Title: Ossipee Vacation Packages & Trips 2026 from CA $1,576 | 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. ![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 $1,576 per person Jun 13 - Jun 17 found 17 hours ago Roundtrip flight included Toronto (YYZ) 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 $1,829 per person Jun 12 - Jun 16 found 1 day ago Roundtrip non-stop flight included Halifax (YHZ) to Boston (BOS) 8.6/10 Excellent! (1,395 reviews) Amenities consist of an ice machine and a tiny gym, for which they charged an "amenity fee"? Reviewed on Mar 18, 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 $1,837 per person Apr 21 - Apr 24 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Boston (BOS) 9.8/10 Exceptional! (1,001 reviews) Excellent hotel- restaurants, room service, all of the staff, spacious room with view, bathroom amenities. Great location. Able to take a leisurely walk along the water, and close to many restaurants and theatre district. Also easy to catch a taxi or uber. Wonderful setting with water and city view. Will definitely return! Reviewed on Mar 14, 2026 ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/f081d391_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay CA $2,315 per person May 29 - Jun 1 found 20 hours ago Roundtrip flight included Toronto (YTZ) to Boston (BOS) 9.6/10 Exceptional! (238 reviews) I went to raffles Boston for fiancés birthday and I called a week ahead to get the room decorated for her special day and when I showed up the room was not decorated, I then called and said they didn’t decorate the room like I asked so they asked if they could come up during dinner and decorate so I agreed. When we returned from dinner the room was “decorated”, the sign was hanging off the ceiling and decorations taped poorly and just looked awful. Very disappointed considering this is a expensive 5 start hotel Reviewed on Mar 12, 2026 ### Luxury 2BR near Cambridge Prospect Hill CA $2,677 per person Jun 13 - Jun 17 found 1 day ago Roundtrip flight included Toronto (YYZ) 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 $161 CA $234 total Apr 7 - Apr 8 includes taxes & fees 8.4/10 Very Good! (954 reviews) We had the most wonderful time for a girls weekend. We enjoyed the food all of the amenities and the staff was all lovely. We did, however have a really strange interaction with someone in the hot tub last night. Her name was Meghan was maybe mid 40s or 50s and had really short hair. She claimed ... Reviewed on Mar 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%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 Fully refundableReserve now, pay when you stay CA $144 CA $157 total Mar 24 - Mar 25 includes taxes & fees 7.8/10 Good! (1,000 reviews) Clean room, comfortable bed and nice hot shower. Quiet also Reviewed on Mar 17, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F03%2F2026&endDate=25%2F03%2F2026&selected=2601613&PinnedHotelID=2601613&HadPinnedHotel=true®ionId=553248634999059097) ![Green Granite Inn, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/2000000/1220000/1220000/1219930/29fdc6b0_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 $87 CA $94 total Apr 12 - Apr 13 includes taxes & fees 6.6/10 (1,230 reviews) A little outdated but very clean, nice staff. Kids had a blast Reviewed on Mar 17, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=1219930&PinnedHotelID=1219930&HadPinnedHotel=true®ionId=553248634999059097) [See all 1,976 properties in Ossipee](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F03%2F2026&endDate=21%2F03%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