Hilton Head Island Cottage Rentals & Holiday Homes

Find the best cottages in Hilton Head Island - We found 32 exact matches

About Hilton Head Island Cottage Rentals on Madison Vacation Rental

Searching for cottages to rent near Hilton Head Island? Madison Vacation Rental features more than 32 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Hilton Head Island have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Madison Vacation Rental’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Hilton Head Island.

Are you planning to travel to the lakeside, beach, or mountain area? Madison Vacation Rental’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Madison Vacation Rental boasts of 32 holiday cottages and places to stay in Hilton Head Island. The site provides unique Airbnb, VRBO, Madison Vacation Rental-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

Frequently Asked Questions About Hilton Head Island Cottage Rentals

What are the top rated Cottage Rentals in Hilton Head Island?

There are a lot of options in Hilton Head Island. If you plan on staying in the Hilton Head Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Hilton Head Island:

How much does it cost to rent a cottage in Hilton Head Island?

The average cost for a cottage rental in Hilton Head Island is $349 per night. Madisonvacationrental has a wide list of great cottages near Hilton Head Island that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Do you have any rental cottages in Hilton Head Island that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Hilton Head Island to find one that works for you.

Are there quality cottages in Hilton Head Island that have indoor swimming pools?

As of 2026, the data from Madisonvacationrental shows that there are Over 32 private swimming pools or cottages with indoor pools in the Hilton Head Island area along with other great amenities.