Title: Wolfeboro Vacation Packages & Trips 2026 from CA $1,204 | Expedia.ca [Hotels in Wolfeboro](https://expedia.ca/Wolfeboro-Hotels.d176096.Travel-Guide-Hotels)[Vacation Rentals in Wolfeboro](https://expedia.ca/Wolfeboro-Vacation-Rentals.d176096.Travel-Guide-VacationRentals)[Flights to Wolfeboro](https://expedia.ca/Cheap-Flights-To-Wolfeboro.d176096.Travel-Guide-Flights)[Wolfeboro Car Rentals](https://expedia.ca/Car-Rentals-In-Wolfeboro.d176096.Car-Rental-Guide) ![](https://images.trvl-media.com/place/176096/bb9dff28-a6cb-406a-befb-6543384112c8.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Wolfeboro Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Lake-Wentworth-Laconia.d553248635976195960.Vacation-Attraction), [Allen Albee Beach](https://www.expedia.ca/Allen-Albee-Beach-Wolfeboro.d6271252.Vacation-Attraction) and [Kingswood Golf Club](https://www.expedia.ca/Kingswood-Golf-Club-Wolfeboro.d553248621558657106.Vacation-Attraction) 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 Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Portland Harborview Downtown Portland CA $1,204 per person Feb 21 - Feb 28 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 8.8/10 Excellent! (1,001 reviews) Front end lady very rude. Long hair, didn’t get her name. Young gentleman very nice, solved a misunderstanding with great customer service. Reviewed on Dec 4, 2025 ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Harbor Hotel Downtown Portland CA $1,259 per person Feb 21 - Feb 28 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.2/10 Wonderful! (1,668 reviews) it's a bit worn out we felt and more expensive that it should have been Reviewed on Dec 16, 2025 ![Blind Tiger Portland - Danforth Street.](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/4e66cf6e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Blind Tiger Portland - Danforth Street. West End CA $1,652 per person Feb 21 - Feb 28 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.6/10 Exceptional! (161 reviews) The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here! Reviewed on Nov 23, 2025 ![Inn By The Sea](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/d0fca35d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn By The Sea CA $1,933 per person Feb 21 - Feb 28 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.4/10 Exceptional! (288 reviews) Room was ready early friendly staff and room is better than expected Reviewed on Nov 16, 2025 ![Embassy Suites by Hilton Portland Maine](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/cbc24127_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Embassy Suites by Hilton Portland Maine CA $1,243 per person Feb 21 - Feb 28 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.4/10 Exceptional! (1,121 reviews) Because of an early morning out patient surgery appointment I was unable to enjoy the breakfast buffet. On my last visit I did and loved it, especially my made to order omelette! Reviewed on Dec 16, 2025 ## Ready to book your vacation to Wolfeboro? Choose your dates ## Wolfeboro Hotel Deals ![Lake Wentworth Inn](https://images.trvl-media.com/lodging/38000000/37390000/37389100/37389082/db781d80_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lake Wentworth Inn 427 Center St Wolfeboro NH CA $148 CA $161 total Dec 21 - Dec 22 includes taxes & fees 9.4/10 Exceptional! (516 reviews) Clean and the staff was very helpful and kind. Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=37389082&PinnedHotelID=37389082&HadPinnedHotel=true®ionId=176096) ![The Wolfeboro Inn](https://images.trvl-media.com/lodging/2000000/1850000/1849000/1848958/ce903410_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Wolfeboro Inn 90 N Main St Wolfeboro NH Fully refundableReserve now, pay when you stay 8/10 Very Good! (547 reviews) Room was very comfy and quiet Reviewed on Dec 14, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=1848958&PinnedHotelID=1848958&HadPinnedHotel=true®ionId=176096) [](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=1848958&PinnedHotelID=1848958&HadPinnedHotel=true®ionId=176096) ![The Windrifter Resort](https://images.trvl-media.com/lodging/78000000/77130000/77127800/77127743/733d38d3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Windrifter Resort 337 South Main Street Wolfeboro NH CA $155 CA $168 total Dec 22 - Dec 23 includes taxes & fees 8.6/10 Excellent! (364 reviews) Another great stay!! Reviewed on Nov 25, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F12%2F2025&endDate=23%2F12%2F2025&selected=77127743&PinnedHotelID=77127743&HadPinnedHotel=true®ionId=176096) [See all 2,060 properties in Wolfeboro](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=18%2F12%2F2025&endDate=19%2F12%2F2025®ionId=176096) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### 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. [](https://expedia.ca/Allen-Albee-Beach-Wolfeboro.d6271252.Vacation-Attraction) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app