Willow Vacations from $635

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Your Willow Vacation

When a city break is calling, answer it with a Willow vacation package. The neighborhood of West Hurley, which is great for cycling, hiking and walking, makes a great base for your adventures. Fill your itinerary with visits to Overlook Mountain Trailhead, Woodstock Music Shop and Karma Triyana Dharmachakra Monastery, some of the things you should see during a trip to Willow. Your dream Willow vacation is clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored just for you.

The Latest Willow vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Vienna

Hotel Vienna

3 out of 5
Price was $863, price is now $635 per person
$635
per person
Sep 10 - Sep 15
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Hudson (HCC)
9.4/10 Exceptional! (825 reviews)

The Haüs Windham

The Haüs Windham

2 out of 5
Save 100% on your flight
Price was $1,199, price is now $869 per person
$869
per person
Sep 10 - Sep 15
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Hudson (HCC)
8/10 Very Good! (32 reviews)
Abia mucho ruido en la noche I abian muchas moscas y solo abia 1 cobija y eramos tres

Reviewed on Jul 25, 2026

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $7,515, price is now $5,766 per person
$5,766
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
No reviews

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $7,527, price is now $5,779 per person
$5,779
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
No reviews

Eastwind Windham

Eastwind Windham

3.5 out of 5
Price was $1,147, price is now $904 per person
$904
per person
Sep 10 - Sep 15
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Hudson (HCC)
9.2/10 Wonderful! (110 reviews)

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Stay near popular Willow attractions

James Cox Gallery

You can spend time browsing the exhibits at James Cox Gallery during your trip to Willow. Amble around this relaxing area's forest, or seek out the ski slopes.
See properties

Willow Hotel Deals

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
$139 nightly
The price is $157 total per night from Jul 30 to Jul 31
$157 total
Jul 30 - Jul 31
Total with taxes and fees
8.2/10 Very Good! (938 reviews)
"The room had a bad smell of"

Reviewed on Jul 26, 2026

Beekman Arms and Delamater Inn
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
$141 nightly
The price is $152 total per night from Aug 10 to Aug 11
$152 total
Aug 10 - Aug 11
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
$209 nightly
The price is $226 total per night from Aug 26 to Aug 27
$226 total
Aug 26 - Aug 27
Total with taxes and fees
9.6/10 Exceptional! (261 reviews)
"It was great!"

Reviewed on Jul 26, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
See all 2,272 properties in Willow
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 Willow Vacation Packages

Willow Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Mount Tremper Arts, James Cox Gallery and Catskill Mountains

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Frequently asked questions

How much does a Willow vacation package cost?
You'll find cheap prices from $635 on Expedia for your Willow break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Willow costs.
What are the cheapest months to go to Willow?
You can typically find reduced prices and better availability in November, December and January. Browse our cheap Willow vacation packages and you could get some great off-season deals.
How many days is enough for Willow?
The ideal length for your Willow vacation depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to check out all the main attractions and discover some hidden treasures along the way.
How to find the best Willow package deals?
Bagging a cheap Willow package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Willow package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Willow vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking hotels and flights individually. Better still, you can personalize your Willow getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Willow?
If you're planning a spur-of-the-moment Willow adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Willow vacation packages?
If you're like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Willow trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.