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.
Portland Harbor Hotel
Downtown Portland
Price was CA $1,882, price is now CA $1,369 per person
CA $1,369
per person
May 16 - May 21
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.
Reviewed on Mar 24, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $2,255, price is now CA $1,782 per person
CA $1,782
per person
May 16 - May 21
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!
Reviewed on Mar 10, 2026
Portland Regency Hotel & Spa
Downtown Portland
Price was CA $1,717, price is now CA $1,372 per person
CA $1,372
per person
May 16 - May 21
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,599 reviews)
Our stay at Portland Regency Hotel and Spa was amazing. The staff greeted us with such warmth. Our room was exceptional and the food was superb.
Reviewed on Mar 22, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $2,038, price is now CA $1,629 per person
CA $1,629
per person
May 16 - May 21
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
Property is in an excellent location with so much to see and do (and eat) in walking distance. My room was clean, quiet, and well maintained. Staff interaction was minimal (by design) but the few times I spoke with the concierge on site she was pleasant and accommodating. My only negative comment is regarding the toiletry products. I’m a toilet paper snob and that angel soft just doesn’t cut it. Overall I am beyond satisfied with my stay and would absolutely stay here again.
Reviewed on Mar 22, 2026
The Weldon Hotel
Downtown Portland
Price was CA $2,170, price is now CA $1,788 per person
CA $1,788
per person
May 16 - May 21
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (94 reviews)
The hotel is in an ideal location in downtown Portland. The staff is so kind and very accommodating! The stay was beyond comfortable and is the place we will stay every time we return to Portland!
Reviewed on Mar 23, 2026
Wolfeboro Hotel Deals
The Wolfeboro Inn
90 N Main St Wolfeboro NH
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (561 reviews)
Stayed on 4 separate instances while renovating a house in Wolfeboro. 1 of 4 times I had hot water for my shower. If you don't mind cold showers, the rest of the hotel is pretty good.
Reviewed on Mar 2, 2026
Lake Wentworth Inn
427 Center St Wolfeboro NH
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Mar 30 to Mar 31
CA $163
CA $177 total
Mar 30 - Mar 31
includes taxes & fees
9.4/10 Exceptional! (523 reviews)
Courteous staff, room was clean. Convenient for our trip
Reviewed on Feb 18, 2026
The Windrifter Resort
337 South Main Street Wolfeboro NH
The price is CA $167 per night from Mar 29 to Mar 30
CA $167
CA $181 total
Mar 29 - Mar 30
includes taxes & fees
8.8/10 Excellent! (376 reviews)
We stayed for 2 days, it’s super cute, so convenient to be able to cook cook instead of going out. Room is good size, we had a beautiful Mountain View, the bed is lil on firm side if you like that, and the shower had nice hot water with great pressure! Would stay again for sure
Reviewed on Mar 24, 2026
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.
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.
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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.
