Ossipee Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Ossipee

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 3.177.908 ₫ per night from 31 Aug to 1 Sept
3.177.908 ₫
3.444.073 ₫ total
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (239 reviews)
"This hotel is so cute. The pool was totally clean and warm, which is a rarity for me at hotels. The staff was nice and it's in such a cute area. Most importantly, they were extremely accommodating to my dad's walking issues and gave us a first-floor room right by the front desk. Definitely ..."

Reviewed on 27 Aug 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 2.397.859 ₫ per night from 1 Sept to 2 Sept
2.397.859 ₫
2.614.218 ₫ total
1 Sept - 2 Sept
includes taxes & fees
Country Inn Deerwood
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 2.585.229 ₫ per night from 1 Sept to 2 Sept
2.585.229 ₫
3.095.423 ₫ total
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"The toilet seat was needing adjustment. Beds were noisy when turning over."

Reviewed on 15 Aug 2025

The Lodge at Brainerd Lakes, Trademark Collection by Wyndham
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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday packages? Avoid visiting during public holidays and any major events.
How many days is enough for Ossipee?
With a well-organised travel plan, you can easily hit the most popular Ossipee sights in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Ossipee holiday for longer.
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 holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and accommodation separately. Better still, you can personalise 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 holiday 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 accommodation 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 holiday. 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 holiday package.