Ossipee Vacation Packages

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Your Ossipee Vacation

With all your travel plans organized before you set off, our Ossipee vacation packages let you simply focus on vacationing! One place to base yourself in this interesting city is Chocorua Ski and Beach, which is good for camping and nature. You'll want to sightsee during your trip to Ossipee. Make time for big-name attractions such as Province Lake, Wentworth State Park and Sap House Meadery. Don't put off your visit to this city any longer. Your perfect Ossipee vacation is a couple of clicks away with Expedia.

Top Ossipee Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
per person
Aug 22 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (3,247 reviews)
I would come Back to this property

Reviewed on Jul. 19, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
Valet service was quite slow when requesting car

Reviewed on Jul. 18, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 Jul. 14, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Aug 22 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (413 reviews)
The room was large, clean and quiet. There are plenty of restaurants within walking distance. The bed was comfortable. Overall, a great place to stay and close to MGH which is a key reason for booking.

Reviewed on Jul. 12, 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
The property was beautiful and very clean.. room was amazing and spacious. The only negative things were the sheets were not cooling at all and the air conditioning did not go down low enough for comfort at night. Also, the restaurants were way to expensive. Its like paying double for your room if you eat there..

Reviewed on Jul. 19, 2025

Ready to book your vacation to Ossipee?

 

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Ossipee Hotel Deals

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 CA $124 per night from Aug 3 to Aug 4
CA $124
CA $134 total
Aug 3 - Aug 4
includes taxes & fees
6.8/10 (1,199 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 Jul. 16, 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 CA $166 per night from Aug 17 to Aug 18
CA $166
CA $239 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (736 reviews)
"Loved everything!!!"

Reviewed on Jul. 13, 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 CA $162 per night from Aug 10 to Aug 11
CA $162
CA $176 total
Aug 10 - Aug 11
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Nice place"

Reviewed on Jul. 18, 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Ossipee vacation package cost?
You'll find cheap prices from CA $790 on Expedia for your Ossipee getaway. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Ossipee costs.
What are the cheapest months to go to Ossipee?
The off-season is the best time to travel to Ossipee if you're trying to save. Another tip for scoring cheap Ossipee vacation packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Ossipee?
For an Ossipee vacation, a handful of days will be enough to tour the best spots. Make sure to stop by Wentworth State Park — it's one of the top sights in this destination. If you want more activities, consider basing yourself here and going on some tours from Ossipee.
How to find the best Ossipee package deals?
Bagging a cheap Ossipee package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most affordable Ossipee package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Ossipee vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and stays separately. Better still, you can customize your Ossipee trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Ossipee?
If you have your Ossipee vacation dates confirmed, book as early as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Ossipee?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Ossipee.
  2. Work out your budget: Ensure you have enough money to pay for everything from food and transportation to airfares and activities. Your hotel will likely be the largest expense during your trip to Ossipee.
  3. Decide your trip length: Consider how much time you want to spend discovering Ossipee. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find an Ossipee vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.