West Ossipee Vacation Packages
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Top West Ossipee vacation deals
- Inn at Diamond Cove
Oct 8 - Oct 11Inn at Diamond Cove + Flight
Portland3 nights3.5 star property8.8/10 - Excellent (201 reviews)"Friendly staff, went above and beyond."Reviewed July 20, 2026Roundtrip • Toronto (YTO) - Portland (PWM)YTZ - BOS • Nonstop BOS - YTZ • NonstopCA $1,259CA $965found 2 hours agoper traveller - Ogunquit River Inn & Suites
Aug 28 - Sept 3Ogunquit River Inn & Suites + Flight
Moody6 nights3.0 star property9.0/10 - Wonderful (1,017 reviews)Roundtrip • Ottawa (YOW) - Portland (PWM)YOW - PWM • 1 stop PWM - YOW • 1 stopCA $2,480CA $1,721found 22 hours agoper traveller - The Meadowmere Resort
Aug 28 - Sept 3The Meadowmere Resort + Flight
Ogunquit6 nights2.5 star property8.6/10 - Excellent (1,001 reviews)"I requested a room accessible for my 90 year old mother with a walker. We got that. I asked the front desk woman if there was another entrance to the pool because the one at the entrance had many stairs. She said no. Another traveler in the lobby told me there is one around the back. The staff member said they never took her around the property and trained her when the woman said that. They play music all day and night until 10:30pm outside my room by a speaker. I requested it be turned off and..."Reviewed July 22, 2026Roundtrip • Ottawa (YOW) - Portland (PWM)YOW - PWM • 1 stop PWM - YOW • 1 stopCA $2,929CA $2,062found 19 hours agoper traveller - Portland Harbor Hotel
Aug 28 - Sept 3Portland Harbor Hotel + Flight
Downtown Portland6 nights4.0 star property9.4/10 - Exceptional (1,789 reviews)Roundtrip • Ottawa (YOW) - Portland (PWM)YOW - PWM • 1 stop PWM - YOW • 1 stopCA $3,122CA $2,277found 21 hours agoper traveller - Evalina Hotel
Sept 25 - Sept 28Evalina Hotel + Flight
Downtown Portland3 nights2.5 star property10/10 - Exceptional (5 reviews)"It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure."Reviewed June 28, 2026Roundtrip • Toronto (YTO) - Portland (PWM)YYZ - PWM • 1 stop PWM - YYZ • 1 stopCA $2,529CA $2,026found 1 day agoper traveller
West Ossipee Hotel Deals
Frequently Asked Questions
How much does a West Ossipee vacation package cost?
You can snap up a vacation package to this popular destination from CA $965 on Expedia. But how much your vacation to West Ossipee costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to West Ossipee?
If you're looking to snag a cheap West Ossipee vacation package, consider travelling in November, December and January. You'll typically find lower prices on flights and hotels during these months — ideal for travellers wishing to save money.
How many days is enough for West Ossipee?
With about 2 days, you'll have enough time to enjoy popular neighbourhoods like Chocorua and Chocorua Ski and Beach during your West Ossipee vacation. Make sure to also add Sap House Meadery and Remick Country Doctor Museum and Farm to your sightseeing list. In the mood for more adventures? Consider venturing outside of West Ossipee on day trips and tours.
How to find the best West Ossipee package deals?
Use Expedia's handy filters to help you find some unbeatable West Ossipee package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for West Ossipee package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a West Ossipee vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized West Ossipee vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to West Ossipee?
If you have your West Ossipee travel dates locked in, book as soon as you can to snap up some outstanding deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to West Ossipee?
- Choose when to travel: Check your diary and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to visit West Ossipee.
- Calculate your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your hotel will probably be the largest expense during your trip to West Ossipee.
- Decide how long to go for: Now that you're up to speed on West Ossipee, you can figure out the ideal length of your vacation. Put together a draft plan and allocate enough time to get through everything on your must-do list.
- Combine your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the ideal West Ossipee vacation package for you.