Dewees Island Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Dewees Island Vacation

Let our vacation packages to Dewees Island inspire your next getaway. You'll find loads to love about this vibrant city, starting with the neighborhood of Daniel Island, which is good for nature and golfing. Any trip to Dewees Island needs a well-designed itinerary. Fill yours with major attractions such as Wild Dunes Resort Golf Course, Front Beach and Isle of Palms Beach. Check out Expedia's extensive range of travel options and book your ultimate vacation to Dewees Island today.

Top Dewees Island Vacation Deals

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

The Ryder Hotel

3.5 out of 5
Charleston Historic District
Price was CA $2,571, price is now CA $1,915 per person
CA $1,915
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charleston (CHS)
8.8/10 Excellent! (1,241 reviews)
Great location to everything - cute little hotel

Reviewed on Nov 9, 2026

The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
Charleston Historic District
Price was CA $2,938, price is now CA $2,211 per person
CA $2,211
per person
Dec 23 - Dec 30
found 1 hour ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Charleston (CHS)
9/10 Wonderful! (2,610 reviews)

Emeline

Emeline

4 out of 5
Charleston Historic District
Price was CA $3,035, price is now CA $2,361 per person
CA $2,361
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charleston (CHS)
9.4/10 Exceptional! (1,779 reviews)

Planters Inn

Planters Inn

4.5 out of 5
Charleston Historic District
Price was CA $2,416, price is now CA $1,956 per person
CA $1,956
per person
Jan 28 - Jan 31
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Charleston (CHS)
9.6/10 Exceptional! (1,001 reviews)

The Ansonborough

The Ansonborough

4 out of 5
Charleston Historic District
Price was CA $3,551, price is now CA $2,885 per person
CA $2,885
per person
Dec 23 - Dec 30
found 1 hour ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Charleston (CHS)
9.4/10 Exceptional! (1,187 reviews)
Everyone was super nice and helpful. Grabbed a drink at the bar the first night and enjoyed the sunset on the rooftop. Comfy bed and pillows. Great water pressure in the shower. Somehow ended up with an extra king bed in a second lofted bedroom - room 336. Would 100% visit again! Parking close and easy. Breakfast was average but welcome as it was included.

Reviewed on Nov 9, 2026

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Dewees Island Hotel Deals

The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
387 King St Charleston SC
The price is CA $291 per night from Nov 29 to Nov 30
CA $291
CA $332 total
Nov 29 - Nov 30
includes taxes & fees
The Francis Marion Hotel
Harborside at Charleston Harbor Resort and Marina

Harborside at Charleston Harbor Resort and Marina

4 out of 5
20 Patriots Point Rd Mount Pleasant SC
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Nov 18 to Nov 19
CA $113
CA $195 total
Nov 18 - Nov 19
includes taxes & fees
8.6/10 Excellent! (2,296 reviews)
"Great room had a view of the water. Great staff."

Reviewed on Nov 9, 2026

Harborside at Charleston Harbor Resort and Marina
Emeline

Emeline

4 out of 5
181 Church St Charleston SC
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Nov 29 to Nov 30
CA $246
CA $352 total
Nov 29 - Nov 30
includes taxes & fees
Emeline
See all 5,316 properties in Dewees 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.
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Frequently asked questions

How much does a Dewees Island vacation package cost?
You'll find cheap prices from CA $1,915 on Expedia for your Dewees Island escape. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Dewees Island costs.
What are the cheapest months to go to Dewees Island?
If you're looking to score a cheap Dewees Island vacation package, consider visiting in January, February and November. You're likely to find better prices on hotels and airfares during these months — perfect for budget-conscious travellers.
How many days is enough for Dewees Island?
We suggest planning a Dewees Island vacation for a minimum of 2 days. This gives you enough time to visit key attractions such as Isle of Palms Marina and Isle of Palms County Park, and explore neighbourhoods like Pelican Bay and Twin Oaks. You could even make time for a day trip outside of Dewees Island.
How to find the best Dewees Island package deals?
Bagging a cheap Dewees Island package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Dewees Island package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Dewees Island vacation as a package?
You can enjoy significant savings on your next Dewees Island getaway by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Dewees Island?
Score fantastic discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Dewees Island adventure.
How to plan a trip to Dewees Island?

  1. Choose when to get away: Check your calendar and pack your bags. Your favourite season and the activities on offer will also help you decide when to escape to Dewees Island.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will probably be the biggest expense during your trip to Dewees Island.
  3. Work out your trip length: Consider how much time you want to spend exploring Dewees Island. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Dewees Island vacation package that brings all your bookings together.

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