Wolfeboro Vacations from $708

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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.
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Save 100% on your flight
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (71 reviews)
The location is perfect with the golf course right next door and sitting up on the hill overlooking the harbor. The restaurant serves wonderful meals, one of the best lobster bisque we’ve ever had. The wrap around porch is awesome with heaters. In saying all this, the inn needs some TLC. Our room had paint chipping on the walls and all around the shower. The shower head was awful. There isn’t a main door to the front desk and the one our driver brought us in was like we were walking into a shed, very weird . We will go back to the restaurant but we wouldn’t stay over.

Reviewed on Jun 20, 2025

The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 6
found 12 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9/10 Wonderful! (25 reviews)
Excellent and highly recommend!

Reviewed on Jun 27, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.2/10 Wonderful! (1,533 reviews)
The beds were super comfortable! The entire staff was helpful and kind.

Reviewed on Jul 6, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,003 reviews)
Everything about this location is five stars

Reviewed on Jul 6, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.6/10 Exceptional! (209 reviews)
Great place! Super convenient

Reviewed on Jul 4, 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

Lake Wentworth Inn
Lake Wentworth Inn
2 out of 5
427 Center St, Wolfeboro, NH
$179 nightly
The price is $194 total per night from Jul 9 to Jul 10
$194 total
Jul 9 - Jul 10
Total includes taxes and fees
9.2/10 Wonderful! (432 reviews)
"Property is a hidden gem! Staff, Terry and Tammy are rock stars! We will be back!"

Reviewed on Jul 6, 2025

Lake Wentworth Inn
The Wolfeboro Inn
The Wolfeboro Inn
3.5 out of 5
90 N Main St, Wolfeboro, NH
$258 nightly
The price is $280 total per night from Jul 9 to Jul 10
$280 total
Jul 9 - Jul 10
Total includes taxes and fees
8/10 Very Good! (513 reviews)
"Great location"

Reviewed on Jun 18, 2025

The Wolfeboro Inn
The Windrifter Resort
The Windrifter Resort
2.5 out of 5
337 South Main Street, Wolfeboro, NH
$175 nightly
The price is $190 total per night from Jul 15 to Jul 16
$190 total
Jul 15 - Jul 16
Total includes taxes and fees
8.8/10 Excellent! (309 reviews)
"The Staff was very friendly, the building and grounds were dated but in good condition. On papaer it looked the docks were on or near the main buildings but they were 1.5 miles away. the smoking area was between our room and the parking lot. So it seemed there was always someone sitting or standing ..."

Reviewed on Jun 30, 2025

The Windrifter Resort
See all 2,100 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 $708 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.