The Cooper vs. The Dewberry vs. Hotel Bennett: Which Charleston Hotel Should You Actually Book?

Three of Charleston’s most famous and BEST hotels are always competing with each other – but honestly, they’re all right for different people (and they’re all WRONG for different people) so let’s get into the details. 

I live in Charleston and I book all three of these hotels for my luxury travel agency clients constantly. They’re the three names that come up most when people want a walkable downtown stay, with Charleston charm, great service, and a beautiful hotel. Each one gives you a completely different trip. One is on the water with a guests-only rooftop pool. One is the coolest-looking building in the city with no pool at all. One sits up on Marion Square with the prettiest rooms in town.

My verdict: The Cooper wins for most people, especially families, first-timers and anyone coming in summer. Hotel Bennett wins for couples, girls’ trips and anyone whose Charleston is King Street. The Dewberry wins for design lovers on a two-night weekend who care more about a martini on the city’s highest rooftop than a pool.

The Cooper vs. The Dewberry vs. Hotel Bennett at a Glance

	The Cooper	Hotel Bennett	The Dewberry
Neighborhood	Waterfront, French Quarter	Marion Square, Upper King	Marion Square
Opened	2026	2019	2016
Rooms	191	179	153
Entry-level room	About 360 sq ft	About 325 sq ft	About 290 sq ft
Pool	Rooftop infinity pool, hotel guests only	Rooftop pool, heated, hotel guests only	None
Rooftop bar	Bar Marti (guests only)	Fiat Lux	Citrus Club (21+)
Spa	7,000 sq ft, newest in town	Yes	Yes
Best for	Families, first-timers, summer, staycations	Couples, honeymoons, girls’ trips	Design lovers, short couples’ weekends

The Biggest Difference Between Them: Location

All three are walkable, and each puts you closest to a different part of Charleston.

The Cooper sits right on the harbor at 176 Concord Street, at the edge of the French Quarter. You can walk to Waterfront Park in about three minutes and to Rainbow Row in under ten. King Street at Market is about twelve. This is the side of the peninsula most first-timers actually want to see.

Hotel Bennett and The Dewberry are both on Marion Square, about a four-minute walk from each other, at the top of the historic district. That puts you right on Upper King, which is where a lot of the best shopping, restaurants and nightlife live. It also means the walk down to Waterfront Park and Rainbow Row is a real one, about 25 minutes.

Jetset Tip: Decide what your trip is before you pick the hotel. Harbor, history and the pretty postcard streets? The Cooper. Shopping, dinner reservations and bar hopping on Upper King? Bennett or The Dewberry. You can do everything from any of the three, but you’ll do more of the stuff that’s closest.

The Cooper: Best Overall Charleston Hotel

The Cooper is the best hotel in Charleston right now, and I’ll keep saying it.

Charleston is a city built around its harbor, and until The Cooper opened in spring 2026, there wasn’t a single luxury hotel sitting right on the peninsula’s waterfront. Now there is. It looks like it’s been on that block for a hundred years: cream stucco, dark green shutters, deep porches. Inside, Champalimaud Design kept it French Quarter and nautical without tipping into theme park. Tall ceilings, arched windows, seafoam and cream and warm wood.

The Cooper’s rooftop pool is the reason to book

The fourth-floor infinity pool looks straight out over Charleston Harbor, with striped lounges and scalloped umbrellas. It’s open year-round, weather permitting, and it’s strictly for hotel guests. The guests-only part matters more than the view. In a city where rooftops fill up with locals by 11am, The Cooper’s pool stays calm. We always found seats. There’s a shallow entry that works for little ones, and Bar Marti is right there for a Battery Rose Margarita, which is honestly my favorite drink in Charleston right now.

Eating at The Cooper

The Crossing is the signature restaurant, coastal Mediterranean with a Lowcountry twist from Executive Chef Nick Dugan, and dinner there was our best meal of the stay. It’s sleek and chic, a modern vibe. Breakfast on the patio was the sleeper hit. Cooper Coffee & Wine opened this summer (coffee and lunch by day, wine and tapas a few nights a week), and CurrentBurger has a walk-up window on Waterfront Park, which is the easiest lunch you’ll have all trip if you have kids with you. Room service runs 24 hours.

The spa

The Spa at The Cooper is 7,000 square feet with seven treatment rooms (one is a couples room), a Sanarium and a guests-only recovery room with a cryolounger. It’s the newest spa downtown. One thing to know: there are no traditional locker rooms, so plan accordingly.

The honest caveat on The Cooper

The entry-level rooms are the biggest of these three and still tight for a family. We tried a waterfront room without a balcony for the four of us and there wasn’t much floor left once the luggage and stroller came in. For two people, a Waterfront King with Balcony is perfect. For a family of four, the Waterfront Double Queen with Balcony works and the balcony buys you breathing room, but the One Bedroom Suite (a separate living room with a sofa bed) is the real fix. That suite is where The Cooper becomes the best value in Charleston.

Also know there’s a nightly resort experience fee. It covers things you’d likely use anyway (lobby coffee, hosted evening drinks, bikes, the BMW house car around downtown), but factor it in when you compare rates.

Who The Cooper is best for: families who want a real pool, first-time visitors, anyone coming May through September, locals doing a staycation, and couples who want to be on the water and still walk to dinner.

Who should skip it: anyone whose trip is Upper King shopping and bar hopping and who won’t touch the pool. Book Bennett instead.

Want the full deep dive? Read my full Cooper Charleston review, with every room category and my tips for families.

Hotel Bennett: Best Charleston Hotel for Couples and Girls’ Trips

Hotel Bennett is grand and quaint at the same time, which is a very Charleston thing to pull off. It’s a white stone landmark looking down King Street and across Marion Square, built on the site of the old Charleston library, and Condé Nast Traveler readers voted it the number one hotel in Charleston in 2023, 2024 and 2026.

The rooms at Hotel Bennett are the prettiest in Charleston

Freestanding tubs by the windows, soft layered furnishings, and suites with terraces that’ll make you want to cancel your dinner reservation and order in. If you’re celebrating something (a honeymoon, an anniversary, a big birthday), the terrace suites at Bennett are the rooms in town I’d put you in.

The pool and the pink bar

Bennett has a ninth-floor pool, heated year-round and reserved for hotel guests, which means you can actually use it in March. It’s one of the best-run pool decks in town, and you can book a cabana by the half or full day. Fiat Lux, the rooftop bar up there, is open to everyone.

Then there’s Camellias, the pink Champagne bar. Pink marble, mirrors, bubbles, and an afternoon tea Thursday through Sunday that is one of the best ways in Charleston to spend two hours with your mom or your four best girlfriends. Gabrielle is the signature restaurant over Marion Square, and La Pâtisserie, run by pastry chef Rémy Fünfrock, is my favorite coffee-and-a-croissant stop on Upper King whether you’re staying there or not.

The honest caveat on Hotel Bennett

The entry-level rooms are on the smaller side, about 325 square feet, so book up a category if you can. And remember the location. Bennett is perfect for Upper King and about a 25-minute walk to the waterfront. It also leans adult. Families are welcome and kids can eat at every outlet, but there’s no kids’ program, and this is a couples and girls’ trip hotel first.

Jetset Tip: If you’re bringing kids to Bennett anyway, look at the King’s Club, the club level. Children 12 and under are complimentary on it, and there’s food out from 7am to 9pm, which almost nobody knows.

Who Hotel Bennett is best for: couples, honeymooners, anniversaries, girls’ trips and anyone building their weekend around King Street. Planning a Charleston girls’ weekend or a Charleston bachelorette? Bennett puts you on King Street with Camellias downstairs.

Who should skip it: families with little kids who want to spend afternoons by the water, and anyone whose dream Charleston is Rainbow Row and the harbor.

The Dewberry: Best Charleston Hotel for Design Lovers

The Dewberry is my third pick of these three, even though I’ve recommended it for years. Here’s why.

The Dewberry is the coolest-looking hotel in Charleston

It lives inside the former L. Mendel Rivers Federal Building from the 1960s, which John Dewberry bought in 2008 and opened as a hotel in 2016, and the result is Charleston’s best midcentury modern moment. Brass, walnut, marble, custom millwork, gorgeous light. Nothing else in the city looks like it. The Living Room downstairs is the best hotel bar in Charleston for a quiet drink, and the spa (Natura Bissé products, a treatment menu by Lydia Mondavi) has been one of my favorites in town for years. It also holds a Michelin Key, and was named Best Independent Hotel in the World by Virtuoso in 2025.

The Citrus Club rooftop

The Citrus Club, up on the eighth floor, is the highest rooftop bar in Charleston, with steeples and skyline and harbor all laid out in front of you. It’s an amazing sunset drink. It’s 21 and over, there’s a dress code (no swimwear or athletic wear), and seating is first come, first served, so on a busy evening you may wait for a table on your own hotel’s rooftop.

The honest caveat on The Dewberry

The rooms are small. The entry-level rooms start around 290 square feet, and unlike The Cooper and Bennett, there’s no pool downstairs to make up for it. In July and August in Charleston, that’s a real cost. Food is also limited to The Living Room, the Citrus Club and in-room dining, since the hotel’s old restaurant, Henrietta’s, closed in 2020 and hasn’t been replaced. And there are no rollaway beds, so families need a two-queen room or a suite.

None of this matters on a two-night couples’ weekend in October. On a five-night summer trip with kids, it adds up fast.

Who The Dewberry is best for: design lovers, couples on a short weekend, and anyone who’d rather have a great bar and the best rooftop view in the city than a pool.

Who should skip it: families, summer trips, and anyone who wants pool afternoons.

Jetset Tip: If you book The Dewberry, book bigger. The Charleston Flats are around 511 square feet with a freestanding tub and the size issue disappears completely.

Head to Head: Which One Wins for Your Trip?

Best for families: The Cooper. The pool, the one-bedroom suites and the walk-up burger window settle it.

Best for a honeymoon or anniversary: Hotel Bennett, in a terrace suite.

Best for a girls’ trip: Hotel Bennett, for the pool and Camellias.

Best for first-time visitors: The Cooper. You’re on the water and the postcard part of Charleston is right outside.

Best for summer: The Cooper. Bennett’s heated pool is the runner-up, and The Dewberry has none.

Best for design: The Dewberry, and nothing else is close.

Best pool: The Cooper’s harbor view, guests only.

Best rooftop bar: The Dewberry’s Citrus Club for the view, as long as you get there early.

Best spa: The Spa at The Cooper, the newest in town. The Dewberry’s spa is the runner-up and a longtime favorite of mine.

FAQ: The Cooper vs. The Dewberry vs. Hotel Bennett

Which is better, The Cooper or Hotel Bennett?

For most people, The Cooper. It’s on the waterfront, it has a guests-only infinity pool over the harbor, and its family rooms are the most useful downtown. Hotel Bennett is the better pick for couples and girls’ trips centered on King Street, and its terrace suites are the prettiest rooms in Charleston.

Does The Dewberry Charleston have a pool?

No. The Dewberry has no pool. Its rooftop is the Citrus Club bar on the eighth floor, which is 21 and over with first-come seating. If a pool matters to you, book The Cooper or Hotel Bennett.

Does Hotel Bennett have a rooftop pool?

Yes. Hotel Bennett has a ninth-floor pool, heated year-round and reserved for overnight guests, with bookable cabanas. Fiat Lux, the rooftop bar on the same floor, is open to everyone.

Is The Cooper Charleston on the water?

Yes. The Cooper is directly on Charleston Harbor at 176 Concord Street, and it’s the only luxury hotel right on the peninsula’s waterfront. Waterfront Park is about a three-minute walk.

Are The Dewberry and Hotel Bennett close to each other?

Yes. They’re about a four-minute walk apart on Marion Square, at the top of the historic district, so they share the same easy access to Upper King Street.

Which Charleston hotel is best for kids?

The Cooper. There’s no kids’ club at any of these three, but The Cooper has a shallow-entry pool, one-bedroom suites with sofa beds and easy casual food like CurrentBurger. Bennett welcomes kids but skews adult, and The Dewberry has no pool and no rollaway beds.

Which has the best rooftop in Charleston?

For views, The Dewberry’s Citrus Club, which is the highest rooftop bar in the city. For a rooftop you can actually swim and lounge on, The Cooper.

How do I get free breakfast at The Cooper, The Dewberry or Hotel Bennett?

Book through a luxury travel advisor with preferred partner status at the hotel. When you book any of these three with me, you pay the same rate as booking direct and get a daily breakfast credit for two, a $100 credit, an upgrade on arrival when available, early check-in and late check-out when available, and VIP recognition on property. Here’s how using a luxury travel advisor works.

So Which Should You Book?

If you want me to choose for you, it’s The Cooper. It’s what I’d book for my own family and what I recommend to every first-timer, and it makes a Charleston summer trip easy.

Book Hotel Bennett if your trip is romance, celebrations or a girls’ weekend on King Street. Book The Dewberry if you’re coming for two nights, you love design, and your perfect evening ends with a drink on the city’s best rooftop.

Whichever one you pick, book it through me. You pay the exact same rate you’d pay booking direct, and I layer on daily breakfast, a $100 credit, an upgrade when one’s available, early check-in and late check-out when possible, and VIP recognition on property. I’ll also send you my list of the Charleston restaurants locals actually fight for, plus my tips on how to get a table at Chubby Fish.

Fill out this inquiry form here and I’ll help you plan your trip, or you can go directly to my travel portal and see my exclusive travel advisor rates and book yourself with all of my perks included! The password is always JETSETTERS (save this page to your bookmarks for future trips!)

For everything else, start with my Ultimate Charleston Travel Guide.