Ossipee Holidays

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    Save up to €900 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Flight + Hotel Deals in Ossipee

Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was €1,149, price is now €818 per person
€818
per person
4 Dec - 7 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
The hotel grounds are extremely well maintained; the views of the water and benches to relax on are fantastic! We had a great stay with our two teenagers. It was out of the hustle and bustle of the city. A wonderful place!

Reviewed on 26 Oct 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was €3,747, price is now €2,601 per person
€2,601
per person
26 Nov - 1 Dec
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Great hotel for the weekend! My husband and I were celebrating our anniversary!

Reviewed on 25 Oct 2026

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was €1,248, price is now €979 per person
€979
per person
1 Dec - 6 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (3,468 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was €3,365, price is now €2,710 per person
€2,710
per person
26 Nov - 1 Dec
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
设施很新，SPA桑拿体验特别好，晚餐气氛很棒

Reviewed on 20 Oct 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was €3,815, price is now €3,102 per person
€3,102
per person
26 Nov - 1 Dec
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (465 reviews)

Top hotels in Ossipee

The Green Granite North Conway, an Ascend Collection Hotel

The Green Granite North Conway, an Ascend Collection Hotel

2.5 out of 5
1515 White Mountain Hwy North Conway NH
Fully refundable
The price is €73 per night from 16 Nov to 17 Nov
€73
16 Nov - 17 Nov
includes taxes & fees
6.6/10 (286 reviews)
"Breakfast was great. Beds were old and squeaky, Needs an update, but friendly staff. You definitely get what you pay for here."

Reviewed on 26 Oct 2026

The Green Granite North Conway, an Ascend Collection Hotel
Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

3 out of 5
281 Daniel Webster Hwy Meredith NH
The price is €194 per night from 28 Oct to 29 Oct
€194
28 Oct - 29 Oct
includes taxes & fees
8.4/10 Very good! (1,007 reviews)
"Check in was at 4pm, room wasn't ready until after 5pm., no coffeemaker in the room, balcony wolud have been nice if it wasn't covered in bird excrement."

Reviewed on 26 Oct 2026

Mill Falls Resort Collection at the Lake
Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

2.5 out of 5
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
The price is €98 per night from 1 Nov to 2 Nov
€98
1 Nov - 2 Nov
includes taxes & fees
Best Western Plus Landmark Inn
See all 2,083 properties in Ossipee
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.

Stay near popular Ossipee attractions

Duncan Lake

Commune with nature and explore the great outdoors at Duncan Lake during your travels in Ossipee.
See properties

Frequently asked questions

How much does an Ossipee holiday package cost?
You can grab a holiday package to this destination from €818 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.