Photo by Matthew Jay

Search Inns in Callicoon from CA $205

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Callicoon Inns

The Settlers Inn
Property grounds

The Settlers Inn

3.5 star property
9.4 out of 10, Exceptional, (233)
"Friendly staff and comfortable stay."
The price is CA $253
CA $340 total
includes taxes & fees
May 6 - May 7
The Settlers Inn
Upstate Inn Monticello
Double Room, Multiple Beds, Non Smoking, Private Bathroom

Upstate Inn Monticello

3.0 star property
7.0 out of 10, Good, (40)
"There were no mirrors in the bathroom or in the room."
The price is CA $205
CA $232 total
includes taxes & fees
May 3 - May 4
Upstate Inn Monticello
The North Branch Inn
Property grounds

The North Branch Inn

4.0 star property
9.6 out of 10, Exceptional, (28)
"The place was charming and immaculate. It was so tastefully decorated with all the amenities. Breakfast was delicious, modern cuisine. Jake and Caroline were so welcoming, friendly and accommodating. We intend to return for a whole weekend very soon."
The price is CA $325
CA $411 total
includes taxes & fees
May 8 - May 9
The North Branch Inn
Roscoe Mountain Club
Standard Double Room

Roscoe Mountain Club

3.0 star property
9.6 out of 10, Exceptional, (62)
"This place was great! Only thing it’s missing is an indoor pool then it’d be 10/10"
The price is CA $303
CA $343 total
includes taxes & fees
May 1 - May 2
Roscoe Mountain Club
The Yarra
Free daily continental breakfast

The Yarra

4.0 star property
10.0 out of 10, Exceptional, (22)
"Beautiful place"
The price is CA $329
CA $372 total
includes taxes & fees
May 1 - May 2
The Yarra
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.
Don't see what you're looking for?
See all available properties in Callicoon
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Callicoon

Postcard Cabins Western Catskills
Exterior

Postcard Cabins Western Catskills

2.0 star property
9.8 out of 10, Exceptional, (6)
"They had excellent communication, it was easy to get to the cabin and door key pad worked great. It was very clean, the floors are industrial carpeted, so I recommend bringing slippers or house shoes so you aren’t wearing your shoes inside. The water pressure on the shower was minimal- which can be expected when glamping- so don’t expect to take a long hot shower and wash your hair. Remember you are comfort camping :) the little extras were great! S’mores kit, hot cocoa, tea, water, etc. "
The price is CA $187
CA $259 total
includes taxes & fees
May 1 - May 2
Postcard Cabins Western Catskills
Handcrafted Riverfront Cabin on 10 acres
Exterior

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (151)
"Great cabin exactly as advertised. Go ahead and book it you won’t be disappointed. "
The price is CA $171
CA $458 total
includes taxes & fees
May 14 - May 15
Handcrafted Riverfront Cabin on 10 acres
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
5 bedrooms, desk, iron/ironing board, free WiFi

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

9.0 out of 10, Wonderful, (73)
"We had an amazing stay at this property! Everything was exactly as described—clean, comfortable, and beautifully maintained. It felt like a true home away from home. The location was perfect, and all the amenities were thoughtfully provided.What really stood out was how smooth and stress-free the whole process was. Communication with the owner was excellent from start to finish—quick responses, clear instructions, and super helpful throughout. It made the entire experience even better.Highly...
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
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.

Frequently asked questions

Why book your Callicoon inn with Expedia?
Booking an inn in Callicoon is as simple as deciding on your travel dates and selecting an option that meets your requirements. Chasing something luxurious or low cost, or a property that also comes with a pool and a restaurant? Use Expedia’s search filters to further narrow your search results and find your dream fit.
How can I find cheap Callicoon inns?
Expedia’s filters make it a snap to find cheap Callicoon inns. Tailor your search results by your budget and preferred star rating — lower-rated properties are lighter on your hip pocket. You can also sign up for Expedia Rewards for free to access awesome bargains on your ideal inn.