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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,931, price is now CA $816 per person
CA $816
per person
Dec 18 - Dec 23
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was CA $2,512, price is now CA $1,380 per person
CA $1,380
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was CA $1,647, price is now CA $1,034 per person
CA $1,034
per person
Dec 11 - Dec 13
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $2,646, price is now CA $1,736 per person
CA $1,736
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (1,354 reviews)
The Fairmont Gold level is the best I’ve ever experienced. From the way on line booking to the upgrade section, it was seamless. At check in, Kevin, got my room ready even though I was 6 hours early. Later that day, Kadija was accommodating to my request without any hesitation.

Reviewed on Oct 27, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,031, price is now CA $1,374 per person
CA $1,374
per person
Dec 29 - Jan 2
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
Excellent experience

Reviewed on Oct 22, 2026

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Ossipee Hotel Deals

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 CA $106 per night from Nov 19 to Nov 20
CA $106
CA $115 total
Nov 19 - Nov 20
includes taxes & fees
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 CA $224 per night from Nov 1 to Nov 2
CA $224
CA $303 total
Nov 1 - Nov 2
includes taxes & fees
8.4/10 Very good! (1,009 reviews)
"Beautiful place and location. Enjoyed dinner at two different restaurants on the property and both were delicious. Loved the path and boardwalk with the sculptures through the property and along the waterfront. Very clean room and nice views out the window."

Reviewed on Oct 28, 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 CA $142 per night from Nov 4 to Nov 5
CA $142
CA $154 total
Nov 4 - Nov 5
includes taxes & fees
Best Western Plus Landmark Inn
See all 2,082 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

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 vacation package cost?
You'll find cheap prices from CA $816 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.