Wolfeboro Vacations from $380

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Your Wolfeboro Vacation

Prepare to experience Wolfeboro on your terms with a custom Wolfeboro vacation package! Uncovering the charms of this fascinating city is made easier with a base in a neighborhood such as Pine River Pond, which is good for fishing, among plenty of other things. Lake Wentworth, Allen Albee Beach and Kingswood Golf Club are just some of the many attractions you'll want to check out during your trip to Wolfeboro. Check out Expedia's wide range of travel options and start organizing your dream vacation to Wolfeboro now.

The Latest Wolfeboro vacation packages

Price found within the past 48 hours. Click for updated prices.
Dormir
Cliff House Maine
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Docent's Collection
The Weldon Hotel
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Discover the most popular places to visit in Wolfeboro

Wolfeboro Hotel Deals

Lake Wentworth Inn

Lake Wentworth Inn

2 out of 5
427 Center St, Wolfeboro, NH
$175 nightly
The price is $190 total per night from Sep 24 to Sep 25
$190 total
Sep 24 - Sep 25
Total with taxes and fees
9.4/10 Exceptional! (464 reviews)
"Amazing place to stay!"

Reviewed on Aug 18, 2025

Lake Wentworth Inn
The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
90 N Main St, Wolfeboro, NH
Fully refundableReserve now, pay when you stay
$224 nightly
The price is $243 total per night from Sep 21 to Sep 22
$243 total
Sep 21 - Sep 22
Total with taxes and fees
8/10 Very Good! (523 reviews)
"Peace and tranquillity calmness , too bad everything shuts down early in Wolfeboro."

Reviewed on Aug 12, 2025

The Wolfeboro Inn
The Windrifter Resort

The Windrifter Resort

2.5 out of 5
337 South Main Street, Wolfeboro, NH
$125 nightly
The price is $136 total per night from Sep 7 to Sep 8
$136 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (318 reviews)
"Awesome"

Reviewed on Jul 30, 2025

The Windrifter Resort
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.

Wolfeboro Ski Vacation Packages

Do it your way with one of our Wolfeboro ski vacation packages. Whether you're looking for an adrenaline-fueled adventure, some respite at altitude or even both, your perfect getaway begins with Expedia. Make the trip to Wolfeboro from December to March and you'll find around 7 runs operating at this top winter destination in United States of America. Try your hand at tree, mogul and downhill skiing or hone your technique in a beginner-friendly area. You can rent the equipment you need from the ski village. There's also a spa and wellness center to take advantage of here. After a fun day of slopeside activities, your tired legs will appreciate a bit of pampering. If you're organizing a family ski vacation in Wolfeboro, the kids can look forward to snowshoeing, night skiing and ice skating.

How To Get Around

Many ski enthusiasts who book one of our Wolfeboro vacation packages jet into Portsmouth International Airport. From there, it's one hour before you're slaloming down the slopes of Wolfeboro's most thrilling runs. It takes 10 minutes to get to the runs from the middle of Wolfeboro, and free parking is available. If you're driving during the winter months, tire chains are recommended. Save big on your ski vacation when you book everything together. Select from a season-pass ticket or a full-day ticket, then combine your flights, hotel and a car rental into a package to get the cheapest price possible. Take a look at our Wolfeboro ski package deals for some ideas.

Wolfeboro Resort Ski Info

Cost of 1-day lift pass
Under $25
Easy runs
2
Moderate runs
1
Advanced runs
4

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Frequently asked questions

How much does a Wolfeboro vacation package cost?
You can grab a vacation package to this popular destination from $380 on Expedia. But how much your vacation to Wolfeboro costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Wolfeboro?
If you're hoping to score a cheap Wolfeboro vacation package, consider planning a trip in May, August and December. You'll usually find better prices on flights and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Wolfeboro?
Usually, a handful of days is enough to go to the top sights during your Wolfeboro vacation. However, if you'd like to have time to unwind or go on day trips, consider extending your itinerary.
Is it worth booking a vacation package to Wolfeboro?
Boasting a host of highlights starting with its top-notch family-friendly attractions, Wolfeboro is a good vacation destination. Whether you'd like to discover attractions like Kingswood Golf Club and Allen Albee Beach or take the road less traveled, you'll have plenty to keep you busy during your Wolfeboro vacation.
How to find the best Wolfeboro package deals?
Bagging a cheap Wolfeboro package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Wolfeboro 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 Wolfeboro vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component individually. And you'll still get the freedom to create a tailored Wolfeboro vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Wolfeboro?
If you're considering a spur-of-the-moment Wolfeboro getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Wolfeboro vacation packages?
If you're like us, you love traveling but are not a fan of the big 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 overall cost of your Wolfeboro trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.