Ossipee Holidays
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Top Ossipee flight + hotel deals
Price found within the past 48 hours. Click for updated prices.
- Eurostars The Boxer
15 Oct - 20 OctEurostars The Boxer + Flight
West End5 nights4.0 star property8.8/10 - Excellent (1,536 reviews)Return • Dublin (DUB) - Boston (BOS)DUB - BOS • 1 stop BOS - DUB • Direct€1,846€1,246found 11 hours agoper traveller - Boston Harbor Hotel
15 Oct - 20 OctBoston Harbor Hotel + Flight
North End5 nights5.0 star property9.8/10 - Exceptional (1,004 reviews)Return • Dublin (DUB) - Boston (BOS)DUB - BOS • 1 stop BOS - DUB • Direct€3,397€1,960found 11 hours agoper traveller - The Godfrey Hotel Boston
15 Oct - 20 OctThe Godfrey Hotel Boston + Flight
Downtown Boston5 nights4.0 star property9.6/10 - Exceptional (5,136 reviews)"Location was great for site seeing. Super close to start of Freedom Trail. Pretty much everything was walkable. Staff were helpful. Pillows were terrible."Reviewed July 26, 2026Return • Dublin (DUB) - Boston (BOS)DUB - BOS • 1 stop BOS - DUB • Direct€2,130€1,437found 11 hours agoper traveller - The Colonnade Hotel Back Bay
15 Oct - 20 OctThe Colonnade Hotel Back Bay + Flight
Back Bay5 nights4.0 star property9.2/10 - Wonderful (2,387 reviews)"wonderful staff, great location with beautiful views. will be back"Reviewed July 27, 2026Return • Dublin (DUB) - Boston (BOS)DUB - BOS • 1 stop BOS - DUB • Direct€2,021€1,422found 11 hours agoper traveller - Battery Wharf Hotel, Boston Waterfront
15 Oct - 20 OctBattery Wharf Hotel, Boston Waterfront + Flight
North End5 nights4.5 star property8.8/10 - Excellent (1,915 reviews)Return • Dublin (DUB) - Boston (BOS)DUB - BOS • 1 stop BOS - DUB • Direct€2,125€1,579found 11 hours agoper traveller
Ossipee Hotel Deals
7.4 out of 10, Good, (502 reviews)
7.4/10
Good
(502 reviews)
"Staff were friendly and helpful, and our room comfortable. Beds comfortable. The location is great and that probably how they get away with charging the rates they do with a very outdated property. Breakfast was laughable - powdered eggs and tater tots on week ends, with two choices of dry cereal - one looked like an assortment of left overs - Cheerios and lucky charms? Coffee but no OJ - pink lemonade dispensed in the OJ dispenser. There was yogurt and make your own waffles.
But again, clean...
The price is €80
€80
includes taxes & fees
28 Jul - 29 Jul
7.8 out of 10, Good, (267 reviews)
7.8/10
Good
(267 reviews)
"Clean and well priced. Not charming inside, but you get what you pay for, right?"
The price is €84
€84
includes taxes & fees
28 Jul - 29 Jul
7.2 out of 10, Good, (652 reviews)
7.2/10
Good
(652 reviews)
"our room was disgusting, we had moldy sheets bugs in our room. There was some sort of animal urine at our door. The furniture was stained and the front desk was super rude and unhelpful with our complaints i would not recommend to anyone."
The price is €85
€85
includes taxes & fees
2 Aug - 3 Aug
9.4 out of 10, Exceptional, (567 reviews)
9.4/10
Exceptional
(567 reviews)
"I've never felt as unwelcome as I did at this property. The property was not staffed, which was concerning because I arrived after nightfall and there was very poor lighting all around the property. I had to speak to a ring camera for assistance w/checking in, while standing outside in the dark.
The associate then told me, via telephone, they had tried to reach me regarding checking in. I asked, "Tried to reach me how?" Her response was, "On your cell phone." I asked, "As in you left me a...
The price is €180
€180
includes taxes & fees
29 Jul - 30 Jul
8.8 out of 10, Excellent, (209 reviews)
8.8/10
Excellent
(209 reviews)
The price is €161
€161
includes taxes & fees
28 Jul - 29 Jul
8.8 out of 10, Excellent, (409 reviews)
8.8/10
Excellent
(409 reviews)
"The front desk clerk Adrian, was very helpful with the questions I had and gave great advice. The apartment was nice and was very comfortable for are stay."
The price is €159
€159
includes taxes & fees
10 Aug - 11 Aug
9.0 out of 10, Wonderful, (1,005 reviews)
9.0/10
Wonderful
(1,005 reviews)
The price is €182
€182
includes taxes & fees
2 Aug - 3 Aug
9.0 out of 10, Wonderful, (535 reviews)
9.0/10
Wonderful
(535 reviews)
"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!!"
The price is €114
€114
includes taxes & fees
28 Jul - 29 Jul
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.
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.
Frequently Asked Questions
How much does an Ossipee holiday package cost?
You can grab a holiday package to this destination from €1,246 on Expedia. But how much your holiday to Ossipee costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Ossipee?
To score cheap Ossipee holiday packages, plan your trip outside of busy periods like public holidays and major festivals. You'll generally find better availability and lower prices when it's less busy.
How many days is enough for Ossipee?
With a well-organised itinerary, you can easily tick off the main Ossipee attractions in a few days. But if you prefer to discover hidden gems or go on day tours, consider booking your Ossipee holiday for longer.
How to find the best Ossipee package deals?
Use Expedia's handy filters to help you find some unbeatable 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 want to save, plan your adventure for midweek, or browse for Ossipee package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book an Ossipee holiday as a package?
You can enjoy significant savings on your Ossipee retreat by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to view some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Ossipee?
Secure incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Ossipee escape.
How to plan a trip to Ossipee?
- Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Ossipee.
- Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to experiences and flights. Your accommodation will probably be the biggest expense during your trip to Ossipee.
- Decide how long to go away for: Now that you're more familiar with Ossipee, you can work out the perfect length of your break. Create a draft itinerary and allocate enough time to cover everything you want to do.
- Bundle your airfare and accommodation: Once you've nailed down your dates and duration, lock in the right Ossipee holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.