Bearsville Vacations from $551
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
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.
The Latest Bearsville vacation packages
Price found within the past 48 hours. Click for updated prices.
Bearsville Hotel Deals
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$152 nightly
$172 total
Sep 27 - Sep 28
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
"The bartender she is excellent"
Reviewed on Sep 26, 2026
Hunter Lodge, a Bluebird by Lark
7433 Main St Hunter NY
Fully refundableReserve now, pay when you stay
$155 nightly
$168 total
Oct 25 - Oct 26
Total with taxes and fees
9.2/10 Wonderful! (1,017 reviews)
"Just for starters, our room was very very clean and very nice. Lots of room comfortable, bed. I guess some of the problems were with the outside areas. We noticed outside our patio, a pile of cigarette butts and roaches, and some chipping paint that didn’t appear to have been cleaned up for a while. ..."
Reviewed on Sep 26, 2026
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
282 Cairo Junction Rd Catskill NY
$201 nightly
$217 total
Oct 26 - Oct 27
Total with taxes and fees
9.6/10 Exceptional! (309 reviews)
"Excellent place"
Reviewed on Sep 25, 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 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
Frequently asked questions
How much does a Bearsville vacation package cost?
You can grab a vacation package to this destination from $551 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.
