West Ossipee Vacation Packages
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Top West Ossipee vacation deals
- Ogunquit River Inn & Suites
Sept 24 - Sept 27Ogunquit River Inn & Suites + Flight
Moody3 nights3.0 star property9.0/10 - Wonderful (1,000 reviews)"All the five stars I gave this place said it all… The staff was obviously well versed and management was very creative… I don’t remember getting Little packages of Q tips anywhere else… Loved this place"Reviewed August 3, 2026Roundtrip • Montreal (YMQ) - Portland (PWM)YUL - BOS • Nonstop BOS - YUL • 1 stopCA $975CA $757found 1 day agoper traveller - Evalina Hotel
Oct 18 - Oct 24Evalina Hotel + Flight
Downtown Portland6 nights2.5 star property10/10 - Exceptional (8 reviews)"Evalina was more than we expected. Super clean and has every convenience item imaginable. The beds were super comfortable. The communication was spectacular which made everything from check in to checkout s smooth. We will definitely be back and hopefully for a longer stay next time."Reviewed August 4, 2026Roundtrip • Toronto (YTO) - Portland (PWM)YYZ - PWM • 1 stop PWM - YYZ • 1 stopCA $3,949CA $2,854found 14 hours agoper traveller - Blind Tiger Portland - Danforth Street.
Oct 18 - Oct 22Blind Tiger Portland - Danforth Street. + Flight
West End4 nights3.5 star property9.6/10 - Exceptional (189 reviews)"This hotel is amazing. The rooms, beds, and all the details are so incredible. I wish I could have stayed longer. Check in was a breeze as well. You can tell they take a lot of care and thought into the property. I will definitely be back"Reviewed July 25, 2026Roundtrip • Toronto (YTO) - Portland (PWM)YYZ - PWM • 1 stop PWM - YYZ • 1 stopCA $3,374CA $2,607found 11 hours agoper traveller - Portland Regency Hotel & Spa
Oct 18 - Oct 24Portland Regency Hotel & Spa + Flight
Downtown Portland6 nights3.5 star property9.4/10 - Exceptional (1,717 reviews)Roundtrip • Toronto (YTO) - Portland (PWM)YYZ - PWM • 1 stop PWM - YYZ • 1 stopCA $2,610CA $2,024found 14 hours agoper traveller - The Docent's Collection at 121 Middle Street
Oct 18 - Oct 24The Docent's Collection at 121 Middle Street + Flight
Downtown Portland6 nights3.5 star property9.6/10 - Exceptional (369 reviews)"We had a great stay here. The space was large, well appointed, and very comfortable. Highly recommend!"Reviewed August 4, 2026Roundtrip • Toronto (YTO) - Portland (PWM)YYZ - PWM • 1 stop PWM - YYZ • 1 stopCA $2,694CA $2,146found 14 hours agoper traveller
West Ossipee Hotel Deals
"No coffee pot in room"
"Room was very clean an outdated but served the purpose (I had a 2 night stay)."
"I truly loved the place so relaxing and enjoyable , me and my boyfriend will definitely be back . During the summer is the best time for relaxation ."
"We were a group of American Legion Riders and with the setup of the front porch, tables and chairs with rocking chairs too, we were able to relax, visit, laugh and talk so comfortably with each other. Great place to stay!!"
"La chambre était très chaude à notre arrivée, ça puait l'humidité, il y avait beaucoup de poussière et de toiles d'araignées. On nous a vendu "des petites viennoiseries et café" pour déjeuner, mais il n'y avait rien. Il n'y avait pas de personnel sur place, la réception était fermée pour toute la durée de notre séjour. Très déçus, car notre première visite à cet endroit avait été bonne, mais nous n'y retournerons pas après cette deuxième expérience."
"Staff is extremely friendly and helpful, the room was actually really neat with it having an older charm to it that you can't find anymore in North Conway and the balcony with the view was insane. The bathroom was huge and the bed was pretty comfy. I have no complaints and will definitely be back. To those expecting Hilton qualities at this charming OG inn...there's one down the road. You cant beat the price nor the view."
"This is a great location if you’re going up to North Conway close to the outlets and any of the cycle tubing trips. It is even on the soccer river so if you just wanna go and hang out on the cycle, you’re already there would highly recommend."
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 $757 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.