Willsboro Vacations from $503

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Your Willsboro Vacation

Let our vacation packages to Willsboro inspire your next great escape. There's loads to like about this lively city, starting with the neighborhood of South End, which is good for bars and pubs and dining. There's lots to do and see during a trip to Willsboro, including 1812 Homestead Museum and Oldham Theater. Browse Expedia's wide range of travel options and book your ideal vacation to Willsboro now.

The Latest Willsboro vacation packages

Price found within the past 48 hours. Click for updated prices.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $644, price is now $503 per person
$503
per person
Nov 27 - Nov 30
found 19 hours ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
9/10 Wonderful! (1,004 reviews)
We came to hotel after complicated driving for 7 hours tired and were met by friendly staff. Check in was fast and easy. After all we got excellent warm chocolate cookies. Love the hotel !!

Reviewed on Sep 13, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,083, price is now $705 per person
$705
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9/10 Wonderful! (2 reviews)
Gorgeous thoughtfully designed cabins with so many amenities/activities. Cliff house restaurant was delicious. Perfect getaway.

Reviewed on Sep 8, 2025

Gedney Farm

Gedney Farm

3.5 out of 5
Price was $824, price is now $601 per person
$601
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.2/10 Wonderful! (129 reviews)
Gedney Farms is very quiet, peaceful and rustic. Your stay is in a converted barn with towering ceilings, hard wood floors, and rustic reused furniture with no TV phones or radios. Note some rooms require stair climbing on winding stairs with sections without rails or handholds. Some bathtubs are very high. It would be helpful to talk to the location about the room accommodations if mobility is an issue. The staff is very unobtrusive almost to the point of non existent. The breakfast was fresh and healthy with plain Greek yogurt, granola, fresh fruits, hard boiled eggs, muffins and bread to toast. The grounds are well tended but not fussy and offer beauty, peace and quiet. The location is an easy 30 minutes to Tanglewood and 15 minutes to Stockbridge. It is nearby Berkshire Botanical Gardens, Dr. Suess Museum, WEB DuBois statue and homestead, Norman Rockwell museum, Monument mountain, Housatonic river and many art stores, general stores, outdoor activities. This area is car dependent.

Reviewed on Aug 12, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $979, price is now $727 per person
$727
per person
Oct 19 - Oct 24
found 9 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
7.4/10 Good! (522 reviews)
Beautiful hotel. So much history. Large pool and hot tub, with spa. Selection of restaurants at the hotel

Reviewed on Sep 12, 2025

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
Price was $686, price is now $537 per person
$537
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.6/10 Exceptional! (29 reviews)
Beautiful and very comfortable house. Our hosts were always friendly and accessible, breakfast was delicious!

Reviewed on Aug 30, 2025

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Discover the most popular places to visit in Willsboro

1812 Homestead Museum

You can spend an afternoon browsing the exhibits at 1812 Homestead Museum during your travels in Willsboro. While in this family-friendly area, you can savor the top-notch restaurants.

1812 Homestead Museum

Willsboro Hotel Deals

DoubleTree by Hilton Burlington Vermont

DoubleTree by Hilton Burlington Vermont

4 out of 5
870 Williston Rd, South Burlington, VT
Fully refundableReserve now, pay when you stay
$176 nightly
The price is $193 total per night from Sep 21 to Sep 22
$193 total
Sep 21 - Sep 22
Total with taxes and fees
DoubleTree by Hilton Burlington Vermont
Green Mountain Suites Hotel

Green Mountain Suites Hotel

3 out of 5
401 Dorset St, South Burlington, VT
Fully refundableReserve now, pay when you stay
$228 nightly
The price is $251 total per night from Sep 15 to Sep 16
$251 total
Sep 15 - Sep 16
Total with taxes and fees
Green Mountain Suites Hotel
Anchorage Inn

Anchorage Inn

3 out of 5
108 Dorset St, South Burlington, VT
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $111 total per night from Sep 15 to Sep 16
$111 total
Sep 15 - Sep 16
Total with taxes and fees
Anchorage Inn
See all 1,055 properties in Willsboro
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.

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Frequently asked questions

How much does a Willsboro vacation package cost?
You'll find cheap prices from $503 on Expedia for your Willsboro break. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Willsboro costs.
What are the cheapest months to go to Willsboro?
March, October and December are great times to search for cheap Willsboro vacation packages. Traveling in quieter periods means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Willsboro?
The ideal length of your Willsboro vacation depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to go to all the leading sights and discover some hidden spots along the way.
How to find the best Willsboro package deals?
Landing a cheap Willsboro package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Willsboro package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Willsboro vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging accommodations and flights individually. Better still, you can personalize your Willsboro escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Willsboro?
If you're considering an impromptu Willsboro trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Willsboro vacation packages?
Your Willsboro getaway is meant to be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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