Bearsville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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.
Ready to book your vacation to Bearsville?
Bearsville Hotel Deals
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
CA $210
CA $237 total
Aug 16 - Aug 17
includes taxes & fees
8.2/10 Very good! (973 reviews)
"Charming, and Historic!!"
Reviewed on Aug 14, 2026
Hunter Lodge, a Bluebird by Lark
7433 Main St Hunter NY
Fully refundableReserve now, pay when you stay
CA $176
CA $220 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"The hotel has made upgrades to make the interior look like a lodge. However there was a horrible smell around the back of the property so you could not even sit and enjoy the fire pit or the scenery. My bed must have had a broken boxspring because it kept creaking and then I noticed it was giving ..."
Reviewed on Aug 14, 2026
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
282 Cairo Junction Rd Catskill NY
CA $223
CA $301 total
Sep 13 - Sep 14
includes taxes & fees
9.6/10 Exceptional! (273 reviews)
"Beautiful place it’s amazing pace full very nice"
Reviewed on Aug 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.
Frequently asked questions
How much does a Bearsville vacation package cost?
You'll find cheap prices on Expedia for your Bearsville getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Bearsville costs.
What are the cheapest months to go to Bearsville?
Plan your getaway for the low season and you're likely to score cheap Bearsville vacation packages. Remember that school vacation periods and major local events can impact prices, so do your research before you go.
How many days is enough for Bearsville?
To fully enjoy your Bearsville vacation, we recommend staying for 3 days. Divide your time between visiting Karma Triyana Dharmachakra Monastery, Woodstock Music Shop and other top attractions, in addition to exploring neighbourhoods like Zena and West Hurley. If you've got some time to spare, add a day trip or tour to your Bearsville vacation itinerary.
How to find the best Bearsville package deals?
Start your search for a Bearsville package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Bearsville package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Bearsville adventure off to a flying start.
Is it cheaper to book a Bearsville vacation as a package?
You can enjoy significant savings on your next Bearsville retreat by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to see some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
How to plan a trip to Bearsville?
- Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Bearsville.
- Work out your budget: Make sure you have enough money to pay for everything from transportation and food to activities and flights. Your accommodations will probably be the biggest expense during your trip to Bearsville.
- Decide your trip length: Think about how much time you want to spend discovering Bearsville. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Bearsville vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
