Headland Vacations from $496

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The Latest Headland vacation packages

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

OYO Hotel Daleville AL Hwy 84

$496

per person

Oct 31 - Nov 4

found 4 hours ago

Roundtrip non-stop flight included

Fort Myers (RSW) to Dothan (DHN)

3.4/10 (101 reviews)

The building is demolished. There is not hotel at this location.

Reviewed on Sep 21, 2026

Ramada by Wyndham Studio Suites Dothan

$537

per person

Oct 31 - Nov 4

found 4 hours ago

Roundtrip non-stop flight included

Fort Myers (RSW) to Dothan (DHN)

8.2/10 Very Good! (264 reviews)

They had roaches in the bathroom.

Reviewed on Sep 30, 2026

Comfort Inn & Suites Dothan Northside Plaza

$599

per person

Oct 31 - Nov 4

found 4 hours ago

Roundtrip non-stop flight included

Fort Myers (RSW) to Dothan (DHN)

6.4/10 (1,001 reviews)

The staff was nice we really enjoyed are stay will definitely recommend this hotel

Reviewed on Sep 29, 2026

Holiday Inn Express & Suites Enterprise by IHG

$633

per person

Oct 31 - Nov 4

found 4 hours ago

Roundtrip non-stop flight included

Fort Myers (RSW) to Dothan (DHN)

8.6/10 Excellent! (427 reviews)

Sleep Inn & Suites Dothan North

$534

per person

Oct 31 - Nov 4

found 4 hours ago

Roundtrip non-stop flight included

Fort Myers (RSW) to Dothan (DHN)

8/10 Very Good! (1,000 reviews)

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Headland Hotel Deals

Downtown Main St Gem -Studio/Loft 5

Headland AL

$150 nightly

$167 total

Oct 26 - Oct 27

Total with taxes and fees

8/10 Very Good! (2 reviews)

"The studio is located in a great spot downtown. Unfortunately, the space in the loft area is not easily accessible for those with mobility issues."

Reviewed on Sep 14, 2026

La Quinta Inn & Suites by Wyndham Dothan

3593 Ross Clark Cir Dothan AL

Fully refundableReserve now, pay when you stay

$79 nightly

$90 total

Nov 1 - Nov 2

Total with taxes and fees

8.4/10 Very Good! (1,160 reviews)

"Always a great stay!"

Reviewed on Sep 30, 2026

Baymont by Wyndham Dothan

2841 Ross Clark Cir Dothan AL

Fully refundableReserve now, pay when you stay

$60 nightly

$68 total

Oct 4 - Oct 5

Total with taxes and fees

See all 235 properties in Headland

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 Headland Vacation Packages

Headland Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Dothan Regional Airport (DHN)
Population	4,700

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Frequently asked questions

How much does a Headland vacation package cost?

You'll find cheap prices from $496 on Expedia for your Headland escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Headland costs.

What are the cheapest months to go to Headland?

You can generally find reduced prices and greater availability in October, November and December. Browse our cheap Headland vacation packages and you could score some great off-season discounts.

How many days is enough for Headland?

Typically, a handful of days is enough to explore the major sights during your Headland vacation. However, if you'd like to have more time to chill out or go on day trips, think about extending your trip.

How to find the best Headland package deals?

Start your search for a Headland package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Headland package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Headland adventure off to a flying start.

Is it cheaper to book a Headland vacation as a package?

You can enjoy significant savings on your next Headland break by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.

When to book a vacation package to Headland?

If you're considering an impromptu Headland trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking ahead.

Does Expedia offer Book Now, Pay Later Headland vacation packages?

If you're anything like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Headland break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

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Things to do in Dothan

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