Bearsville Vacations from $799

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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.
Hotel Vienna

Hotel Vienna

3 out of 5
Price was $967, price is now $799 per person
$799
per person
Sep 3 - Sep 7
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9.4/10 Exceptional! (810 reviews)
The access to the Windam Path was great. It is a lovely, easy walk by a stream and through meadows.

Reviewed on Jun 19, 2026

The Haüs Windham

The Haüs Windham

2 out of 5
Save 100% on your flight
Price was $1,391, price is now $1,061 per person
$1,061
per person
Sep 3 - Sep 7
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
7.6/10 Good! (29 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

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

3 out of 5
Save 100% on your flight
Price was $3,248, price is now $2,477 per person
$2,477
per person
Aug 7 - Aug 12
found 9 hours ago
Roundtrip flight included
Baltimore (BWI) to Hudson (HCC)
No reviews
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3 out of 5
Save 100% on your flight
Price was $4,333, price is now $3,564 per person
$3,564
per person
Sep 3 - Sep 7
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
No reviews
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,385, price is now $1,186 per person
$1,186
per person
Aug 7 - Aug 12
found 9 hours ago
Roundtrip flight included
Baltimore (BWI) to Hudson (HCC)
8.8/10 Excellent! (100 reviews)
Beautiful and spacious balcony overlooking the mountains and golf course. We loved the view from our room 521. . Great place to relax before dinner with a glass of wine/cheese. Location is good within walking distance to a most wonderful restaurant named prominence. Highly recommend. The on site restaurant was nice too. Biggest disadvantage was the tv as it does not have any cable and then ending up with no signal at all. Other than that it was a really great place to stay.

Reviewed on Jun 15, 2026

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Bearsville Hotel Deals

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
$154 nightly
The price is $166 total per night from Jul 12 to Jul 13
$166 total
Jul 12 - Jul 13
Total with taxes and fees
9.2/10 Wonderful! (980 reviews)
"Total surprise. Very nice"

Reviewed on Jun 24, 2026

Hunter Lodge, a Bluebird by Lark
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
$202 nightly
The price is $226 total per night from Jul 9 to Jul 10
$226 total
Jul 9 - Jul 10
Total with taxes and fees
9/10 Wonderful! (518 reviews)
"Wonderful and Cute"

Reviewed on Jun 26, 2026

AutoCamp Catskills
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$253 nightly
The price is $287 total per night from Jun 28 to Jun 29
$287 total
Jun 28 - Jun 29
Total with taxes and fees
8.2/10 Very Good! (905 reviews)
"We thought we were going to be on the historic hotel but instead placed at the conference center which is delemare inn. Didn’t realize there were two properties"

Reviewed on Jun 22, 2026

Beekman Arms and Delamater Inn
See all 2,506 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 $799 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.