Cheap flights from MSN to HHH (Dane County Regional to Hilton Head Island)

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Cheap Flights from MSN to HHH starting at $285 One Way, Round Trip

Prices starting at for return flights and $285 for one-way flights to Hilton Head Island were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Hotel Ideas near Hilton Head Island

Airport Hotels near Hilton Head Island

Hampton Inn Hilton Head

Hampton Inn Hilton Head

2.5 out of 5
1 Dillon Road Hilton Head Island SC
$118 nightly
The price is $130 total per night from Sep 13 to Sep 14
$130 total
Sep 13 - Sep 14
Total with taxes and fees
Book a stay at this golf hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (1,002 reviews)
"Sheets were stained & smelled like smoke. Bathroom floor had hairs all over it. People were yelling in the hallways in the middle of the night."

Reviewed on Aug 29, 2026

Hampton Inn Hilton Head
The Westin Hilton Head Island Resort & Spa

The Westin Hilton Head Island Resort & Spa

4 out of 5
2 Grasslawn Ave Hilton Head Island SC
$266 nightly
The price is $292 total per night from Sep 23 to Sep 24
$292 total
Sep 23 - Sep 24
Total with taxes and fees
Book a stay at this beach hotel in Hilton Head Island. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful ...
8.6/10 Excellent! (1,002 reviews)
"The room requested was with a balcony and chairs. The chairs were wet and the top of the balcony was rotted on the verge of collapse"

Reviewed on Aug 27, 2026

The Westin Hilton Head Island Resort & Spa
Island Links Resort by Palmera

Island Links Resort by Palmera

3 out of 5
1 Coggins Point Road Hilton Head Island SC
Book a stay at this golf aparthotel in Hilton Head Island. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (372 reviews)
"Everything and everybody was great!"

Reviewed on Aug 23, 2026

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Island Links Resort by Palmera
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.

Hotels In Hilton Head Island

Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive Hilton Head Island SC
$288 nightly
The price is $317 total per night from Sep 7 to Sep 8
$317 total
Sep 7 - Sep 8
Total with taxes and fees
Book a stay at this beach resort in Hilton Head Island. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the pool and the helpful ...
Sonesta Resort Hilton Head Island
Hilton Beachfront Resort & Spa Hilton Head Island

Hilton Beachfront Resort & Spa Hilton Head Island

4.5 out of 5
1 Hotel Circle Hilton Head Island SC
$250 nightly
The price is $275 total per night from Sep 7 to Sep 8
$275 total
Sep 7 - Sep 8
Total with taxes and fees
Book a stay at this luxury resort in Hilton Head Island. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful ...
Hilton Beachfront Resort & Spa Hilton Head Island
The Westin Hilton Head Island Resort & Spa

The Westin Hilton Head Island Resort & Spa

4 out of 5
2 Grasslawn Ave Hilton Head Island SC
$266 nightly
The price is $292 total per night from Sep 23 to Sep 24
$292 total
Sep 23 - Sep 24
Total with taxes and fees
Book a stay at this beach hotel in Hilton Head Island. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful ...
8.6/10 Excellent! (1,002 reviews)
"The room requested was with a balcony and chairs. The chairs were wet and the top of the balcony was rotted on the verge of collapse"

Reviewed on Aug 27, 2026

The Westin Hilton Head Island Resort & Spa
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.

Hilton Head Island Hotels With Airport Transportation

Hilton Head Health - Weight Loss Resort and Health Spa

Hilton Head Health - Weight Loss Resort and Health Spa

4 out of 5
14 Valencia Road Hilton Head Island SC
Book a stay at this beach hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Coligny Beach and Shipyard Beach ...
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Hilton Head Health - Weight Loss Resort and Health Spa
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.

Low Priced Hilton Head Island Hotels

Red Roof Inn Hilton Head Island

Red Roof Inn Hilton Head Island

2 out of 5
5 Regency Pkwy Hilton Head Island SC
$71 nightly
The price is $78 total per night from Sep 1 to Sep 2
$78 total
Sep 1 - Sep 2
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions ...
Red Roof Inn Hilton Head Island
Palmera Inn and Suites

Palmera Inn and Suites

3 out of 5
12 Park Ln Hilton Head Island SC
$109 nightly
The price is $117 total per night from Sep 1 to Sep 2
$117 total
Sep 1 - Sep 2
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free breakfast, an outdoor pool, and a fitness center. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,436 reviews)
"We enjoyed the full kitchen & the loft space with an upstairs bathroom."

Reviewed on Aug 29, 2026

Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$77 nightly
The price is $85 total per night from Aug 30 to Aug 31
$85 total
Aug 30 - Aug 31
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (153 reviews)
"Staff were very prompt and courteous. 2 rooms we saw had an overwhelming smell of mildew. The first had what appeared to be mold on the ceiling, and it was just terrible. The second had a construction dumpster outside of the door with a car of tweakers doing tweaker things in it. It also had a 4" ..."

Reviewed on Aug 28, 2026

Hotel Carolina
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.

Family Friendly Hotels in Hilton Head Island

Omni Hilton Head Oceanfront Resort

Omni Hilton Head Oceanfront Resort

4 out of 5
23 Ocean Lane Hilton Head Island SC
$352 nightly
The price is $381 total per night from Sep 9 to Sep 10
$381 total
Sep 9 - Sep 10
Total with taxes and fees
Book a stay at this beach resort in Hilton Head Island. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the bar in our reviews. ...
Omni Hilton Head Oceanfront Resort
Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive Hilton Head Island SC
$288 nightly
The price is $317 total per night from Sep 7 to Sep 8
$317 total
Sep 7 - Sep 8
Total with taxes and fees
Book a stay at this beach resort in Hilton Head Island. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the pool and the helpful ...
Sonesta Resort Hilton Head Island
Hilton Head Island Beach & Tennis Resort

Hilton Head Island Beach & Tennis Resort

3.5 out of 5
40 Folly Field Rd Hilton Head Island SC
Book a stay at this beach hotel in Hilton Head Island. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Popular attractions Coligny Beach and Folly Field ...
7.8/10 Good! (1,000 reviews)

Families like: Outdoor pools, kitchen, playground, on the beach

Travelers say...
"This is our second time staying at Hilton Head Island Beach & Tennis Resort. We love the proximity to the beach. An easy, few minute walk and you’re on the sand! The beach was perfect. Not too crowded and seceral lifeguards present. Multiple pools is a great option. The smaller pool was next to our ..."

Reviewed on Aug 9, 2026

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Hilton Head Island Beach & Tennis Resort
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.

MSN to HHH Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date

Frequently asked questions

Are there non-stop flights from MSN to Hilton Head Airport?
While you can't fly nonstop from Dane County Regional Airport (MSN) to Hilton Head Island Airport (HHH) at the moment, there are plenty of air carriers that operate on this route with just one stop. Why not see if the dates and times offered by American Airlines or United Airlines work with your travel plans? If they don't, take a look at Delta Air Lines.
What is the shortest flight from Dane County Regional Airport (MSN) to HHH?
The shortest flight time from Madison to Hilton Head Island is around 3 hours and 33 minutes. Order your favorite wine from the cabin crew, get stuck into your travel journal or get to know your neighbors — you'll have enough time on this medium-haul trip.
How many hours flight from Truax Field to Hilton Head Airport?
On average, flying from Truax Field to HHH takes 3 hours and 34 minutes. If your aim is to be as comfy as possible, contemplate upgrading your seat using miles or cash.
What airlines have the most flights from Truax Field to HHH?
Watch the planes take off and land, grab a quick meal, chat with a stranger ... Airport stopovers aren't all that bad! If you're traveling between Madison and Hilton Head Island, you won't find any direct flights. Get ready to make a stop somewhere.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.