Freeport Vacations from $260

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The Latest Freeport vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Medina

Hampton Inn Medina

2.5 out of 5
Price was $347, price is now $260 per person
$260
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Akron (CAK)
8.8/10 Excellent! (992 reviews)
The staff were all amazing- every individual, I encountered was courteous and helpful and showed great pride in their work. David, you rock! The hot savory breakfast choices could be more healthier. The room carpeting can use a cleaning (shampooing, not just vacuuming, to wash away some of the embedded foot/body odor that lingers in the room). Bedding and towels all perfect.

Reviewed on Sep 27, 2025

Bertram Inn at Glenmoor

Bertram Inn at Glenmoor

3.5 out of 5
Save 100% on your flight
Price was $503, price is now $288 per person
$288
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Akron (CAK)
8.6/10 Excellent! (293 reviews)
The room was spacious, quiet, and strange - one window had drapes that didn't open, letting in no outside light. There was an AC unit inside the room with a large hose connected to a window.

Reviewed on Oct 12, 2025

Hilton Garden Inn Akron Canton Airport

Hilton Garden Inn Akron Canton Airport

3 out of 5
Price was $373, price is now $276 per person
$276
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Akron (CAK)
9.2/10 Wonderful! (1,015 reviews)
Always reliably clean, bright and pleasant.

Reviewed on Oct 20, 2025

The Bertram Inn & Conf Ctr Trademark Collection by Wyndham

The Bertram Inn & Conf Ctr Trademark Collection by Wyndham

3.5 out of 5
Save 100% on your flight
Price was $519, price is now $395 per person
$395
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Akron (CAK)
7.6/10 Good! (193 reviews)
Property is very nice, rooms are clean but rather dated. Bathtub was very slippery, wife slipped and would have hit her head on the tub if not for the shower curtain.

Reviewed on Oct 6, 2025

Fairfield Inn & Suites by Marriott Cleveland Streetsboro

Fairfield Inn & Suites by Marriott Cleveland Streetsboro

2.5 out of 5
Price was $358, price is now $295 per person
$295
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Akron (CAK)
8.8/10 Excellent! (695 reviews)
Nice and quiet place. Room is clean and staffs were friendly and nice. Overall, good place to stay.

Reviewed on Oct 20, 2025

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Freeport Hotel Deals

Adventurous Vacation Getaway at the Possum Lodge Cabin!

Adventurous Vacation Getaway at the Possum Lodge Cabin!

Freeport
10/10 Exceptional! (2 reviews)
Birthday get away with the family
Beautiful cabin, with great back deck to hang out on, and lots of land to hike

Reviewed on Apr 27, 2025

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Adventurous Vacation Getaway at the Possum Lodge Cabin!
Beautiful Private Lakefront Cottage with Hot tub

Beautiful Private Lakefront Cottage with Hot tub

Freeport
10/10 Exceptional! (81 reviews)
The property was beautiful and a perfect place to get away from the world and relax. The host had great communication about any questions we had and was very kind. Everything was incredibly clean. Overall I would absolutely recommend this property to anybody who needs a great place to ...

Reviewed on Sep 27, 2025

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Beautiful Private Lakefront Cottage with Hot tub
Red Hill Farm's Newly Renovated "Bunkhouse" with Hot tub and Gameroom

Red Hill Farm's Newly Renovated "Bunkhouse" with Hot tub and Gameroom

2 out of 5
Freeport
10/10 Exceptional! (30 reviews)
Beautiful peaceful bucolic property.

Reviewed on Sep 15, 2025

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Red Hill Farm's Newly Renovated "Bunkhouse" with Hot tub and Gameroom
See all 217 properties in Freeport
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 Freeport Vacation Packages

Freeport Essential Information

Language
English
Currency
U.S dollars
Population
370

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Frequently asked questions

How much does a Freeport vacation package cost?
You can snap up a vacation package to this top destination from $260 on Expedia. However, how much your vacation to Freeport costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Freeport?
You can usually find lower prices and better availability in January, April and November. Browse our cheap Freeport vacation packages and you could land some great off-season deals.
How many days is enough for Freeport?
With a well-organized itinerary, you can easily hit the top Freeport sights in a handful of days. But if you prefer to venture off the beaten track or go on day tours, think about booking your Freeport vacation for longer.
How to find the best Freeport package deals?
Start your search for a Freeport package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Freeport package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Freeport escape off to a flying start.
Is it cheaper to book a Freeport vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still get the flexibility to create a customized Freeport vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Freeport?
If you've got your Freeport vacation dates finalized, book early to snap up some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Freeport vacation packages?
Jet off on your perfect trip to Freeport with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next paycheck — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.