Wolfeboro Vacations from $597

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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.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $930, price is now $597 per person
$597
per person
Oct 19 - Oct 24
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $2,612, price is now $1,759 per person
$1,759
per person
Oct 19 - Oct 24
found 7 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (188 reviews)
This hotel is amazing. The rooms, beds, and all the details are so incredible. I wish I could have stayed longer. Check in was a breeze as well. You can tell they take a lot of care and thought into the property. I will definitely be back

Reviewed on Jul 25, 2026

AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Save 100% on your flight
Price was $1,689, price is now $1,229 per person
$1,229
per person
Oct 1 - Oct 6
found 7 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (250 reviews)
Wonderful historic property updated with in-house suites & cabin-style lodgings. Adequate parking. Room was comfortable, new bathrooms & nice breakfast area. The breakfast itself was TDF!! The neighborhood is authentic. Walkable to downtown. Highly recommend.

Reviewed on Jul 20, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,273, price is now $1,654 per person
$1,654
per person
Sep 16 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (358 reviews)
Docent is a low touch hotel that has very clean, great spaces. The staff is incredible and helpful.

Reviewed on Jul 27, 2026

Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
Save 100% on your flight
Price was $1,032, price is now $759 per person
$759
per person
Sep 16 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
7.8/10 Good! (1,012 reviews)

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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.
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Wolfeboro Hotel Deals

Lake Wentworth Inn

Lake Wentworth Inn

2 out of 5
427 Center St Wolfeboro NH
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $190 total per night from Jul 28 to Jul 29
$190 total
Jul 28 - Jul 29
Total with taxes and fees
9.4/10 Exceptional! (568 reviews)
"Excellent value for the money. Clean and newly renovated. Front desk was friendly and helpful to us. The location was close to center of town and lake. Would definitely return again."

Reviewed on Jul 27, 2026

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
$252 nightly
The price is $274 total per night from Aug 25 to Aug 26
$274 total
Aug 25 - Aug 26
Total with taxes and fees
8.2/10 Very Good! (616 reviews)
"Coffee and pastries in the lobby were a great touch."

Reviewed on Jul 27, 2026

The Wolfeboro Inn
The Windrifter Resort

The Windrifter Resort

2.5 out of 5
337 South Main Street Wolfeboro NH
$165 nightly
The price is $179 total per night from Aug 13 to Aug 14
$179 total
Aug 13 - Aug 14
Total with taxes and fees
8.8/10 Excellent! (409 reviews)
"The front desk clerk Adrian, was very helpful with the questions I had and gave great advice. The apartment was nice and was very comfortable for are stay."

Reviewed on Jul 20, 2026

The Windrifter Resort
See all 2,201 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 $597 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.