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 $1,520, price is now CA $1,284 per person
CA $1,284
per person
May 25 - May 29
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
We could have moved right in and been happy for life. Flawless.
Reviewed on Mar 30, 2026
Inn By The Sea
Price was CA $2,582, price is now CA $2,226 per person
CA $2,226
per person
May 25 - May 29
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Portland (PWM)
9.4/10 Exceptional! (304 reviews)
This was my first trip away since having kids 12 years ago. The staff was very friendly, helpful and attentive. The parking lot, lobby, halls and room were very clean. Our dinner and breakfast at the Inn were absolutely delicious. The ingredients were fresh and the flavors complimented each other well. It was difficult to make a choice on what to order. We didn't have a pet with us but did see several dogs during dining and were impressed with dog menu. I would highly recommend to anyone to stay at the Inn and if you are unable to at least have a meal in the restaurant. We are already planning a longer stay next time.
Reviewed on Mar 30, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $2,022, price is now CA $1,791 per person
CA $1,791
per person
May 25 - May 29
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) 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
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $3,212, price is now CA $2,918 per person
CA $2,918
per person
Jun 26 - Jun 28
found 20 hours ago
Roundtrip flight included
Presque Isle (PQI) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
Beautiful space, clean room, friendly and accommodating staff, excellent location
Reviewed on Apr 5, 2026
Wolfeboro Hotel Deals
The Wolfeboro Inn
90 N Main St Wolfeboro NH
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Apr 19 to Apr 20
CA $187
CA $240 total
Apr 19 - Apr 20
includes taxes & fees
8.2/10 Very Good! (565 reviews)
This hotel has a fabulous location regarding Lake Winnipesaukee. I stayed there in March of 2025 and 2026 and both times paid a "resort fee" which consisted of nothing. The hotel staff were very nice. My room was clean, but run down. The furniture was scratched, gauged, and set up on blocks of wood. ...
Reviewed on Apr 2, 2026
Lake Wentworth Inn
427 Center St Wolfeboro NH
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Apr 7 to Apr 8
CA $169
CA $184 total
Apr 7 - Apr 8
includes taxes & fees
9.4/10 Exceptional! (527 reviews)
Very nice comfortable room. The front desk staff was awesome. Only a few minutes from downtown.
Reviewed on Apr 6, 2026
The Windrifter Resort
337 South Main Street Wolfeboro NH
The price is CA $156 per night from Apr 12 to Apr 13
CA $156
CA $169 total
Apr 12 - Apr 13
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.
