Ossipee Holidays

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Top Flight + Hotel Deals in Ossipee

Price found within the past 48 hours. Click for updated prices.
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
per person
8 Oct - 12 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8/10 Very Good! (566 reviews)
The location is good (in terms of convenient to most city attractions) and the space of the apartment was decent. Nice sized kitchen with good appliances. Everything was very clean. We did not like the front desk staff at all. They were extremely unprofessional and rude during both check-in and out. Plus, we had to wait both times because no one was at front desk to help us.

Reviewed on 27 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
18 Sept - 22 Sept
found 18 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on 28 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
18 Sept - 22 Sept
found 18 hours ago
Return flight included
Dublin (DUB) 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 Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
per person
8 Oct - 12 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (1,964 reviews)
Family of 5, including 3 young adult sons, 2 night stay. We had 2 interconnecting rooms which were huge, and very comfortable. We used the roof top pool each evening and early morning, which was amazing. Pool staff were so friendly. Gym was good, too. We didn't eat there, but great breakfast option directly opposite the hotel, and restaurants within 10 minutes' walk. Would highly recommend this lovely hotel.

Reviewed on 30 Jul 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
per person
8 Oct - 12 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,087 reviews)
Check in was very good. Property sleek and minimalist. Very clean and well maintained. Shops, restaurants a few minutes walk away. Too bad the valet gives incorrect directions to local sites.

Reviewed on 29 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 €70 per night from 24 Aug to 25 Aug
€70
24 Aug - 25 Aug
includes taxes & fees
6.8/10 (1,242 reviews)
"The Green Granite was clean and convenient for a fair price. Enjoyed the indoor pool, although the atea could use some updates. Couldnt beat the location and it was nice to have breakfast included."

Reviewed on 27 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 €259 per night from 3 Aug to 4 Aug
€259
3 Aug - 4 Aug
includes taxes & fees
8.2/10 Very Good! (754 reviews)
"The collection of properties was very nice and pleasant, the staff in every area was kind and accommodating, the ambiance was nice and the general aesthetic was sweet. The Palmer Inn was somewhat rundown and had several things that needed addressing. In our specific hotel room, the beds were very ..."

Reviewed on 30 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 €115 per night from 10 Aug to 11 Aug
€115
10 Aug - 11 Aug
includes taxes & fees
7.6/10 Good! (1,000 reviews)
"Price was right and it was close to the music venue. Bed was very comfy."

Reviewed on 29 Jul 2025

Best Western Plus Landmark Inn
See all 1,984 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 €1,128 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.