Wolfeboro Vacations from $658
Book a Hotel + Flight or Car together to unlock savings
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.
The Meadowmere Resort
$658
per person
Nov 19 - Nov 23
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
8.6/10 Excellent! (1,008 reviews)
Great mid-price range option! Still walking distance to most things you’ll want to do in ogunquit and they let you check in early just to park even if your room isn’t ready yet, which is valuable in of itself. The outdoor horrible was very spacious and the up keep of the entire property was very nice. Free continental breakfast too
Reviewed on Oct 11, 2026
84 Main
$716
per person
Nov 20 - Nov 24
found 19 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (58 reviews)
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.
Reviewed on Jul 17, 2026
Cliff House Maine
Bald Head
$1,590
per person
Dec 26 - Dec 29
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Younger Families beware , you will not be able to enjoy the Main pool with kids under 13.
Reviewed on Oct 15, 2026
Nautical Mile
$930
per person
Nov 27 - Dec 1
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Portland (PWM)
8.6/10 Excellent! (25 reviews)
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.
Reviewed on Sep 8, 2026
Stay near popular Wolfeboro attractions
Lake Wentworth
9.6/10 (34 reviews)
Lake Wentworth offers pristine waters and tranquility across its 3,100 acres, a serene alternative to busy Lake Winnipesaukee. Paddle through clear waters while spotting local wildlife or enjoy its picturesque shores.
Wolfeboro Abenaki Ski Area
8.0/10 (1 review)
America's oldest small ski area offers seven trails and night skiing in a welcoming community setting. Enjoy uninterrupted runs with no lift lines and warm up in the cozy lodge with its crackling wood stove.
Libby Museum
10.0/10 (1 review)
You can spend an afternoon studying the exhibits at Libby Museum during your trip to Wolfeboro. Stroll along the beautiful beaches in this relaxing area, or check out its lively bars.
Allen Albee Beach
9.2/10 (20 reviews)
This peaceful lakeside retreat offers pristine sandy shores and mountain views on Lake Wentworth. Enjoy the quiet morning hours with a picnic at one of the shaded tables equipped with grills.
Clark House Museum
You can spend an afternoon exploring the galleries in Clark House Museum in Wolfeboro. Wander the lakeside and beautiful beaches in this relaxing area.
Brewster Beach
9.6/10 (8 reviews)
This tranquil public beach offers pristine sandy shores and crystal-clear waters of Lake Winnipesaukee. Enjoy a peaceful day swimming and picnicking with panoramic lake views in charming Wolfeboro.
Wright Museum
9.2/10 (7 reviews)
The Wright Museum offers an immersive journey through America's WWII home front with authentic period settings. Explore the Time Tunnel's 1940s living spaces and see military vehicles in the Military Gallery.
Carry Beach
Carry Beach offers shallow, sandy-bottomed waters perfect for families with young children on Lake Winnipesaukee. Enjoy the tranquil shoreline with shaded picnic areas and spectacular lake sunsets during summer months.
Wolfeboro Hotel Deals
Lake Wentworth Inn
427 Center St Wolfeboro NH
Fully refundableReserve now, pay when you stay
$120 nightly
$130 total
Oct 18 - Oct 19
Total with taxes and fees
9.4/10 Exceptional! (645 reviews)
"Great stay!"
Reviewed on Oct 13, 2026
The Windrifter Resort
337 South Main Street Wolfeboro NH
$135 nightly
$146 total
Oct 19 - Oct 20
Total with taxes and fees
The Wolfeboro Inn
90 N Main St Wolfeboro NH
Fully refundableReserve now, pay when you stay
$218 nightly
$237 total
Nov 1 - Nov 2
Total with taxes and fees
8.2/10 Very Good! (655 reviews)
"Not sure what the amenities fee is for. Who’s using the lake access this time of the year? $25 for the burnt AM coffee and cookies? For the price, the room should be nicer, cleaner. Our room was almost in the basement. The window opened to earth/bushes in the parking lot. Parking was fine, location ..."
Reviewed on Oct 11, 2026
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 Wolfeboro Vacation Packages
Wolfeboro Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 2,800 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Allen Albee Beach, Brewster Beach and Wolfeboro Abenaki Ski Area |
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 $658 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.
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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.