Dewees Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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 Inn At Middleton Place

The Inn At Middleton Place

3 out of 5
per person
Sep 24 - Sep 28
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Charleston (CHS)
9/10 Wonderful! (1,001 reviews)
This was a beautiful step back in time. If you are looking for perfection and pristine grounds, this isn’t for you. If you are looking for history, peace, and a quaint place to stay you’ve hit the jackpot.

Reviewed on Jul. 27, 2025

7 Beachwood East by Avantstay Steps to the Beach Ocean Views, Hot Tub, 7bdr

7 Beachwood East by Avantstay Steps to the Beach Ocean Views, Hot Tub, 7bdr

3 out of 5
Beachwood East
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Charleston (CHS)
No reviews
Hotel Richemont

Hotel Richemont

4 out of 5
Charleston Historic District
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Charleston (CHS)
9.2/10 Wonderful! (9 reviews)
The hotel was very nice. We had some problems with the room's patio door would not locking so they moved us to another room witch we didn't like as much (smaller). also, the T.V. didn't have streaming services like Netflix's and such. But other than that, the staff and location was great. Steve

Reviewed on Jul. 27, 2025

Shem Creek Inn

Shem Creek Inn

3 out of 5
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Charleston (CHS)
9/10 Wonderful! (1,002 reviews)
This was a pleasant surprise as we visited charleston and found that mount pleasant was the place to be. This hotel is 10 mins from the beach the pool is top notch and the access to the docks is more than cool. My wife and i enjoyed happy hour during the week at all of the restaraunts and bars along the creek, amazing sunset strolls on the docks and plenty of amazing food options nearby! We enjoyed the stay very much. The hotel is minimal having just what you need but the location and night life is more than worth the stay. Would stay again and would recommend it!

Reviewed on Aug. 5, 2025

Emerson Square

Emerson Square

4 out of 5
Downtown Charleston
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Charleston (CHS)
No reviews

Ready to book your vacation to Dewees Island?

 

Choose your dates

Dewees Island Hotel Deals

Drury Plaza Hotel North Charleston

Drury Plaza Hotel North Charleston

3 out of 5
West Montague Avenue, 2934, North Charleston, SC
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Aug 10 to Aug 11
CA $149
CA $170 total
Aug 10 - Aug 11
includes taxes & fees
9.8/10 Exceptional! (429 reviews)
"Great location! Wonderful showers! Great amenities!"

Reviewed on Aug. 3, 2025

Drury Plaza Hotel North Charleston
The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
387 King St, Charleston, SC
The price is CA $247 per night from Aug 6 to Aug 7
CA $247
CA $281 total
Aug 6 - Aug 7
includes taxes & fees
8.8/10 Excellent! (1,774 reviews)
"Right on the edge of the historic district, perfect for walking. Room had everything we needed & odour free"

Reviewed on Aug. 2, 2025

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 $186 per night from Aug 24 to Aug 25
CA $186
CA $276 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,862 reviews)
Mother Daughter road trip
"I have stayed at this hotel many times and each time I have enjoyed it. The staff is very friendly and the rooms are always on point plus they always have some sort of event happening which is great! I absolutely LOVE their new coffee machine!!! It is awesome! They have a great restaurant if you ..."

Reviewed on Aug. 2, 2025

Harborside at Charleston Harbor Resort and Marina
See all 5,422 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Dewees Island vacation package cost?
You'll find cheap prices from CA $1,419 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.