Bearsville Vacations from $1,247

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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.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Save 100% on your flight
Price was $1,611, price is now $1,247 per person
$1,247
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
8.8/10 Excellent! (97 reviews)
Family Weekend Getaway. This is our 4th time at this property. Our first time was a year ago during Memorial Day Weekend. Although it was a very droopy weekend, Wylder made it an unforgettable moment . Enough to come back several times. May 16 weekend was one if the best, the weather was perfect, the food as always delicious and the staff amazing. Wylder will always be a perfect location with or without kids/furry babies . I am all ready looking for our next weekend getaway.

Reviewed on May 18, 2026

Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

3 out of 5
Save 100% on your flight
Price was $17,810, price is now $12,232 per person
$12,232
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
No reviews
The Haüs Windham

The Haüs Windham

2 out of 5
Save 100% on your flight
Price was $1,987, price is now $1,414 per person
$1,414
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
7.8/10 Good! (28 reviews)
I stayed in the mirror cabin everything was great just prepare to have no microwave and or a burner. So you cannot cook or heat anything up. I was able to make it work by just getting stuff that can be eaten cold and then going out to dinner which was fine. Also because the cabin is mirror please note birds constantly fly into it on purpose. It was one bird that every day i was there from morning to night was hitting the glass and it did get very annoying.

Reviewed on Apr 20, 2026

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Bearsville Hotel Deals

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville NY
10/10 Exceptional! (131 reviews)
"Our girl's weekend group of 7 fit perfectly in this beautiful property. Valerie is a very welcoming and responsive host. The property is comfortable, clean and has a very well-appointed kitchen. The unique vibe of Woodstock and the towns of Kingston and Saugerties made for fun browsing and dining. ..."

Reviewed on May 19, 2026

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Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave Kingston NY
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $134 total per night from Jun 2 to Jun 3
$134 total
Jun 2 - Jun 3
Total with taxes and fees
7.4/10 Good! (1,007 reviews)
"Room was very clean and comfortable"

Reviewed on May 25, 2026

Best Western Plus Kingston Hotel And Conference Center
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St Hunter NY
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $149 total per night from Jun 7 to Jun 8
$149 total
Jun 7 - Jun 8
Total with taxes and fees
9.2/10 Wonderful! (950 reviews)
"Not worth the money"

Reviewed on May 25, 2026

Hunter Lodge, a Bluebird by Lark
See all 2,486 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

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Frequently asked questions

How much does a Bearsville vacation package cost?
You can grab a vacation package to this destination from $1,247 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.