Wolfeboro Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Wolfeboro

Lake Wentworth Inn

Lake Wentworth Inn

2 out of 5
427 Center St, Wolfeboro, NH
The price is S$224 per night from 28 Jul to 29 Jul
S$224
28 Jul - 29 Jul
includes taxes & fees
9.4/10 Exceptional! (436 reviews)
"Excellent property, clean, well maintained, great pool, short walk to the lake, adorable greeter, plenty of space for activities, grilling, and kids to play, short drive to Wolfeboro town center. We are hoping to make it annual."

Reviewed on 8 Jul, 2025

Lake Wentworth Inn
The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
90 N Main St, Wolfeboro, NH
The price is S$403 per night from 20 Jul to 21 Jul
S$403
20 Jul - 21 Jul
includes taxes & fees
8/10 Very Good! (513 reviews)
"Great location"

Reviewed on 18 Jun, 2025

The Wolfeboro Inn
The Windrifter Resort

The Windrifter Resort

2.5 out of 5
337 South Main Street, Wolfeboro, NH
The price is S$219 per night from 17 Jul to 18 Jul
S$219
17 Jul - 18 Jul
includes taxes & fees
8.8/10 Excellent! (310 reviews)
"I loved the different building and that they all had balconies. We were there for a wedding in town and our family had different units. Understand the indoor pool, but I prefer the outdoors when swimming. Kids loved the pool though. Too nice to be indoors when we were there."

Reviewed on 8 Jul, 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.

Frequently asked questions

How much does a Wolfeboro holiday package cost?
You can grab a holiday package to this popular destination on Expedia. But how much your holiday 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'd like to book a cheap Wolfeboro holiday package, consider travelling in January, March and December. You'll usually find better prices on accommodation and flights during these months --- perfect for budget-conscious travellers.
How many days is enough for Wolfeboro?
With a well-organised travel plan, you can easily visit the top Wolfeboro sights in a few days. But if you'd like to discover hidden spots or go on day trips, consider booking your Wolfeboro holiday for longer.
Is it worth booking a holiday package to Wolfeboro?
Known for its family-friendly attractions and home to leading attractions like Kingswood Golf Club, a Wolfeboro holiday is bound to impress. Another highlight to check out? Don't miss Allen Albee Beach.
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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Wolfeboro holiday as a package?
Expedia holiday 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 holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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.
How to plan a trip to Wolfeboro?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favourite time of year and the activities available will also help you decide when to holiday in Wolfeboro.
  2. Budget wisely: In addition to the price of your stay, you'll need to factor in other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that could arise during your trip to Wolfeboro.
  3. Decide how long to go for: Now that you're more familiar with Wolfeboro, you can work out the right length of your break. Pull together a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customised Wolfeboro holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.