us. The dining hall was super chill and such a great hangout spot for meals and late-night laughs.We loved how close it was to everything — food, fun activities, and plenty of outdoor space to enjoy the yard. It made planning so easy since...
United States
Nancy D.
Highland Group/Family Estate! 5 Private Units, Pool, Hotub, Gameroom; 40+ guests

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Monticello
9.6 out of 10, Exceptional, (49)
"The view was beautiful and the house was spotless. They had extra amenities that we forgot so we were set for our trip! Amazing owner who is very sweet and thoughtful!"
United States
Kayla U.
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Luxury 8BR Lodge w/ Heated Indoor Pool • Game Room • Near Lake Wallenpaupack

2.0 star property
Honesdale
Luxury 8BR Lodge w/ Heated Indoor Pool • Game Room • Near Lake Wallenpaupack

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

Lake Como
10.0 out of 10, Exceptional, (189)
"We really enjoyed our stay! Jim and Tracy were fantastic and very nice! The cabin is so peaceful. If, you are looking for a peaceful getaway this is the place to go to! You will love it!"
United States
Alexis M.
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

Tiny House Cabin in Livingston Manor, NY

Livingston Manor
6.0 out of 10, (3)
"access for an after dark arrival unsafe and dangerous for other than truck. No locks on doors, very isolated for two young females. Long walk on narrow unlit path after leaving vehicle. (75 yards) host cordial. and gracious about cancellation. confusion about which unit would be used. "
United States
Gretchen F.
$200 nightly
The price is $225
Nov 14 - Nov 15
Total with taxes and fees
Tiny House Cabin in Livingston Manor, NY

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

Lakewood
9.6 out of 10, Exceptional, (122)
"We loved the privacy and enjoyed all the kayaks, boat and canoe. Perfect lake vacation, plan on making it a yearly trip."
United States
CINDY M.
$372 nightly
The price is $404
Nov 15 - Nov 16
Total with taxes and fees
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

Breathtaking 44+ Acre Country Estate

Pleasant Mount
10.0 out of 10, Exceptional, (36)
"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"
United States
Michael S.
Breathtaking 44+ Acre Country Estate

Hideaway!! less than a mile to the acres

Equinunk
10.0 out of 10, Exceptional, (11)
"We enjoyed our stay. The place was quiet, cozy, and well equipped, and Charlie was responsive to our questions."
United States
Philip
$244 nightly
The price is $264
Nov 14 - Nov 15
Total with taxes and fees
Hideaway!! less than a mile to the acres

Domes at Catskills

3.5 star property
Swan Lake
10.0 out of 10, Exceptional, (6)
"The most amazing weekend we ever had! What a beautiful place and property! We were left speechless and cannot wait to come back! Everything was top notch, the space, the design, the furniture, the kitchen, the patio and outdoor space. Very friendly staff and prompt service. Highly recommend for an excellent couple getaway. "
United States
Anonymous traveler
Domes at Catskills

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

Forestburgh
10.0 out of 10, Exceptional, (9)
"Lovely property in a serene and interesting setting. The hosts were so kind and communicative. We stayed for a night and enjoyed local sights and a concert in Bethel! "
United States
Erin
$290 nightly
The price is $326
Nov 15 - Nov 16
Total with taxes and fees
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

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

Beach Lake
9.6 out of 10, Exceptional, (230)
"Amazing cabin trip with the family! We will definitely be back to this place! "
United States
Tyler
Experience Delaware Riverfront cabin nestled in the woods, Pet/Family Friendly

Heaven Lane! Heaven it is! Sleeps 15

Honesdale
10.0 out of 10, Exceptional, (89)
"All 13 of us had a great week!!!"
United States
Michael G.
Heaven Lane! Heaven it is! Sleeps 15
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

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 $186 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.

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 fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Callicoon?

With 19 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 Big Island 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.