Wolfeboro Vacations from $899

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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 $1,430, price is now $899 per person
$899
per person
Aug 20 - Aug 24
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
Clean rooms and surroundings…helpful staff

Reviewed on Jun 28, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,593, price is now $1,035 per person
$1,035
per person
Aug 20 - Aug 24
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.6/10 Excellent! (1,003 reviews)
Price was good for the amenities offered and location. Our room was just recently renovated.

Reviewed on Jun 22, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $2,403, price is now $1,656 per person
$1,656
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (185 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.

Reviewed on Jun 26, 2026

Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was $1,545, price is now $1,068 per person
$1,068
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.8/10 Excellent! (196 reviews)
We had a really wonderful visit at the Inn at Diamond Cove. It was a special adventure and the staff tried to work with us to help us enjoy our visit after arriving very late at night for a one night /one day stay. We knew nothing about the inn or the island's history so it was a leap of faith and well worth it.

Reviewed on Jun 29, 2026

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $1,950, price is now $1,457 per person
$1,457
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (123 reviews)
Beautiful place to stay in the middle of a quiet street and walking distance to many spots. The rooms and common areas were clean and beautifully maintained. Staff was ready to answer any questions you had via phone or text. I loved this inn and would choose it again. Definitely recommend it !

Reviewed on Jun 6, 2026

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Stay near popular Wolfeboro attractions

Lake Wentworth

9.6/5 (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

The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
90 N Main St Wolfeboro NH
Fully refundableReserve now, pay when you stay
$244 nightly
The price is $264 total per night from Jun 30 to Jul 1
$264 total
Jun 30 - Jul 1
Total with taxes and fees
8.2/10 Very Good! (593 reviews)
"The room was beautiful and the location close to downtown Wolfeboro was perfect. The Tavern was fine for a snack but dinner in the offered more variety. Great weekend."

Reviewed on Jun 27, 2026

The Wolfeboro Inn
Lake Wentworth Inn

Lake Wentworth Inn

2 out of 5
427 Center St Wolfeboro NH
Fully refundableReserve now, pay when you stay
$172 nightly
The price is $187 total per night from Jun 30 to Jul 1
$187 total
Jun 30 - Jul 1
Total with taxes and fees
9.4/10 Exceptional! (541 reviews)
"Amazing people that help us so much with the staying at the hotel"

Reviewed on Jun 29, 2026

Lake Wentworth Inn
The Windrifter Resort

The Windrifter Resort

2.5 out of 5
337 South Main Street Wolfeboro NH
$185 nightly
The price is $201 total per night from Jun 30 to Jul 1
$201 total
Jun 30 - Jul 1
Total with taxes and fees
8.8/10 Excellent! (404 reviews)
"The shower and bathroom were not cleaned prior to our arrival. The staff took care of it after I called and let them know unfortunately after I was in the shower. Housekeeping came right away to clean the whole room."

Reviewed on Jun 29, 2026

The Windrifter Resort
See all 2,196 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 $899 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.