Title: Ossipee Vacation Packages & Trips 2026 from CA $1,283 | Expedia.ca [Hotels in Ossipee](https://expedia.ca/Ossipee-Hotels.d553248634999059097.Travel-Guide-Hotels)[Vacation Rentals in Ossipee](https://expedia.ca/Ossipee-Vacation-Rentals.d553248634999059097.Travel-Guide-VacationRentals)[Ossipee Car Rentals](https://expedia.ca/Car-Rentals-In-Ossipee.d553248634999059097.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248634999059097/38cd9a94-49a6-4bb5-9299-f81dd0e93b39.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Ossipee 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 Ossipee Vacation With all your travel plans organized before you set off, our Ossipee vacation packages let you simply focus on vacationing! One place to base yourself in this interesting city is Chocorua Ski and Beach, which is good for camping and nature. You'll want to sightsee during your trip to Ossipee. Make time for big-name attractions such as [Province Lake](https://www.expedia.ca/Province-Lake-New-Hampshire.d553248635976196840.Vacation-Attraction), [Wentworth State Park](https://www.expedia.ca/Wentworth-State-Park-Wolfeboro.d6333338.Vacation-Attraction) and [Sap House Meadery](https://www.expedia.ca/Sap-House-Meadery-Center-Ossipee.d553248621532667875.Vacation-Attraction). Don't put off your visit to this city any longer. Your perfect Ossipee vacation is a couple of clicks away with Expedia. ## Top Ossipee Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Harbor Hotel North End CA $1,283 per person May 8 - May 10 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.8/10 Exceptional! (1,001 reviews) Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub. Reviewed on Mar 23, 2026 ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/54f3deb7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Boston Downtown Boston CA $3,140 per person Jun 13 - Jun 17 found 1 day ago Roundtrip non-stop flight included Toronto (YTZ) to Boston (BOS) 9.6/10 Exceptional! (1,004 reviews) clean room. friendly and helpful staff. good breakfast in reasonable price. hope they have a boutique store to sell Langham signature products, especially the home fragrance products. Reviewed on Mar 29, 2026 ![The Inn at Hastings Park, Relais & Chateaux - Boston](https://images.trvl-media.com/lodging/8000000/7990000/7980700/7980601/8dcd0e80_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Hastings Park, Relais & Chateaux - Boston CA $1,673 per person Jun 13 - Jun 17 found 1 day ago Roundtrip non-stop flight included Toronto (YTZ) to Boston (BOS) 9.6/10 Exceptional! (252 reviews) Excellent experience- clean and very helpful staff Reviewed on Mar 9, 2026 ![Eurostars The Boxer](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/ee935931_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars The Boxer West End CA $1,402 per person Jun 22 - Jun 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Boston (BOS) 8.6/10 Excellent! (1,395 reviews) Great hotel, in the middle of downtown, walking distance from td garden, friendly staff and great amenities, will be back for sure Reviewed on Mar 30, 2026 ![Summer House Hotel](https://images.trvl-media.com/lodging/82000000/81080000/81071500/81071424/554f58d3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Summer House Hotel CA $1,771 per person Jun 18 - Jun 21 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Boston (BOS) No reviews ## Ready to book your vacation to Ossipee? Choose your dates ## Ossipee Hotel Deals ![Mill Falls Resort Collection at the Lake](https://images.trvl-media.com/lodging/37000000/36900000/36897600/36897575/1b02a295_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Mill Falls Resort Collection at the Lake 281 Daniel Webster Hwy Meredith NH CA $138 CA $209 total Apr 16 - Apr 17 includes taxes & fees 8.4/10 Very Good! (961 reviews) Great off season stay. Enjoyed the pool and hot tub. Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=36897575&PinnedHotelID=36897575&HadPinnedHotel=true®ionId=553248634999059097) ![Best Western Plus Landmark Inn](https://images.trvl-media.com/lodging/3000000/2610000/2601700/2601613/80e088ad_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Landmark Inn 480 Main Street Laconia NH CA $146 CA $159 total Apr 16 - Apr 17 includes taxes & fees 7.8/10 Good! (1,002 reviews) Yesss Reviewed on Apr 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=2601613&PinnedHotelID=2601613&HadPinnedHotel=true®ionId=553248634999059097) ![Home2 Suites by Hilton North Conway](https://images.trvl-media.com/lodging/64000000/63120000/63112100/63112040/0c005b04_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Home2 Suites by Hilton North Conway 1439 White Mountain Hwy North Conway NH Fully refundableReserve now, pay when you stay CA $135 CA $147 total Apr 13 - Apr 14 includes taxes & fees 9.4/10 Exceptional! (686 reviews) The perfect stay in North Conway! Reviewed on Apr 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=13%2F04%2F2026&endDate=14%2F04%2F2026&selected=63112040&PinnedHotelID=63112040&HadPinnedHotel=true®ionId=553248634999059097) [See all 2,004 properties in Ossipee](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F04%2F2026&endDate=04%2F04%2F2026®ionId=553248634999059097) 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) ## 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