Bearsville Vacations from $546

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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.
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Price was $692, price is now $546 per person
$546
per person
Dec 4 - Dec 7
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
9/10 Wonderful! (417 reviews)
We enjoyed an overnight stay at this Air Stream when we visited Kaaterskill Falls for our anniversary. Clean & spacious bathroom, nice to be able to take a hot shower after a full day hike. Kitchenette well equipped with mini fridge, microwave, electric kettle & dinnerware & utensils. Private picnic table & fire pit outside for campfire & cooking but you have to buy the firewood which wasn’t included in the resort fee. Had dinner at the clubhouse kitchen, burger was delicious. In the morning hiked the trail around the campground, very peaceful & quiet. Overall we had a memorable stay.

Reviewed on Oct 4, 2025

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

3 out of 5
Save 100% on your flight
Price was $3,324, price is now $2,551 per person
$2,551
per person
Dec 4 - Dec 7
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
No reviews
Deer Mountain Inn

Deer Mountain Inn

2 out of 5
Price was $1,311, price is now $1,033 per person
$1,033
per person
Dec 4 - Dec 7
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
9/10 Wonderful! (4 reviews)
I loved the guest room with the pool table and self attend bar.

Reviewed on Oct 22, 2024

Modern Catskills Escape w/ Open Living, Steam Shower, Fireplace & Hot Tub w/ Mountain Views, Minutes From Woodstock & Trails Suncliff Vista

Modern Catskills Escape w/ Open Living, Steam Shower, Fireplace & Hot Tub w/ Mountain Views, Minutes From Woodstock & Trails Suncliff Vista

3 out of 5
Price was $1,311, price is now $1,036 per person
$1,036
per person
Dec 4 - Dec 7
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
No reviews
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Price was $993, price is now $799 per person
$799
per person
Dec 4 - Dec 7
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
9.6/10 Exceptional! (180 reviews)
Great property, great location and great landscape but my room was over charged as it looked like a « small motel room ». When going to my room, I had to go through a balcony offering full view… on the room next door. I saw my neighbor, naked going out his shower. He was surprised as much as I was. I heard him having calls, as the wall separating the 2 rooms is super thin. Last but not least, the snobbery and arrogance of the two ladies at the front desk (check in and check out) is totally unnecessary considering the category of the hotel and the level of service (no breakfast).

Reviewed on Oct 9, 2025

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Bearsville Hotel Deals

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
$122 nightly
The price is $137 total per night from Oct 19 to Oct 20
$137 total
Oct 19 - Oct 20
Total with taxes and fees
7.6/10 Good! (1,013 reviews)
"I was pleasantly surprised with how gorgeous this hotel was. My room was super clean. The fitness area along with the pool were beautiful. If I'm ever in the area again this is where I will be staying!"

Reviewed on Oct 8, 2025

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
$146 nightly
The price is $157 total per night from Oct 20 to Oct 21
$157 total
Oct 20 - Oct 21
Total with taxes and fees
9.2/10 Wonderful! (778 reviews)
"The whole lodge is classy including the rooms. Beds were pretty soft however but only slept there one night so it was ok. Was pleasantly surprised they had free breakfast which was in a beautiful room with a lit fireplace. Breakfast was coffee, muffins, fresh fruit, and a variety of bagels. The bagels ..."

Reviewed on Oct 8, 2025

Hunter Lodge, a Bluebird by Lark
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $119 total per night from Nov 10 to Nov 11
$119 total
Nov 10 - Nov 11
Total with taxes and fees
9.2/10 Wonderful! (657 reviews)
"Great, clean hotel"

Reviewed on Oct 3, 2025

Hotel Vienna
See all 2,427 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.

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 $546 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.