Ossipee Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Ossipee Vacation Packages

Ossipee Hotel Deals

Newly Remodeled Lakefront Cabin w/ Hot Tub & Private Dock

Newly Remodeled Lakefront Cabin w/ Hot Tub & Private Dock

Merrifield MN
10/10 Exceptional! (3 reviews)
"Amazing property!"

Reviewed on 14 July 2026

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Newly Remodeled Lakefront Cabin w/ Hot Tub & Private Dock
*HIGH DEMAND* Sugar Sand Beach & Cozy Cabin That Sleeps 10 on Pelican Lake!

*HIGH DEMAND* Sugar Sand Beach & Cozy Cabin That Sleeps 10 on Pelican Lake!

Merrifield MN
9.8/10 Exceptional! (76 reviews)
"Great place to stay. Great beach!"

Reviewed on 5 July 2026

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*HIGH DEMAND* Sugar Sand Beach & Cozy Cabin That Sleeps 10 on Pelican Lake!
Country Inn Deerwood

Country Inn Deerwood

2.5 out of 5
23884 Front Street Deerwood MN
Fully refundableReserve now, pay when you stay
The price is SARĀ 285 per night from Jul 26 to Jul 27
SARĀ 285
SARĀ 312 total
26 Jul - 27 Jul
includes taxes & fees
6.8/10 (1,009 reviews)
"Room 105 stunk. We got room 103 instead. A bit better but still smelled bad. Shower curtain showed mold stain. Ceiling had water stain. Not sure if that was mold or anything else. Coffee pot not working. Hot tub out of commission. Breakfast was so small. Coffee was cold. A pancake machine but no ..."

Reviewed on 20 July 2026

Country Inn Deerwood
See all 974 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.

Stay near popular Ossipee attractions

Upper Mission Lake

Commune with nature and explore the great outdoors at Upper Mission Lake during your travels in Ossipee. Wander the lakeside and beaches while you're in the area.
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Frequently asked questions

How much does an Ossipee vacation package cost?
You'll find cheap prices on Expedia for your Ossipee break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Ossipee costs.
What are the cheapest months to go to Ossipee?
Plan your getaway for the off-season and you're likely to score cheap Ossipee vacation packages. Bear in mind that school vacation periods and local events and festivals can impact prices, so do your research before you go.
How to find the best Ossipee package deals?
Finding a cheap Ossipee package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" 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? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Ossipee vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights individually. Better still, you can customize your Ossipee getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Ossipee?
If you're considering a spontaneous Ossipee vacation, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Ossipee?

  1. Choose when to go: Check your calendar and get packing. Your preferred season and the type of activities on offer will also help you decide when to visit Ossipee.
  2. Plan your budget wisely: Besides the price of your stay, you'll need to consider other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that may arise during your trip to Ossipee.
  3. Decide how long to go away for: Now that you know more about Ossipee, you can figure out the perfect length of your vacation. Pull together a draft plan and give yourself enough time for all the things you want to do.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick an Ossipee vacation package that brings all your bookings together.