Callicoon Vacations from $560

Book a Hotel + Flight or Car together to unlock savings

Photo by Matthew Jay

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Callicoon vacation packages

Price found within the past 48 hours. Click for updated prices.
THE DARBY

THE DARBY

2 out of 5
Price was $722, price is now $560 per person
$560
per person
Oct 31 - Nov 4
just found
Roundtrip non-stop flight included
Philadelphia (PHL) to Wilkes-Barre (AVP)
8.2/10 Very Good! (52 reviews)
Stayed after a BethelWoods concert. Property and rooms very clean. Bed was comfortable. Would stay again!

Reviewed on Jul 22, 2025

The Willowbrook Golf Hotel At Split Rock

The Willowbrook Golf Hotel At Split Rock

2.5 out of 5
Save 100% on your flight
Price was $1,013, price is now $740 per person
$740
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) to Wilkes-Barre (AVP)
7.4/10 Good! (89 reviews)
We have stayed here at least once a year for the last 15 years and have always had a great experience. I was a little disappointed that I didn't really have hot water for a shower and there was no hair dryer or safe in the room this time. I definitely will come back as even these little things do not change the way I feel about the property.

Reviewed on Jul 21, 2025

Split Rock Resort

Split Rock Resort

3 out of 5
Price was $1,110, price is now $820 per person
$820
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Wilkes-Barre (AVP)
6.2/10 (1,010 reviews)
Beds and pillows were so comfy! The room was stifling when we first arrived but the AC after it was turned on helped. We left shortly and coming back at night, the room was perfect. The hallways were slightly moldy smelling and can be creepy early morning or late night. That said, I would stay again for a night or two (not alone though - my imagination would get the best of me)

Reviewed on Aug 22, 2025

Cozy Pocono Mountain Escape

Cozy Pocono Mountain Escape

3 out of 5
Save 100% on your flight
Price was $1,375, price is now $1,031 per person
$1,031
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Wilkes-Barre (AVP)
9.8/10 Exceptional! (37 reviews)
So peaceful. Able to explore trails in area. Quiet and friendly condo community. Owners are very helpful. Definitely would come back this time of year.

Reviewed on Jun 7, 2025

Twin Waters by Avantstay Patio + Pool Table

Twin Waters by Avantstay Patio + Pool Table

3 out of 5
Save 100% on your flight
Price was $1,791, price is now $1,352 per person
$1,352
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) to Wilkes-Barre (AVP)
10/10 Exceptional! (2 reviews)
The House was really good, the lake and pool are was amazing, my kids enjoy the gaming room and the living space area.

Reviewed on Aug 17, 2025

Don't see what you're looking for?
See all available trips from Columbus to Callicoon
View all trips

Callicoon Hotel Deals

Villa Roma Resort and Conference Center

Villa Roma Resort and Conference Center

3 out of 5
356 Villa Roma Rd, Callicoon, NY
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $203 total per night from Sep 3 to Sep 4
$203 total
Sep 3 - Sep 4
Total with taxes and fees
6.4/10 (352 reviews)
"While the overall property has an air of 50s charm it really needs an updo. The staff was the shining star. Lovely and helpful. The room was terrible with an actual key for the door. They seemed to be redoing some rooms near that one so here’s to hoping that room was next. The parking is a bit inconvenient ..."

Reviewed on Aug 11, 2025

Villa Roma Resort and Conference Center
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
555 Resorts World Drive, Monticello, NY
$216 nightly
The price is $244 total per night from Sep 7 to Sep 8
$244 total
Sep 7 - Sep 8
Total with taxes and fees
8/10 Very Good! (1,657 reviews)
"Na"

Reviewed on Aug 21, 2025

The Kartrite Resort & Indoor Waterpark
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
888 Resorts World Drive, Monticello, NY
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $188 total per night from Aug 27 to Aug 28
$188 total
Aug 27 - Aug 28
Total with taxes and fees
8.6/10 Excellent! (1,015 reviews)
"Was a clean and nice hotel."

Reviewed on Aug 20, 2025

Resorts World Catskills Casino
See all 1,086 properties in Callicoon
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Callicoon vacation package cost?
You can snap up a vacation package to this destination from $560 on Expedia. However, how much your vacation to Callicoon costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Callicoon?
If you're hoping to snag a cheap Callicoon vacation package, consider planning a trip in September, October and November. You'll generally find better prices on flights and accommodations during these months — ideal for budget-conscious travelers.
How many days is enough for Callicoon?
The ideal duration for your Callicoon vacation depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to check out all the major attractions and explore some hidden treasures along the way.
How to find the best Callicoon package deals?
Begin your search for a Callicoon package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Callicoon package deal straight away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Callicoon escape underway.
Is it cheaper to book a Callicoon vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Callicoon vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Callicoon?
If you've got your Callicoon vacation dates confirmed, book as soon as you can to score some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Callicoon vacation packages?
Your Callicoon trip is meant to be an escape from your busy life, not a reason for money worries. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.