Callicoon Vacations from $570
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Cove Haven Resort
$570
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Wilkes-Barre (AVP)
8.2/10 Very Good! (1,256 reviews)
The diversity of the patrons, young, older, different nationalities.
The food was very good and it's a nice short stay to rekindle feelings of love and passion
Reviewed on Oct 14, 2026
Crestline Retreat by Avantstay Luxury Mountain Condo Hot Tub + Game Room Steps to Big Boulder
$3,325
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Wilkes-Barre (AVP)
10/10 Exceptional! (1 review)
Me and my children take a family trip every year. We’ve made it a family tradition we like staying at Lake Harmony and Big Boulder and where I stayed this weekend was very nice. It’s very cozy very clean and neat and we had fun. I love the hot tub and will be back again. Thank you.
Reviewed on Mar 23, 2026
Estates Drive by Avantstay Pocono Cabin + Deck + Firepit Near Big Boulder & Jack Frost
Lake Harmony Estates
$2,672
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Wilkes-Barre (AVP)
8/10 Very Good! (3 reviews)
Handles on the bath had soap scum and the frying pans were dirty. Other than that the place was clean and comfortable.
Reviewed on Oct 2, 2026
Harmony Cottage by Avantstay Lake Access, Hot Tub, Fire Pit, & Game Room
Lake Harmony Estates
$2,344
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Wilkes-Barre (AVP)
9/10 Wonderful! (7 reviews)
Clean lovely area! House had issue with upstairs sink, water went down way to slow. Also no hot water in same sink.
Could use new carpet steps n upstairs. We had a great time, went to Jim Thorpe for the day… great, shopping, restaurants, railroad train ride. We’ll be back in Spring
Reviewed on Sep 27, 2026
Stay near popular Callicoon attractions
Villa Roma Driving Range
This pristine driving range offers a serene Catskills backdrop for perfecting your swing technique. Practice various shots while enjoying the peaceful mountain scenery of Villa Roma Golf Club.
Big Island
Commune with nature and explore the great outdoors at Big Island during your travels in Callicoon. Amble around the area's gardens or experience its entertainment venues.
Villa Roma Go Kart Track
You can take time to visit Villa Roma Go Kart Track during your travels to Callicoon. Amble around the area's gardens or experience its entertainment venues.
Callicoon Hotel Deals
Villa Roma Resort and Conference Center
356 Villa Roma Rd Callicoon NY
Fully refundableReserve now, pay when you stay
$185 nightly
$209 total
Oct 15 - Oct 16
Total with taxes and fees
The Kartrite Resort & Indoor Waterpark
555 Resorts World Drive Monticello NY
$270 nightly
$296 total
Oct 15 - Oct 16
Total with taxes and fees
8.2/10 Very Good! (2,464 reviews)
"We love the Kartrite and go every year. It’s clean, fun and always good food!"
Reviewed on Oct 14, 2026
Resorts World Catskills Casino
888 Resorts World Drive Monticello NY
Fully refundableReserve now, pay when you stay
$205 nightly
$228 total
Oct 21 - Oct 22
Total with taxes and fees
8.8/10 Excellent! (1,279 reviews)
"Great place to stay"
Reviewed on Oct 14, 2026
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 |
More vacations you might like
Frequently asked questions
How much does a Callicoon vacation package cost?
You can snap up a vacation package to this destination from $570 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.
Explore a world of travel with Expedia
- Wyndham Hotels in Roscoe
- Hotels in Callicoon
- 5 Star Hotels in Narrowsburg
- Villas in White Lake
- Best Western Hotels in Cochecton
- Privatevacationhomes in Lake Huntington
- Spa in Callicoon
- Hotels in Long Eddy
- Casino in Callicoon
- Hotels in North Branch
- Hotels in Narrowsburg
- Cabins in Callicoon
- Hotels in Jeffersonville
- Hotels in Bethel
- 3 Star Hotels in Callicoon
- Bedandbreakfast in Callicoon
- JetBlue Airways Orlando (MCO) to Newburgh (SWF) flights
- Flights to Kenoza Lake
- Flights to Cochecton
- Flights from Jamaica (JFK) to Monticello (MSV)
- Flights to Callicoon
- Flights to Bethel
- Delta Air Lines Atlanta (ATL) to Newburgh (SWF) flights
- Flights to Roscoe
- Flights from Fort Lauderdale (FLL) to Monticello (MSV)
- Flights to White Lake
- Visit Kenoza Lake
- Where to stay in Hudson Valley
- Where to stay in Newburgh
- Where to stay in Poughkeepsie
- Liberty Vacations
- The Catskills All Inclusive Vacation Packages
- Visit Swan Lake
- Parksville Vacations
- Bethel Woods Center
- Where to stay in Kerhonkson
- Where to stay in Roscoe
- Narrowsburg Vacations
- Where to stay in Narrowsburg
- The Catskills All Inclusive Vacation Packages
- Visit Callicoon
- Monticello Vacations
- Port Jervis Vacations
- Visit Monticello
- The Catskills All Inclusive Vacation Packages
- Where to stay in Liberty
- Mamakating Park Historic Vacations
- Visit Cochecton
- Visit Lake Huntington
- Debruce Vacations
- Where to stay in Port Jervis
- Visit Long Eddy
- Sundown Vacations
- The Catskills All Inclusive Vacation Packages
- Visit White Lake
- Visit South Fallsburg
- East Branch Delaware River
- Visit Liberty
- The Catskills All Inclusive Vacation Packages
- Where to stay in Monticello
- Visit Hancock
- The Catskills All Inclusive Vacation Packages
- Monticello Raceway
- The Catskills All Inclusive Vacation Packages
- The Catskills All Inclusive Vacation Packages
- Lake Superior State Park
- Where to stay in New Paltz
- Pine Island Vacations
- The Catskills All Inclusive Vacation Packages
- The Catskills All Inclusive Vacation Packages
- Resorts World Catskills
- Car rentals in Jeffersonville
- Hertz Rental Cars in Callicoon
- Car rentals in Liberty
- Car rentals in Narrowsburg
- Car rentals in Long Eddy
- Car rentals in Cochecton
- Standard Car Rentals in Callicoon
- Car rentals in Callicoon
- Economy Car Rentals in Deposit
- Van Car Rentals in Liberty
- Enterprise Rental Cars in Callicoon
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
