Ossipee Vacations

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Find the Best Ossipee Vacation Packages

Ossipee Hotel Deals

The Lodge at Brainerd Lakes, Trademark Collection by Wyndham
The Lodge at Brainerd Lakes, Trademark Collection by Wyndham
3 out of 5
6967 Lake Forest Rd, Brainerd, MN
Fully refundableReserve now, pay when you stay
The price is SAR 402 per night from Jun 8 to Jun 9
SAR 402
SAR 481 total
8 Jun - 9 Jun
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Such a nice, comfortable place to stay, has the feel of a lodge with the decor. Rooms are spacious and beds very comfortable. I would definitely stay here again. Free hot breakfast wh8ch was good. Hostess could have been a bit more welcoming. Basically she ignored me, but that was fine."

Reviewed on 3 June 2025

The Lodge at Brainerd Lakes, Trademark Collection by Wyndham
Pine Peaks Lodge & Suites
Pine Peaks Lodge & Suites
2.5 out of 5
14047 Swann Dr, Crosslake, MN
Fully refundableReserve now, pay when you stay
The price is SAR 452 per night from Jun 8 to Jun 9
SAR 452
SAR 490 total
8 Jun - 9 Jun
includes taxes & fees
9/10 Wonderful! (151 reviews)
"checking in was very easy and the room was very clean"

Reviewed on 4 June 2025

Pine Peaks Lodge & Suites
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 SAR 324 per night from Jun 10 to Jun 11
SAR 324
SAR 354 total
10 Jun - 11 Jun
includes taxes & fees
7/10 Good! (957 reviews)
"The hot tub wasn’t working"

Reviewed on 30 May 2025

Country Inn Deerwood
See all 912 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 vacation package cost?
Offering excellent value package deals on Expedia, you’ll be thrilled with how little a vacation to Ossipee costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Ossipee?
The off-season is the best time to head to Ossipee if you’re trying to save. Another tip for scoring cheap Ossipee vacation packages? Avoid visiting during public holidays and any major events.
How to find the best Ossipee package deals?
Start your search for an Ossipee package deal by entering your preferred travel dates and destination under our “Packages” tab. Then apply some filters, like “Popular locations” and “Amenities,” to fine-tune the results to your exact style. You can also sort by “Package discount” and discover offers that come with huge savings. If you don’t find the ideal Ossipee package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Ossipee getaway off to a flying start.
Is it cheaper to book an Ossipee vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations separately. Better still, you can personalize your Ossipee escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Ossipee?
Secure incredible discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Ossipee adventure.
How to plan a trip to Ossipee?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Ossipee.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to activities and airfares. Your accommodations will likely be the largest expense during your trip to Ossipee.
  3. Decide how long to go away for: Now that you’re up to speed on Ossipee, you can work out the perfect length of your vacation. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored Ossipee vacation package.