Ossipee Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Ossipee

Hotel Denim
Hotel Denim
3.5 out of 5
1517 Westover Terrace, Greensboro, NC
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (951 reviews)
"This was a very cute and small hotel. Clean and the customer service was wonderful. I would definitely be back."

Reviewed on 28 Jun, 2025

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Hotel Denim
Proximity Hotel
Proximity Hotel
4 out of 5
704 Green Valley Road, Greensboro, NC
Fully refundableReserve now, pay when you stay
9.6/10 Exceptional! (811 reviews)
"Nice lobby. Friendly Staff. Spacious room. Well maintained pool."

Reviewed on 27 Jun, 2025

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Proximity Hotel
Hyatt Place Greensboro/Downtown
Hyatt Place Greensboro/Downtown
3 out of 5
300 N Eugene St, Greensboro, NC
Fully refundableReserve now, pay when you stay
The price is S$258 per night from 1 Jul to 2 Jul
S$258
1 Jul - 2 Jul
includes taxes & fees
8.8/10 Excellent! (912 reviews)
"wonderful room but must say the day bed was unsleepable i snore so i tried to sleep on the day bed in the other part of the room and it had a terrible bar that goes across someone lying there on their higher back.. Had a great view of the ballpark"

Reviewed on 20 Jun, 2025

Hyatt Place Greensboro/Downtown
See all 403 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?
You can grab a holiday package to this popular destination on Expedia. But how much your holiday to Ossipee costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Ossipee?
January, February and June are great times to search for cheap Ossipee holiday packages. Opting to travel in less busy periods means you can typically find lower prices on accommodation and flights.
How many days is enough for Ossipee?
Usually, a handful of days is enough to check out the major sights during your Ossipee holiday. But if you'd like to have more time to chill out or go on day trips, consider extending your itinerary.
How to find the best Ossipee package deals?
Use Expedia's filters to find some unbeatable Ossipee package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Ossipee package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book an Ossipee holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and accommodation individually. Better still, you can customise your Ossipee escape 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 holiday package to Ossipee?
If you have your Ossipee travel dates finalized, book as soon as you can to bag some fantastic deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Ossipee?

  1. Pick your dates: What you plan to do in Ossipee and your favourite season can help you decide when to get away.
  2. Plan your budget wisely: Besides the cost of your stay, you should factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Ossipee.
  3. Decide your trip length: Consider how much time you want to spend exploring Ossipee. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose an Ossipee holiday package that brings all your bookings together.