Diamondhead Vacations from $395

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Your Diamondhead Vacation

When a city escape is calling, answer it with a Diamondhead vacation package. With all your travel arrangements in place before you go, all you have to do here is concentrate on having fun. Eager to explore? Hollywood Casino, Diamondhead Country Club and Hancock County Sports Complex are just three of the top-rated places to visit during your trip to Diamondhead. Browse Expedia's wide range of travel options and book your dream vacation to Diamondhead now.

The Latest Diamondhead vacation packages

Price found within the past 48 hours. Click for updated prices.
Centennial Plaza Resort Gulfport

Centennial Plaza Resort Gulfport

$395
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Gulfport (GPT)
9/10 Wonderful! (1,008 reviews)
Landing Furnished Apartments Ocean Springs - Gulf Hills

Landing Furnished Apartments Ocean Springs - Gulf Hills

$531
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Gulfport (GPT)
10/10 Exceptional! (1 review)
Best than I could’ve ever expected.

Reviewed on Jul 11, 2026

Gulf Hills Hotel & Resort

Gulf Hills Hotel & Resort

$527
per person
Oct 26 - Oct 31
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Gulfport (GPT)
9/10 Wonderful! (848 reviews)
The hotel was absolutely beautiful and staff extremely helpful!!! However, the faucet in bath did not work but I made do but everything else was PERFECT and I will be returning for future stays, the Vibe and decor is perfection!!

Reviewed on Aug 16, 2026

Gil's Bayou Cabins

Gil's Bayou Cabins

$552
per person
Oct 26 - Oct 31
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Gulfport (GPT)
10/10 Exceptional! (17 reviews)
The cabin is located with easy access to downtown ocean springs and the bridge. It is located with a nice view of the water. There are frequent trains that go through, but they did not bother us at night. It stayed very cool with AC and ceiling fans. Bring a sleep mask of light bothers you because the temperature light on the AC unit lights up the entire cabin. There is no storage to hang clothes or bags so we had to pile everything on the couch which made it feel cluttered. There was no iron or ironing board and we did go out for a nice dinner, so it was not great to be wrinkled. There is a small fridge and basic kitchen supplies. Hot water in the shower, but the pressure was that of a pressure washer so beware. At least there was pressure. One trick I’ll provide. Your gps will want you to turn onto Washington Ave, go over the bridge, turn around, and come back (if you’re leaving the parking lot and want to turn left). Instead, right before you’d get out onto Washington Ave, go right into the parking lot at Gil’s. You’ll see that you can drive under the bridge and pop out the other side. It will save a lot of time! Overall it was a great place to crash, but a little inconvenient to get in and out of and lack of storage was a bit annoying.

Reviewed on Aug 16, 2026

The Downtown Cedar

The Downtown Cedar

$827
per person
Oct 26 - Oct 31
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Gulfport (GPT)
9/10 Wonderful! (2 reviews)
Nice little home that’s located close to downtown. It was great for what we needed. It is not handicapped friendly, tho. Currently (May 2026), there is a high 1-step front door entry that could be easily fixed with a sturdy second platform step up from the nice front porch to make it easier to get in and out. It also has a nice upgraded single bathroom, but the claw tub is deep without a handrail and no suction in-tub bath mat to keep a person from falling. The rain shower is great however. Kitchen has good amenities, and the dining and living room areas are nice. Good amount of seating, large TV. Overall, for an older home, it’s nice and, a big plus, it doesn’t have a musty smell.

Reviewed on Jun 3, 2026

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Stay near popular Diamondhead attractions

Diamondhead Country Club

8.0/10 (44 reviews)
Enjoy a round of golf in Diamondhead at Diamondhead Country Club. Stroll along the beautiful beaches in this relaxing area, or check out its top-notch restaurants.
See properties

Diamondhead Hotel Deals

Ramada by Wyndham Diamondhead I-10/Gulfport

Ramada by Wyndham Diamondhead I-10/Gulfport

103 Live Oak Drive Diamondhead MS
Fully refundableReserve now, pay when you stay
$70 nightly
$76 total
Aug 25 - Aug 26
Total with taxes and fees
Ramada by Wyndham Diamondhead I-10/Gulfport
Econo Lodge Inn & Suites Diamondhead

Econo Lodge Inn & Suites Diamondhead

441 Yacht Club Dr Diamondhead MS
Fully refundable
$71 nightly
$78 total
Aug 30 - Aug 31
Total with taxes and fees
Econo Lodge Inn & Suites Diamondhead
Centennial Plaza Resort Gulfport

Centennial Plaza Resort Gulfport

200 E. Beach Blvd Gulfport MS
Fully refundableReserve now, pay when you stay
$144 nightly
$159 total
Sep 2 - Sep 3
Total with taxes and fees
Centennial Plaza Resort Gulfport
See all 1,393 properties in Diamondhead
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 Diamondhead Vacation Packages

Diamondhead Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Gulfport - Biloxi Intl. Airport (GPT)
Population
8,100
Max Temp Winter
60ºF
Max Temp Summer
90ºF
Top Sights
Buccaneer Bay Waterpark, Buccaneer State Park and Bay St. Louis Little Theater

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Frequently asked questions

How much does a Diamondhead vacation package cost?
You'll find cheap prices from $395 on Expedia for your Diamondhead break. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Diamondhead costs.
What are the cheapest months to go to Diamondhead?
You can usually find reduced prices and better availability in January, August and September. Explore our cheap Diamondhead vacation packages and you could land some great off-season deals.
How many days is enough for Diamondhead?
The ideal length for your Diamondhead vacation depends on what you'd like to see and do. Generally, a few days to a week will give you enough time to hit all the leading sights and explore some hidden gems along the way.
How to find the best Diamondhead package deals?
Begin your search for a Diamondhead package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Diamondhead package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Diamondhead escape underway.
Is it cheaper to book a Diamondhead vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Diamondhead vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Diamondhead?
If you're considering a spur-of-the-moment Diamondhead getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Diamondhead vacation packages?
Your Diamondhead break is meant to be a relaxing escape from your daily routine, not a source of money worries. So to give you a bit more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.