Callicoon Vacations from $342

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The Latest Callicoon vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

3 out of 5
Price was $353, price is now $342 per person
$342
per person
Mar 2 - Mar 6
found 21 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Wilkes-Barre (AVP)
8.4/10 Very Good! (1,003 reviews)
Well the place is clean the most good the staff are awesome. The room perfect, the amenities perfect, breakfast was delicious. The staff are awesome, made me feel right at home away from home. They have a couple of games fitness center too. Highly recommend

Reviewed on Jan 16, 2026

Cozy Pocono Mountain Escape

Cozy Pocono Mountain Escape

3 out of 5
Price was $750, price is now $540 per person
$540
per person
Mar 2 - Mar 6
found 21 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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

The Willowbrook Golf Hotel At Split Rock

The Willowbrook Golf Hotel At Split Rock

2.5 out of 5
Price was $506, price is now $367 per person
$367
per person
Mar 2 - Mar 6
found 21 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Wilkes-Barre (AVP)
7.4/10 Good! (99 reviews)
We chose the resort for the full kitchen in the unit. Everything was okay… but we were not wowed. We used the fitness room 4 days in a row. It seemed as though the place was under a transition. There was new equipment, but it was not fully setup. We had a hot tub in our room that served as a tub… the jets did not work. So many small things that could have been better. However the area was great and we enjoyed our stay. The breakfast attendant was excellent in keeping up with the flow of traffic, and the food was fresh.

Reviewed on Jan 1, 2026

Cove Haven Resort

Cove Haven Resort

3.5 out of 5
Price was $835, price is now $614 per person
$614
per person
Mar 2 - Mar 6
found 21 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Wilkes-Barre (AVP)
8.4/10 Very Good! (1,013 reviews)
Room was nice but facilities were a little old it’s time for them to upgrade. Besides that I had fun. The breakfast buffet was good but dinner was alright for the price.

Reviewed on Jan 27, 2026

Saddleview Bed & Breakfast

Saddleview Bed & Breakfast

3 out of 5
Price was $401, price is now $370 per person
$370
per person
Mar 2 - Mar 6
found 21 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Wilkes-Barre (AVP)
10/10 Exceptional! (12 reviews)
Friendly staff went above and beyond, breakfast was delish! Stuffed French toast was my fav!

Reviewed on Jan 26, 2026

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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
$121 nightly
The price is $137 total per night from Feb 11 to Feb 12
$137 total
Feb 11 - Feb 12
Total with taxes and fees
6.4/10 (394 reviews)
School trip. Got my own room

Reviewed on Jan 25, 2026

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
$250 nightly
The price is $283 total per night from Feb 1 to Feb 2
$283 total
Feb 1 - Feb 2
Total with taxes and fees
8/10 Very Good! (1,934 reviews)
Yes

Reviewed on Jan 28, 2026

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
$184 nightly
The price is $205 total per night from Feb 1 to Feb 2
$205 total
Feb 1 - Feb 2
Total with taxes and fees
8.6/10 Excellent! (1,115 reviews)
Staff was great

Reviewed on Jan 27, 2026

Resorts World Catskills Casino
See all 1,132 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.

Find the Best Callicoon Vacation Packages

Callicoon Essential Information

Language
English
Currency
U.S dollars
Population
170
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Lake Superior State Park, Fort Delaware Museum and Bethel Woods

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Frequently asked questions

How much does a Callicoon vacation package cost?
You can snap up a vacation package to this destination from $342 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.