Diamondhead Vacations from $338

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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.
Gulf Hills Hotel & Resort

Gulf Hills Hotel & Resort

2.5 out of 5
Price was $429, price is now $338 per person
$338
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Gulfport (GPT)
8.8/10 Excellent! (775 reviews)
Property was very clean, staff were very helpful and pleasant. Room was clean, air conditioner and heat were working well. Have stayed here before and will be back.

Reviewed on Jan 3, 2026

Silver Slipper Casino & Hotel - Adults Only

Silver Slipper Casino & Hotel - Adults Only

3.5 out of 5
Price was $487, price is now $374 per person
$374
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Gulfport (GPT)
8.6/10 Excellent! (1,005 reviews)
Very good at catering to their guests.

Reviewed on Dec 16, 2025

Holiday Inn Express Gulfport Beach by IHG

Holiday Inn Express Gulfport Beach by IHG

3 out of 5
Price was $770, price is now $617 per person
$617
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Gulfport (GPT)
9.4/10 Exceptional! (772 reviews)
Wish the pool was heated for colder months, but not a deal breaker for next nee years eve

Reviewed on Jan 7, 2026

Hotel Whiskey in Pass Christian

Hotel Whiskey in Pass Christian

3.5 out of 5
Price was $1,496, price is now $1,268 per person
$1,268
per person
Feb 12 - Feb 16
found 6 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Gulfport (GPT)
9.4/10 Exceptional! (600 reviews)
Great stay! Easy check and check out

Reviewed on Jan 7, 2026

The Springs Hotel

The Springs Hotel

2 out of 5
Price was $543, price is now $461 per person
$461
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Gulfport (GPT)
9.6/10 Exceptional! (111 reviews)
Our stay at the Speings was perfect! The room, amenities and staff are amazing. It was the perfect weekend getaway. Can’t wait to go back to the Springs Hotel.

Reviewed on Oct 31, 2025

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Discover the most popular places to visit in Diamondhead

Diamondhead Country Club

4/5(21 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.

Diamondhead Country Club

Diamondhead Hotel Deals

Ramada by Wyndham Diamondhead I-10/Gulfport

Ramada by Wyndham Diamondhead I-10/Gulfport

2.5 out of 5
103 Live Oak Drive Diamondhead MS
Fully refundableReserve now, pay when you stay
$64 nightly
The price is $70 total per night from Jan 16 to Jan 17
$70 total
Jan 16 - Jan 17
Total with taxes and fees
7.8/10 Good! (581 reviews)
Staff were friendly

Reviewed on Jan 6, 2026

Ramada by Wyndham Diamondhead I-10/Gulfport
Econo Lodge Inn & Suites Diamondhead

Econo Lodge Inn & Suites Diamondhead

2 out of 5
441 Yacht Club Dr Diamondhead MS
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $82 total per night from Jan 17 to Jan 18
$82 total
Jan 17 - Jan 18
Total with taxes and fees
7.2/10 Good! (597 reviews)
Comfortable bed, plenty of hot water, adequate accommodation’s for

Reviewed on Dec 8, 2025

Econo Lodge Inn & Suites Diamondhead
Best Western Seaway Inn

Best Western Seaway Inn

2.5 out of 5
9475 US 49 Gulfport MS
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $83 total per night from Jan 18 to Jan 19
$83 total
Jan 18 - Jan 19
Total with taxes and fees
8.6/10 Excellent! (1,346 reviews)
This was the best free breakfast ever offered at any brand of hotels.

Reviewed on Jan 8, 2026

Best Western Seaway Inn
See all 1,375 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 $338 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.