Family Fun, Even for the Dog: A Review of the Hyatt Regency Chesapeake Bay Resort

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The resort experience is what many people in the Northeast look for in a vacation. Fly someplace warm like Florida or the Caribbean, stay in a nice hotel with a beautiful view, and have lots of stuff to do in addition to lounging by a blue-water pool and consuming boozy drinks with little umbrellas in them. The challenge for many people for vacations like this are primarily the time and the flight cost to get there, especially if you're traveling with kids. It's difficult to justify the expense of going for just a few days. But what if you could have that resort experience where the door-to-door travel time is only three to four hours each way for the cost of a tank of gas? And even better, what if you could do it mostly for free on points?

The Hyatt Chesapeake Bay Golf Resort, Spa and Marina makes the perfect family getaway without having to blow too many vacation days -- or Hyatt points. You can even bring the family dog. We did, and my family enjoyed it.

Booking

Recently reduced from a Category 5 to a Category 4 hotel in the World of Hyatt program, the resort costs 15,000 points per night. Cash rates run between $160 and $289 per night, depending on when and how far out you book, or about what you'd pay for most similar resorts elsewhere. TPG values Hyatt points at 1.7 cents each, making this a solid redemption, especially during the high season. They also charge a not-so-terrible daily resort fee of $25 to $32, depending on the time of year. All tiers of World of Hyatt members waive resort fees on award stays.

Speaking of award stays, since Chase Ultimate Rewards points transfer to World of Hyatt at a 1:1 ratio, earning points for Hyatt stays is incredibly easy. For example, if you signed up for the Chase Sapphire Preferred Card and then earned the 60,000-point sign-up bonus (after you spend $4,000 in the first three months from account opening), you'd already have enough points to book a four-night stay at this property -- perfect for a midsummer family trip.

I booked a king room and used a Globalist suite upgrade to get a premium suite with a water view. I also booked a connecting double room for friends who we invited along to join us.

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Location

The Hyatt Regency Chesapeake Bay is in Cambridge, Maryland, about a four-hour drive from New York City, three hours from Philadelphia and two hours from Baltimore. Built in 2002 and recently renovated, the 400-room resort sits on 342 acres just off the Chesapeake Bay on a tributary called the Choptank River.

We drove down from New York City in a little over four hours with a pit stop.

Check-in

We arrived just after lunch, and a bellman collected the luggage from our car. We were offered a choice of $21-a-day valet or free self-parking. Valet parking was free on award stays for Globalists, but we chose to self-park anyway, as it was really close.

The lobby was open and inviting, with high, vaulted ceilings and a view across the water. The reception counter was well-staffed, and we were delighted to learn the rooms were ready early, even though check-in is usually 4pm. Refreshing cucumber water was available in the lobby overlooking the bar called Michener's Library, which was down one level.

The bellman then escorted us to our room.

Room

There were a bunch of different-sized rooms, suites, petite suites to suit any group. Some even had bunk beds. The room we received (thanks to being a lifetime Globalist) was the Admiral Suite, a 1,200-square-foot, gorgeous residence on the top floor.

The foyer of the suite was grand, marbled and flowed with the nautical theme of the hotel. It also had a half bath to the side.

The living room featured a sitting area with a sofa, comfy chairs, a large TV and a gas fireplace. There was also a desk, credenza and a dining area with a huge circular table, which we used later in the evening for board games. A wet bar was stocked with bottled water in a refrigerator, and there were a bunch of plates and glassware. There was also a separate wine fridge, but I couldn't ever bring enough wine to fill it. A wraparound balcony offered fabulous views of the river, the marina and the pool.

The spacious bedroom had its own wraparound balcony, a comfortable king bed, another gas fireplace and a walk-in closet.

The focal point of the marble bathroom was a large Jacuzzi. Dual vanities, a rainfall shower and a separate toilet rounded out the bathroom. I found it to be warm and inviting, if not a bit dated. Designer toiletries and fluffy, white towels were in abundance.

The suite was every bit as nice as any suite I've ever been fortunate enough to stay in at any other Hyatt resort in the world. Some of the furnishings were a bit dated, but all were in good condition. There was plenty of room to spread out, and it was big enough to fit a rollaway for our daughter.

The hotel provided a dog bed, bowls and treats for the extended family. Most of the time, the hotel puts dog owners in a first-floor room or suite so you have easy access to a patio and the grass beyond. They also charged a nominal pet fee that pays for deep cleaning the room afterward. It's still cheaper than paying someone to care for Fido back home.

Regular deluxe rooms were pretty spacious, and most had a balcony or a patio.

Food and Beverage

Water's Edge is the hotel's main restaurant. It's located on the first floor and features towering ceilings and an open kitchen. The breakfast buffet was pretty standard and a good value, and there were also a la carte options. They did away with the Regency Club a couple of years ago, turning it into a wedding space, so complimentary breakfast was provided for Globalists in this restaurant.

For dinner, the menu was classic American grill, featuring steaks, fish and the most ridiculously amazing grilled pork chop I've ever had. The crab soup was also excellent, as were the crabcakes. This was Maryland, after all, and you shouldn't leave without having crab in some form.

The kitchen was sensitive to allergies, which was good because my daughter, like many people, has a shellfish allergy. The cost was the same or perhaps a bit less than you'd expect at any other resort. We've all most certainly paid more for resort food that wasn't very good. The food here was worth it.

There was also a separate seafood restaurant called Blue Point Provisions, a short walk down a crushed-oyster-shell path toward the marina and with a lovely view of the water. Offering both indoor and outdoor seating, the food there was also quite excellent, with a great cocktail menu and an extensive selection of fresh oysters.

For a more casual dining experience, Michener's Library was a bar and served mostly bar food. There were also a couple of pool tables on the far side.

Amenities

Three substantially large pools surrounded by small palm trees provided multiple opportunities for both action and quiet. There was a freeform family pool complete with a cool waterslide, a quieter, mostly adults-only pool with ample chaise lounges and a huge indoor pool with side doors that gave it an airy, indoor/outdoor feeling. At night they showed children's movies in the indoor pool for "dive-in movies" complete with popcorn. There was also an indoor/outdoor hot tub.

Family pool.

Tropical drinks and light lunches were served poolside, and a steel-drum band provided entertainment the weekend we were there. You didn't need to drink that much to think you were in the Caribbean. They also had a daily kids activity schedule.

Water activities included Jet Skis, paddleboards canoes all at rates the same or less than you'd pay down in the islands. There was also a small, sand beach leading to calm water.

Other activities included tennis, beach volleyball, miniature golf and a scenic, championship 18-hole golf course and driving range.

I bought some cheap fishing gear at the Walmart across the road, got worms from the marina shop and took my daughter fishing off the dock. That's something a city kid doesn't get to experience too often.

The hotel also had a cool game room with free table tennis, foosball and air hockey, as well as a few coin-op games. A little store nearby sold snacks, ice cream and s'mores kits. While I'm not a big s'mores fan, it's a fun rite of passage to make them with your kid, and they had a huge outdoor fireplace just for that purpose.

A well-equipped fitness center, a full-service spa and a Camp Hyatt rounded out the other resort amenities.

There was also no shortage of quiet trails and spots under a shady tree, on the water or elsewhere on the scenic property to do absolutely nothing, read or just reflect.

Overall Impression

I've stayed at this property a few times over the years, but bringing the family dog on vacation with us was really unique and added a wonderful dimension to the long weekend we were there. He had so much fun. Service was generally good, but like most resorts, sometimes they get overwhelmed and it slows down a bit.

All photos by the author.

A previous version of this story stated that this property was a Category 3 World of Hyatt hotel, but it is fact a Category 4. The story has been updated to reflect this.