Wolfeboro Vacations from $348

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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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $541, price is now $348 per person
$348
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Perfect hotel for a stay in Portland ! We will definitely be back. Appreciate Kristen for her generosity in morning with resolution to coffee .

Reviewed on Nov 4, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,447, price is now $897 per person
$897
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.4/10 Exceptional! (1,016 reviews)
Crew members were amazing! Views could not be beat!

Reviewed on Nov 2, 2025

The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Save 100% on your flight
Price was $785, price is now $533 per person
$533
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
No reviews
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $758, price is now $583 per person
$583
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (283 reviews)
Absolutely wonderful experience. We are traveling with our small dog Buttons. The staff all made her feel so welcomed. We were able to eat in the bar area with her and she had her own menu to choose from. The property and grounds are well maintained. The view is stunning. Would absolutely recommend! Hope to stay again

Reviewed on Oct 31, 2025

Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
Downtown Portland
Price was $568, price is now $439 per person
$439
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,016 reviews)
The room was clean and very basic. The staff was excellent. The view was okay, but I probably shouldn’t have gotten the water view.

Reviewed on Nov 3, 2025

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Discover the most popular places to visit in Wolfeboro

Allen Albee Beach

4/5(1 review)

If a restful vacation is part of your travel plans, Allen Albee Beach might be the perfect place to seek out during your trip to Wolfeboro. Stroll along the area's lakeside or simply enjoy its bars.

Allen Albee Beach

Brewster Beach

Why not spend a carefree afternoon at Brewster Beach during your travels in Wolfeboro? Stroll along the area's lakeside or simply enjoy its bars.

Brewster Beach

Kingswood Golf Club

3/5(1 review)

Enjoy a round of golf in Wolfeboro at Kingswood Golf Club. Stroll along the lakeside or seek out the ski slopes.

Kingswood Golf Club

Wolfeboro Hotel Deals

The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
90 N Main St, Wolfeboro, NH
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $179 total per night from Nov 6 to Nov 7
$179 total
Nov 6 - Nov 7
Total with taxes and fees
8/10 Very Good! (543 reviews)
Hotel is located in a great spot, easy to walk to town. Room was nice and clean. It looked like the property needed overall maintenance. Lots of flaking paint and wood rot.

Reviewed on Oct 22, 2025

The Wolfeboro Inn
Lake Wentworth Inn

Lake Wentworth Inn

2 out of 5
427 Center St, Wolfeboro, NH
$120 nightly
The price is $131 total per night from Nov 5 to Nov 6
$131 total
Nov 5 - Nov 6
Total with taxes and fees
9.4/10 Exceptional! (508 reviews)
Staff was WONDERFUL. Glad to see upgrades to this motel. But the bed was tight and quite uncomfortable (time for an upgrade there!) It is lovely for a low budget, clean option. Its near other restaurants. It has some nice family friendly amenities.

Reviewed on Nov 2, 2025

Lake Wentworth 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 Nov 5 to Nov 6
$136 total
Nov 5 - Nov 6
Total with taxes and fees
8.6/10 Excellent! (353 reviews)
Room was clean and comfortable close to the area we needed to visit

Reviewed on Oct 25, 2025

The Windrifter Resort
See all 2,066 properties in Wolfeboro
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 $348 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.