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Cottages in Hilton Head Island

Find the cottages that appeal to you the most

August 2026

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Cottages for every style

Find the right cottage for you in Hilton Head Island

The best cottages in Hilton Head Island

Check out our selection of great cottages in Hilton Head Island

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Luxury Penthouse near Beach Tiki Hut Coligny

Hilton Head Island

Luxury Penthouse near Beach Tiki Hut Coligny offers accommodations in Hilton Head Island, a 2-minute walk from Coligny Beach Park.

K
Kellie
From
United States
Comfortable beds, good location to Coligny beach
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 8 reviews
Price from
$499.54
1 night, 2 adults
Check availability

Seaside 235

Hilton Head Island

Featuring massage services, Seaside 235 offers accommodations in Hilton Head Island. Both free Wifi and parking on-site are accessible at the vacation home free of charge.

B
Bettyann
From
United States
The location was perfect. close to the beach and restaurants. Nice walk in the morning to the coffee shop. We felt safe enough n the gated community. The unit was well equipped. Loved sitting out on the balcony
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews
Price from
$233.58
1 night, 2 adults
Check availability

Newly Renovated Duplex, Upper Unit, 4th row from the beach

Hilton Head Island

Newly Renovated Duplex, Upper Unit, 4th row from the beach offers accommodations in Hilton Head Island, a 4-minute walk from Folly Field Beach Park.

W
Wiese
From
United States
Great property! Clean and had a nice backyard. Great location. Nice updated kitchen and furniture.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 13 reviews
Price from
$373
1 night, 2 adults
Check availability

Seaside 282

Hilton Head Island

Offering massage services, Seaside 282 features accommodations in Hilton Head Island. Both free Wifi and parking on-site are available at the vacation home free of charge.

R
Regina
From
United States
This condo was perfect for my grounding and writing retreat. It is just a few steps from the ocean. The space was very clean, and it had everything you needed to prepare meals or just relax and feel at home. The complex has ample free parking, an elevator, and conveniently located luggage carts to move in and out. The pool in the complex is well-kept. I have added this listing to my favorites for a Hilton Head getaway!
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews
Price from
$233.58
1 night, 2 adults
Check availability

Serene Hilton Head Island Condo w/ Community Pool!

Hilton Head Island

Serene Hilton Head Island Condo w/ Community Pool! offers accommodations in Hilton Head Island, a 11-minute walk from Hilton Head Island Beach South.

H
Hildamarie
From
United States
The property was exactly like the photos- it was beautifully decorated, the bed was very comfortable and it was close to the beach. It had everything you needed for a wonderful getaway. The coffee bar was awesome and we enjoyed it very much.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 10 reviews
Price from
$366.20
1 night, 2 adults
Check availability

Tranquility in paradise- 2 bedroom villa w/parking

Hilton Head Island

Featuring a garden, Tranquility in paradise- 2 bedroom villa w/parking provides accommodations in Hilton Head Island. This property offers access to a terrace and free private parking.

X
Xiaohua
From
United States
Quiet location, clean and convenient
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 25 reviews
Price from
$333.15
1 night, 2 adults
Check availability

In the Heart of Harbour Town 2BR 2BA Pool Access Close to Beach

Hilton Head Island

Offering a bar, In the Heart of Harbour Town 2BR 2BA Pool Access Close to Beach offers accommodations in Hilton Head Island.

J
Joshua
From
United States
Location could not get any better. Close to shopping and dining and could easily walk to get around. House was adorable and made you feel at home.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 19 reviews
Price from
$369.60
1 night, 2 adults
Check availability

Direct Oceanfront Villa - Heated Pool & Breathtaking Ocean View

Hilton Head Island

Direct Oceanfront Villa - Heated Pool & Breathtaking Ocean View offers accommodations in Hilton Head Island, a 5-minute walk from Hilton Head Island Beach South.

L
Leonard
From
United States
Very well kept and clean. Only a few steps from the beach with ocean front view. Elevator to assist with getting your stuff to the room.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 47 reviews
Price from
$488
1 night, 2 adults
Check availability

Seaside 158

Hilton Head Island

Featuring massage services, Seaside 158 offers accommodations in Hilton Head Island. Both free Wifi and parking on-site are accessible at the vacation home free of charge.

A
Amie
From
United States
Easy access. Great location close to everything! Great decor very clean. Nice little treat left by the owners, that was a nice surprise 😊
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 7 reviews
Price from
$233.58
1 night, 2 adults
Check availability

Seaside 190

Hilton Head Island

Providing massage services, Seaside 190 offers accommodations in Hilton Head Island. Both free Wifi and parking on-site are available at the vacation home free of charge.

A
Amanda
From
United States
The location of the property was perfect. The condo was clean and had all the amenities we needed.
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 8 reviews
Price from
$233.58
1 night, 2 adults
Check availability
All cottages in Hilton Head Island

Looking for a cottage?

Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.

Most booked cottages in Hilton Head Island and surrounding area in the past month

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Popular with guests booking cottages in Hilton Head Island

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking cottages in Hilton Head Island

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

Popular with guests booking cottages in Hilton Head Island

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 11 reviews

Popular with guests booking cottages in Hilton Head Island

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 3 reviews

Popular with guests booking cottages in Hilton Head Island

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 9 reviews

Popular with guests booking cottages in Hilton Head Island

Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 7 reviews

Popular with guests booking cottages in Hilton Head Island

Scored out of 10, guest rating 6.9
Pleasant - What previous guests thought, 8 reviews

Popular with guests booking cottages in Hilton Head Island

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews

Popular with guests booking cottages in Hilton Head Island

Popular with guests booking cottages in Hilton Head Island

Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 16 reviews

Traveling by car? These cottages in Hilton Head Island and nearby offer free parking

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This vacation home features free private parking, a 24-hour front desk, and free Wifi. Outdoor seating is also available at 26 Muirfield Road at The Sea Pines Resort.

This vacation home offers free private parking, a 24-hour front desk, and free Wifi. Outdoor seating is also available at 26 Muirfield Road at The Sea Pines Resort.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Both free Wifi and private parking are available at 5 Mi to Beach: Spacious Home on Hilton Head Island free of charge.

Both free Wifi and parking on-site are available at 240 Olive Shell Court free of charge.

Both free Wifi and parking on-site are available at 200 Olive Shell Court free of charge.

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 3 reviews

Offering free bikes, The Owners Club of Hilton Head features accommodations in Hilton Head Island. A hot tub is available for guests, along with a fitness room.

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 15 reviews

The vacation home, set in a building dating from 2022, offers free Wifi and free private parking.

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 4 reviews

Providing barbecue facilities, 4BD Beach & Golf Retreat! Game Room, Beach Gear offers accommodations in Hilton Head Island. The property features free private parking.

These cottages in Hilton Head Island and nearby have options with free cancellation

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MBR King & 4 Queens Huge Living Room Covered Porch Bikes & Beach Gear included offers accommodations in Hilton Head Island, 5.6 miles from Island Ideas Gallery and 6.1 miles from Art League Of Hilton...

King 2 Queens 3 Doubles Foldout Stainless Steel is located in Hilton Head Island, just 3.9 miles from Pink House Gallery Of Fine Art & Framing and 4.1 miles from Karis Art Gallery.

Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1 review

Both Wifi and private parking are accessible at 4 Mi to Beach: Family-Friendly Hilton Head Retreat free of charge.

This vacation home features air-conditioned accommodations with a patio and free Wifi.

Anchorage 7442

Hilton Head Island
Free cancellation options available

Both free Wifi and parking on-site are accessible at Anchorage 7442 free of charge.

Scored out of 10, guest rating 7.2
Good - What previous guests thought, 6 reviews

Family Beach Stay | Pool | Tennis | Pet Friendly offers accommodations in Hilton Head Island, 1.1 miles from Pink House Gallery Of Fine Art & Framing and 1.4 miles from Ben Ham Images.

240 Captains Quarters

Hilton Head Island
Free cancellation options available

This property offers access to a balcony, free private parking, and free Wifi.

201 Captains Quarters

Hilton Head Island
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Featuring massage services, 201 Captains Quarters provides accommodations in Hilton Head Island. This vacation home features free private parking, an elevator, and free Wifi.

Enjoy breakfast in Hilton Head Island and nearby

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Providing massage services, 255 Captains Quarters offers accommodations in Hilton Head Island. This vacation home provides free private parking, an elevator, and free Wifi.

Featuring massage services, 261 Captains Quarters offers accommodations in Hilton Head Island. This vacation home provides free private parking, an elevator, and free Wifi.

Offering massage services, 251 Captains Quarters features accommodations in Hilton Head Island. This vacation home provides free private parking, an elevator, and free Wifi.

Providing massage services, 232 Captains Quarters features accommodations in Hilton Head Island. This vacation home offers free private parking, an elevator, and free Wifi.

Offering massage services, 241 Captains Quarters features accommodations in Hilton Head Island. This vacation home offers free private parking, an elevator, and free Wifi.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Offering massage services, 234 Captains Quarters provides accommodations in Hilton Head Island. This vacation home features free private parking, an elevator, and free Wifi.

This property offers access to a balcony, free private parking, and free Wifi.

Both free Wifi and parking on-site are accessible at 253 Captains Quarters free of charge. The villa features an outdoor swimming pool and an elevator.

FAQ about cottages in Hilton Head Island

The average price per night for a cottage in Hilton Head Island this weekend is $505 (based on Booking.com prices).
The average price of a cottage in Hilton Head Island this evening is $553 (based on Booking.com prices).
Travelers who stayed in Hilton Head Island near Hilton Head Airport (HHH) had good things to say about Tranquility in paradise- 2 bedroom villa w/parking, Serenity in Paradise, and Seaside Bliss Awaits Your Dream Beach Getaway!.
Seaside 249, Seaside 342, and Hilton Head Resort have received great reviews from guests in Hilton Head Island about the views from these cottages.

Cottages That Guests Love in Hilton Head Island

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Beach + Pool Access: Colorful Hilton Head Condo!

Cottage in Hilton Head Island
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 36 reviews
Location near the little pier on small Fish Haul Beach. Landscaping. Security. Loved the kitchen. Comfortable beds. Quiet, never heard the neighbors, no noise from the parking lot. Not as many tourists as Coligny Beach. Our end unit was the best. The pool and hot tub were sanitary.
Guest review byElizabeth
Group

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