Bearsville Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

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

  • Rest easy

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

Your Bearsville Vacation

Say farewell to planning hassles and hello to a Bearsville vacation package. With the finer details organized before you take off, you can focus on discovering the best of this city, starting with Kingston Stockade District, which is great for families, festivals and markets. Overlook Mountain Trailhead, Bethel Woods Museum and Ashokan Rail Trail- Woodstock Dike Trailhead are just some of the attractions worth checking out during your trip to Bearsville. A few quick clicks is all it takes to create the ideal Bearsville vacation on Expedia.

Bearsville Hotel Deals

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville NY
9.8/10 Exceptional! (89 reviews)
Absolutely stunning cabin!

Reviewed on Jan 6, 2026

Get rates
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
$169 nightly
The price is $183 total per night from Feb 2 to Feb 3
$183 total
Feb 2 - Feb 3
Total with taxes and fees
9.4/10 Exceptional! (137 reviews)
The room was better than expected. Simple but everything you needed was there. Looking forward to our next stay :)

Reviewed on Jan 25, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $138 total per night from Mar 1 to Mar 2
$138 total
Mar 1 - Mar 2
Total with taxes and fees
8.8/10 Excellent! (833 reviews)
Have stayed here many times. they have done a really good job of keeping the property up to date. Very nice people.

Reviewed on Jan 25, 2026

Residence Inn by Marriott Kingston
See all 2,449 properties in Bearsville
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 Bearsville Vacation Packages

Bearsville Essential Information

Language
English
Currency
U.S dollars
Top Sights
Ulster Performing Arts Center, Mount Tremper Arts and James Cox Gallery

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 Bearsville vacation package cost?
You can grab a vacation package to this destination on Expedia. However, how much your vacation to Bearsville costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Bearsville?
November, December and January are the best times to look for cheap Bearsville vacation packages. Traveling in quieter periods means you can generally find better prices on accommodations and flights.
How many days is enough for Bearsville?
With a well-planned schedule, you can easily hit the main Bearsville attractions in a handful of days. But if you prefer to discover hidden gems or go on day trips, consider booking your Bearsville vacation for longer.
How to find the best Bearsville package deals?
Start your search for a Bearsville package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Bearsville package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Bearsville escape underway.
Is it cheaper to book a Bearsville vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still have the flexibility to create a customized Bearsville vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Bearsville?
Secure incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Bearsville adventure.
Does Expedia offer Book Now, Pay Later Bearsville vacation packages?
Set off on your dream getaway to Bearsville with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait until your next payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.