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.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,287, price is now CA $924 per person
CA $924
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (193 reviews)
The location couldn’t have been more perfect and despite it being a holiday weekend the parking lot/BNB never felt crowded. Everyone we encountered was lovely and helpful, and the room was a perfect place to take a midday nap or unwind after hours on the beach! We would definitely stay again.

Reviewed on Jul 6, 2026

The Charles Hotel

The Charles Hotel

5 out of 5
West Cambridge
Price was CA $2,028, price is now CA $1,328 per person
CA $1,328
per person
Aug 12 - Aug 16
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (1,002 reviews)
Great experience but check in was delayed for a while and ended up in a different room category but hotel is beautiful and centrally located.

Reviewed on Jul 5, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,611, price is now CA $2,537 per person
CA $2,537
per person
Sep 17 - Sep 20
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Price was CA $5,480, price is now CA $3,971 per person
CA $3,971
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on Oct 8, 2025

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $3,063, price is now CA $2,240 per person
CA $2,240
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (720 reviews)
Chatham Tides is a slice of heaven. Beautiful location. Clean, well maintained. Staff was super helpful with local restaurants. My wife and I gave it a 11/10

Reviewed on Jul 2, 2026

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Ossipee Hotel Deals

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 $165 per night from Jul 21 to Jul 22
CA $165
CA $179 total
Jul 21 - Jul 22
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"Upon checking with two young children at 11pm was told our reservation was canceled and we needed to call Expedia they offered no help at all even seeing my two children sleeping. We called Expedia to be told nothing was wrong with our reservation so finally front desk gives us room we go to check ..."

Reviewed on Jul 5, 2026

Best Western Plus Landmark Inn
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 $278 per night from Jul 10 to Jul 11
CA $278
CA $363 total
Jul 10 - Jul 11
includes taxes & fees
8.4/10 Very good! (1,005 reviews)
"Beautiful area"

Reviewed on Jul 3, 2026

Mill Falls Resort Collection at the Lake
The Naswa Resort

The Naswa Resort

3 out of 5
1086 Weirs Blvd Laconia NH
The price is CA $328 per night from Aug 5 to Aug 6
CA $328
CA $355 total
Aug 5 - Aug 6
includes taxes & fees
8.6/10 Excellent! (775 reviews)
"Wonderful stay...clean, great staff, fun beach front bar and good food. Highly recommended."

Reviewed on Jul 5, 2026

The Naswa Resort
See all 2,110 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
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Beach Vacations
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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 $924 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.

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