Ossipee Holidays

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    Save up to €185 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Ossipee

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
per person
13 Sept - 19 Sept
found 1 day ago
Return direct flight included
Shannon (SNN) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Everything outstanding

Reviewed on 19 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
13 Sept - 19 Sept
found 1 day ago
Return direct flight included
Shannon (SNN) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on 14 Jul 2025

The Boxer

The Boxer

4 out of 5
West End
Save 100% on your flight
per person
13 Sept - 19 Sept
found 1 day ago
Return direct flight included
Shannon (SNN) to Boston (BOS)
8.6/10 Excellent! (1,236 reviews)
Great area of town and around the corner from the venue we were attending. Didn't like only one ice machine and only located on the third floor.

Reviewed on 19 Jul 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Save 100% on your flight
per person
13 Sept - 19 Sept
found 1 day ago
Return direct flight included
Shannon (SNN) to Boston (BOS)
9.2/10 Wonderful! (1,087 reviews)
Good Location in Back Bay. Older Hotel and rooms but bed was great. Staff friendly. Only stayed there one night.

Reviewed on 17 Jul 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Save 100% on your flight
per person
13 Sept - 19 Sept
found 1 day ago
Return direct flight included
Shannon (SNN) to Boston (BOS)
8/10 Very Good! (566 reviews)
Pros- Apartment itself is extremely spacious and clean/modern. Quiet, easy check in/check out process Cons- Probably won’t be able to hold your bags on the weekends prior to 4 which sucked. Fitness facilities out of order.

Reviewed on 4 Jul 2025

Top hotels in Ossipee

Green Granite Inn, Ascend Hotel Collection

Green Granite Inn, Ascend Hotel Collection

2.5 out of 5
1515 White Mountain Hwy, North Conway, NH
Fully refundableReserve now, pay when you stay
The price is €84 per night from 3 Aug to 4 Aug
€84
3 Aug - 4 Aug
includes taxes & fees
6.8/10 (1,213 reviews)
"This hotel honestly exceeded our expectations! The rooms were huge, the pool was clean and lots of tables and chairs. A playground was also a fun activity for our preschoolers. The beds were super comfortable and the breakfast was plentiful and good! Eggs, sausage, pancakes, bagels/breads/muffins, ..."

Reviewed on 16 Jul 2025

Green Granite Inn, Ascend Hotel Collection
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 €220 per night from 21 Jul to 22 Jul
€220
21 Jul - 22 Jul
includes taxes & fees
8.2/10 Very Good! (737 reviews)
"Loved everything!!!"

Reviewed on 13 Jul 2025

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 €110 per night from 10 Aug to 11 Aug
€110
10 Aug - 11 Aug
includes taxes & fees
7.6/10 Good! (1,004 reviews)
"Overall, we were happy with our stay. Our room and the property itself was clean. Aside from the person who checked us in every other person we interacted with for staff was great. Person who checked us in didn’t even acknowledge us with the hello or a smile, simply said license and credit card when ..."

Reviewed on 11 Jul 2025

Best Western Plus Landmark Inn
See all 1,992 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.

Frequently asked questions

How much does an Ossipee holiday package cost?
You can grab a holiday package to this destination from €1,069 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.