Ossipee Vacations from $524

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Your Ossipee Vacation

When a city stay is calling your name, answer it with a Ossipee vacation package. With all your travel needs worked out before you leave, all you need to do here is concentrate on enjoying yourself. Can't wait to do some sightseeing but not sure where to start? Every trip to Ossipee should include Elon University. No matter your travel plans or budget, organizing your ultimate tailored Ossipee vacation is a cinch with Expedia.

The Latest Ossipee vacation packages

Price found within the past 48 hours. Click for updated prices.
StudioRes by Marriott Greensboro Airport

StudioRes by Marriott Greensboro Airport

3 out of 5
Price was $739, price is now $524 per person
$524
per person
Jan 13 - Jan 18
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)
9.2/10 Wonderful! (80 reviews)
The hotel is fairly new so the property is well kept. The entire staff I came in contact with was very helpful and attentive. Location is ideal, walking distance to a Top Golf and entertainment facility for kids and adults in the evening and very close to the highway. My only one complaint is that the hotel does not provide a pot or pan for cooking on the electric range. I was there for a little over a week and that would've been very helpful. I did appreciate the microwave and apartment size fridge. Overall, lovely property and I would stay there again.

Reviewed on Nov 4, 2026

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $1,191, price is now $877 per person
$877
per person
Jan 13 - Jan 18
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)
9.8/10 Exceptional! (1,000 reviews)

O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $1,272, price is now $968 per person
$968
per person
Jan 13 - Jan 18
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)
9.8/10 Exceptional! (879 reviews)
We absolutely love staying here!!! We feel very pampered!!! Everything here is amazing!! The beds, service, food, room, showers are excellent!!

Reviewed on Nov 3, 2026

Pandora's Manor Bed & Breakfast

Pandora's Manor Bed & Breakfast

3.5 out of 5
West High Avenue Historic District
Price was $1,343, price is now $1,075 per person
$1,075
per person
Dec 11 - Dec 14
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Greensboro (GSO)
10/10 Exceptional! (2 reviews)
Thanks for a wonderful stay. The property is beautiful and well kept. I was able to get some peace and quiet while attending GHOE and checking on the remodeling of one of my rental properties. I got the best rest during my stay. The property is safe and secure. The staff was very attentive and friendly. Definitely a home away from home. Will stay again.

Reviewed on Nov 1, 2026

The Historic Magnolia House

The Historic Magnolia House

3.5 out of 5
Price was $1,193, price is now $994 per person
$994
per person
Jan 13 - Jan 18
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)
7.4/10 Good! (3 reviews)

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Ossipee Hotel Deals

Hotel Denim

Hotel Denim

3.5 out of 5
1517 Westover Terrace Greensboro NC
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $111 total per night from Nov 15 to Nov 16
$111 total
Nov 15 - Nov 16
Total with taxes and fees
9.2/10 Wonderful! (1,440 reviews)
"The room was cute. The shower nice. The music from the entrance/bar very loud. I could not fall asleep until late. The room was ok clean. Parking was easy."

Reviewed on Nov 4, 2026

Hotel Denim
Marriott Greensboro Downtown

Marriott Greensboro Downtown

4 out of 5
304 North Greene Street Greensboro NC
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $191 total per night from Nov 26 to Nov 27
$191 total
Nov 26 - Nov 27
Total with taxes and fees
Marriott Greensboro Downtown
Drury Inn & Suites Burlington

Drury Inn & Suites Burlington

3 out of 5
1767 Glidewell Drive Burlington NC
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $121 total per night from Dec 6 to Dec 7
$121 total
Dec 6 - Dec 7
Total with taxes and fees
9.6/10 Exceptional! (1,003 reviews)
"Great food, drinks, clean room. Staff friendly"

Reviewed on Nov 4, 2026

Drury Inn & Suites Burlington
See all 492 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.

Find the Best Ossipee Vacation Packages

Ossipee Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Piedmont Triad Intl. Airport (GSO)
Population
560

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Frequently asked questions

How much does an Ossipee vacation package cost?
You can grab a vacation package to this popular destination from $524 on Expedia. But how much your vacation 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?
If you're hoping to score a cheap Ossipee vacation package, consider planning a trip in September, November and December. You'll generally find better prices on flights and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Ossipee?
With a well-planned itinerary, you can easily hit the top Ossipee sights in a few days. But if you'd like to venture off the beaten track or take day trips, consider booking your Ossipee vacation for longer.
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 vacation package as soon as possible.
Is it cheaper to book an Ossipee vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations individually. Better still, you can customize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Ossipee vacation packages?
Your Ossipee break should be an escape from your daily routine, not a source of money-related stress. So to give you extra flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.