Title: Ossipee Vacation Packages & Trips 2026 from CA $614 | 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. ![Lakeside Inn](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/b04e2b5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lakeside Inn CA $614 per person May 7 - May 12 found 6 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 7.6/10 Good! (2,303 reviews) The room I had was adequate for one night. It was in need of repair and a paint job to cover the many plaster patches on the walls. The front desk staff were friendly and welcoming. Reviewed on Feb 4, 2026 ![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 $2,327 per person Apr 27 - May 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.8/10 Exceptional! (1,005 reviews) Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem. Reviewed on Jan 25, 2026 ![The Colonnade Hotel Back Bay](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/f43e7537_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Colonnade Hotel Back Bay Back Bay CA $942 per person Mar 21 - Mar 25 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Boston (BOS) 9.2/10 Wonderful! (2,268 reviews) Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave.. Reviewed on Feb 2, 2026 ![The Whitney Hotel](https://images.trvl-media.com/lodging/30000000/29870000/29866100/29866090/59f2dc0e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Whitney Hotel Beacon Hill CA $1,254 per person Mar 21 - Mar 25 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Boston (BOS) 9.6/10 Exceptional! (482 reviews) Excellent property conveniently located in Beacon Hill. Rooms are a tad on the small side but well appointed and clean. Reviewed on Feb 7, 2026 ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/0f66f064_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay CA $1,942 per person Mar 21 - Mar 25 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Boston (BOS) 9.6/10 Exceptional! (181 reviews) Attention to guest needs. Reviewed on Feb 8, 2026 ## 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 $131 CA $200 total Mar 2 - Mar 3 includes taxes & fees 8.2/10 Very Good! (934 reviews) Nice room great view Reviewed on Jan 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F03%2F2026&endDate=03%2F03%2F2026&selected=36897575&PinnedHotelID=36897575&HadPinnedHotel=true®ionId=553248634999059097) ![Fireside Inn & Suites Gilford](https://images.trvl-media.com/lodging/2000000/1540000/1536900/1536870/c9dd5729_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fireside Inn & Suites Gilford 17 Harris Shore Road Gilford NH Fully refundableReserve now, pay when you stay CA $182 CA $198 total Mar 1 - Mar 2 includes taxes & fees 8.8/10 Excellent! (937 reviews) We were so impressed with the room. The service was excellent and all the staff friendly and helpful. The pool and hot tub were wonderful to enjoy. The hotel was sooo clean. The breakfast in the morning was an added bonus. Would definitely stay here again. Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=1536870&PinnedHotelID=1536870&HadPinnedHotel=true®ionId=553248634999059097) ![Green Granite Inn, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/2000000/1220000/1220000/1219930/84e2004b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Green Granite Inn, an Ascend Collection Hotel 1515 White Mountain Hwy North Conway NH Fully refundable CA $103 CA $111 total Mar 4 - Mar 5 includes taxes & fees 6.6/10 (1,223 reviews) The staff were amazing and helpful. There is a beautiful lobby with a huge fireplace and plenty of space for guests to sit and chat, play a game, or just vibe after a day of skiing. Super relaxing. Nice full breakfast with plenty of options. Perfect location near everything. I'm glad we discovered ... Reviewed on Jan 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=1219930&PinnedHotelID=1219930&HadPinnedHotel=true®ionId=553248634999059097) [See all 1,944 properties in Ossipee](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F02%2F2026&endDate=13%2F02%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