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.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was CA $1,510, price is now CA $1,167 per person
CA $1,167
per person
Oct 1 - Oct 4
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (198 reviews)
The manager and the staff were amazing - we had an issue with the air conditioning in our room and they were very helpful and got us moved to another room. I wish there were some more options for food, and was disappointed that the bar was not staffed, but the inn was beautiful and the atmosphere relaxing!

Reviewed on Jul 4, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $2,169, price is now CA $1,497 per person
CA $1,497
per person
Aug 6 - Aug 9
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Had to wait 45 mins to get our room after arriving at 4:00…check in time. Not impressed with that and ours was not the only one not ready. Obviously, they have a staffing problem or so t know how to schedule. Also had three people at the front desk but only one seemed to be able to check in people at a time. Room was clean but the bathroom was so small it was hard to move around. Rooms were not sound proud either so we could constantly hear kids running up and down the halls. Overall the place was okay but wouldn’t go back again.

Reviewed on Jul 2, 2026

Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Price was CA $2,005, price is now CA $1,468 per person
CA $1,468
per person
Aug 10 - Aug 14
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.8/10 Excellent! (78 reviews)
An absolutely beautiful property and staff were incredibly kind and helpful! We had a late arrival and the two young gentlemen were waiting at the dock and they helped my sister and I with all our bags. The entire property was very clean and there were incredible views of the water and golf course. Looking forward to returning!

Reviewed on Jun 27, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $3,516, price is now CA $2,678 per person
CA $2,678
per person
Aug 10 - Aug 14
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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

Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Price was CA $1,669, price is now CA $1,274 per person
CA $1,274
per person
Aug 30 - Sep 3
found 11 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (351 reviews)
I was pleasantly surprised on the room, staff, inn and amenities. Beautiful grounds, wonderful restaurant and very comfortable room. I cannot recommend this property highly enough. Amazing stay!

Reviewed on Jul 6, 2026

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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
The price is CA $311 per night from Jul 12 to Jul 13
CA $311
CA $376 total
Jul 12 - Jul 13
includes taxes & fees
8.2/10 Very good! (599 reviews)
"Loved the waterfront view of the fireworks and curbside access to the parade on July 4th"

Reviewed on Jul 5, 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
The price is CA $242 per night from Jul 13 to Jul 14
CA $242
CA $262 total
Jul 13 - Jul 14
includes taxes & fees
9.4/10 Exceptional! (542 reviews)
"Nice staff, very helpful. Great A/C!"

Reviewed on Jul 5, 2026

Lake Wentworth Inn
The Windrifter Resort

The Windrifter Resort

2.5 out of 5
337 South Main Street Wolfeboro NH
The price is CA $236 per night from Jul 20 to Jul 21
CA $236
CA $257 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (405 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 2,199 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.
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Stay near popular Wolfeboro attractions

Lake Wentworth

9.6/10 (34 reviews)
Commune with nature and explore the great outdoors at Lake Wentworth during your travels in Wolfeboro. Stroll along the area's lakeside or simply enjoy its bars.
See properties

Frequently asked questions

How much does a Wolfeboro vacation package cost?
You'll find cheap prices from CA $1,167 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.

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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.