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 $240 One Way, $253 Round Trip

Prices starting at $253 for return flights and $240 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.

Fri, Aug 8 - Mon, Aug 18
MSN
Madison
HHH
Hilton Head Island
$253 Roundtrip, found 6 days ago
$253
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Aug 8 from Madison to Hilton Head Island, returning Mon, Aug 18, priced at $253 found 6 days ago
Tue, Aug 5 - Tue, Aug 26
MSN
Madison
HHH
Hilton Head Island
$299 Roundtrip, found 6 days ago
$299
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 5 from Madison to Hilton Head Island, returning Tue, Aug 26, priced at $299 found 6 days ago
Tue, Aug 5 - Wed, Aug 6
MSN
Madison
HHH
Hilton Head Island
$316 Roundtrip, found 6 days ago
$316
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 5 from Madison to Hilton Head Island, returning Wed, Aug 6, priced at $316 found 6 days ago
Wed, Aug 6 - Wed, Aug 13
MSN
Madison
HHH
Hilton Head Island
$335 Roundtrip, found 6 days ago
$335
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Aug 6 from Madison to Hilton Head Island, returning Wed, Aug 13, priced at $335 found 6 days ago
Tue, Aug 5 - Thu, Aug 14
MSN
Madison
HHH
Hilton Head Island
$344 Roundtrip, found 6 days ago
$344
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 5 from Madison to Hilton Head Island, returning Thu, Aug 14, priced at $344 found 6 days ago

Hotel Ideas near Hilton Head Island

Airport Hotels near 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
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 ...
8.4/10 Very Good! (1,004 reviews)
"The resort was beautiful! We loved our room, the pools, and restaurants! My only complaints would be the food and early end time for the wedding we attended there."

Reviewed on Jun 22, 2025

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The Westin Hilton Head Island Resort & Spa
Hampton Inn Hilton Head
Hampton Inn Hilton Head
2.5 out of 5
1 Dillon Road, Hilton Head Island, SC
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! (1,004 reviews)
"My room was clean, the staff was friendly and nice, the location was good for us."

Reviewed on Jun 30, 2025

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Hampton Inn Hilton Head
Island Links Resort by Palmera
Island Links Resort by Palmera
3 out of 5
1 Coggins Point Road, Hilton Head Island, SC
Stay at this 3-star golf aparthotel in Hilton Head Island. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (295 reviews)
"Loved the pool. Shuttle service to beach fantastic.Dishwasher wasn't working"

Reviewed on Jun 20, 2025

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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

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
Stay at this 4.5-star luxury resort in Hilton Head Island. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in ...
8.4/10 Very Good! (1,308 reviews)
"Loved idea of a pool & bar with beach within walking. Some bar staff were helpful & personable, while others were not, a couple groups standing together talking therefore not very attentive to their customers. I would recommend better security, we just walked in any door from the outside without ..."

Reviewed on Jun 30, 2025

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Hilton Beachfront Resort & Spa Hilton Head Island
Beach House Resort Hilton Head
Beach House Resort Hilton Head
4 out of 5
1 South Forest Beach Drive, Hilton Head Island, SC
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy free WiFi, a beach locale, and 2 bars/lounges. Our guests praise the restaurant and the bar in our ...
8.8/10 Excellent! (661 reviews)
"Nice hotel, conveniently located to Coligny Plaza with shops and dining. Some rooms are upgraded at this time while others are not. Staff is incredibly kind."

Reviewed on Jul 1, 2025

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Beach House Resort Hilton Head
Sonesta Resort Hilton Head Island
Sonesta Resort Hilton Head Island
4 out of 5
130 Shipyard Drive, Hilton Head Island, SC
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy a full-service spa, a beach locale, and breakfast (surcharge). Our guests praise the pool and the ...
8.4/10 Very Good! (1,013 reviews)
"This was the 2nd time that I stayed here and it was awesome."

Reviewed on Jul 1, 2025

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Sonesta Resort Hilton Head Island
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
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Coligny Plaza and Coligny 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, Us 278, 30 Miles From I-95, Hilton Head Island, SC
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 ...
6.2/10 (1,000 reviews)
"Liked the privacy and convenience"

Reviewed on Jun 28, 2025

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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
Stay at this 3-star hotel in Hilton Head Island. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,046 reviews)
"Very clean, good proximity."

Reviewed on Jul 1, 2025

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Palmera Inn and Suites
Hotel Carolina, a Days Inn by Wyndham
Hotel Carolina, a Days Inn by Wyndham
2 out of 5
9 Marina Side Drive, Hilton Head Island, SC
Book a stay at this business-friendly hotel in Hilton Head Island. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and ...
6.4/10 (1,009 reviews)
"Our stay was nice. We enjoyed the convenience and location. Everything was as described."

Reviewed on Jun 29, 2025

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Hotel Carolina, a Days Inn by Wyndham
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
Stay at this 4-star 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. ...
8.8/10 Excellent! (1,000 reviews)

Families like: Outdoor pools, kids club, kitchenette, playground

Travelers say...
"This is a great option for a resort type feel! They keep this property clean and service is amazing! While there are families with young children, it was still very quiet. I am single and traveled alone. I was able to relax and enjoy my stay. I was impressed with everything they offered! Most restaurants ..."

Reviewed on Jun 29, 2025

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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
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy a full-service spa, a beach locale, and breakfast (surcharge). Our guests praise the pool and the ...
8.4/10 Very Good! (1,013 reviews)

Families like: Outdoor pool, kids club, on the beach, bicycle rentals

Travelers say...
"This was the 2nd time that I stayed here and it was awesome."

Reviewed on Jul 1, 2025

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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
Stay at this 3.5-star beach hotel in Hilton Head Island. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Popular attractions Palmetto Dunes Club and Coligny ...
7.6/10 Good! (1,005 reviews)

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

Hilton Head island Beach and Tennis Resort
"Bathroom had no safety bars in tub and needed better lighting. No towel service other than beginning of visit. Had to pay extra $$$ to get second delivery of towels. No towels provided at pool. No paper products provided except when we first arrived. Noise from unit above and on outside stairwell. ..."

Reviewed on Jun 30, 2025

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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.