Wolfeboro Vacation Packages

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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.

Top Wolfeboro Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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
per person
Aug 21 - Aug 25
found 2 hours ago
Roundtrip flight included
Halifax (YHZ) to Portland (PWM)
9.2/10 Wonderful! (1,533 reviews)
Lovely hotel in a perfect location - some elements of the room hadn’t been cleaned that well but made up for by the complimentary coffee and cookie station.

Reviewed on Jul. 3, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (209 reviews)
Great place! Super convenient

Reviewed on Jul. 4, 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
Aug 21 - Aug 25
found 2 hours ago
Roundtrip flight included
Halifax (YHZ) to Portland (PWM)
9.4/10 Exceptional! (1,318 reviews)
Absolutely lovely and convenient hotel. Only complaint was about the air conditioning. Even though it wasn’t that hot a night (in the 60s) and day (80). The cooling struggled to keep up. We wanted the temperature to be 68 but we couldn’t get it cooler than 73.

Reviewed on Jul. 5, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
per person
Aug 21 - Aug 25
found 2 hours ago
Roundtrip flight included
Halifax (YHZ) to Portland (PWM)
9.6/10 Exceptional! (147 reviews)
Everything was wonderful, we highly recommend staying here to anyone considering it.

Reviewed on Jun. 13, 2025

Ready to book your vacation to Wolfeboro?

 

Choose your dates

Wolfeboro Hotel Deals

Lake Wentworth Inn
Lake Wentworth Inn
2 out of 5
427 Center St, Wolfeboro, NH
The price is CA $219 per night from Jul 7 to Jul 8
CA $219
CA $238 total
Jul 7 - Jul 8
includes taxes & fees
9.2/10 Wonderful! (430 reviews)
"I arrived late and they sent me a text about how to access my room. They are dog friendly. I left early and I got a quick cup of coffee and left a note at desk. No muss, no fuss!"

Reviewed on Jul. 1, 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
The price is CA $269 per night from Jul 8 to Jul 9
CA $269
CA $336 total
Jul 8 - Jul 9
includes taxes & 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
The price is CA $214 per night from Jul 7 to Jul 8
CA $214
CA $232 total
Jul 7 - Jul 8
includes taxes & fees
8.8/10 Excellent! (308 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Wolfeboro

Allen Albee Beach

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

Frequently asked questions

How much does a Wolfeboro vacation package cost?
You'll find cheap prices from CA $1,093 on Expedia for your Wolfeboro escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Wolfeboro costs.
What are the cheapest months to go to Wolfeboro?
You can generally find lower prices and better availability in January, March and December. Take a look at our cheap Wolfeboro vacation packages and you could get some great off-season discounts.
How many days is enough for Wolfeboro?
Generally, a handful of days is enough to explore the main attractions during your Wolfeboro vacation. However, if you'd like to have more time to unwind or go on day trips, consider extending your itinerary.
Is it worth booking a vacation package to Wolfeboro?
From leading attractions such as Kingswood Golf Club and Allen Albee Beach to its excellent family-friendly attractions, a Wolfeboro vacation is sure to exceed your expectations. With so much to do and see, it's time to find out for yourself why Wolfeboro is such a good vacation destination.
How to find the best Wolfeboro package deals?
Begin your search for a Wolfeboro package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Wolfeboro package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Wolfeboro escape underway.
Is it cheaper to book a Wolfeboro vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Wolfeboro vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Wolfeboro?
If you're planning a spontaneous Wolfeboro trip, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Wolfeboro?

  1. Pick your dates: What you plan to do in Wolfeboro and your preferred season will help you decide when to get away.
  2. Set a budget: Consider costs such as flights, food and transportation when working out how much to set aside for your trip to Wolfeboro. Then, select a hotel that works with your budget, whether that's a low-cost option or a high-end getaway.
  3. Decide how long to go away for: Now that you're up to speed on Wolfeboro, you can figure out the perfect length of your vacation. Create a draft itinerary and allocate enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Wolfeboro vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.