Wolfeboro Vacations from $380

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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.
Dormir

Dormir

3 out of 5
Save 100% on your flight
Price was $518, price is now $380 per person
$380
per person
Oct 14 - Oct 17
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.8/10 Excellent! (1,003 reviews)
For the price I would have liked to have my bed made and fresh towels replaced every day. Breakfast was really good but ditch those fake eggs. Over all it was great. Would stay there again.

Reviewed on Aug 17, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,741, price is now $1,147 per person
$1,147
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!

Reviewed on Aug 9, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Save 100% on your flight
Price was $803, price is now $555 per person
$555
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Lebanon (LEB)
9/10 Wonderful! (732 reviews)
Remote location. Facilities were a good value.

Reviewed on Aug 16, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $760, price is now $526 per person
$526
per person
Oct 27 - Oct 30
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
I had a wonderful stay! The place was clean, cozy, and exactly as described. The location was perfect, which made everything smooth and easy. I’d happily stay here again and recommend it to anyone visiting Portland.

Reviewed on Aug 22, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $987, price is now $744 per person
$744
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.8/10 Exceptional! (68 reviews)
nice building walkable to shopping + dining

Reviewed on Aug 22, 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
$175 nightly
The price is $190 total per night from Sep 24 to Sep 25
$190 total
Sep 24 - Sep 25
Total with taxes and fees
9.4/10 Exceptional! (464 reviews)
"Amazing place to stay!"

Reviewed on Aug 18, 2025

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
$224 nightly
The price is $243 total per night from Sep 21 to Sep 22
$243 total
Sep 21 - Sep 22
Total with taxes and fees
8/10 Very Good! (523 reviews)
"Peace and tranquillity calmness , too bad everything shuts down early in Wolfeboro."

Reviewed on Aug 12, 2025

The Wolfeboro 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 Sep 7 to Sep 8
$136 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (318 reviews)
"Awesome"

Reviewed on Jul 30, 2025

The Windrifter Resort
See all 2,069 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.

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 $380 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.