Perfect for a Family Weekend Getaway: A Review of the Hyatt Regency Chesapeake Bay

Executive Summary

The Hyatt Regency Chesapeake Bay resort in Cambridge, MD is the perfect place for a family weekend getaway. Its a 1.5-2hr drive from a lot of places in the Washington DC, Maryland and Virginia (DMV) area, including major airports (BWI, and DCA for example). Although the cash rates can get pricey depending on the season, you can easily get at least one free night per year by signing up for a World of Hyatt Credit Card. There are plenty of activities to keep you busy at the resort (pools, golfing, bars, restaurants, the occasional live entertainment) and prices appeared to be more reasonable than at the typical resort with a captive audience. If you need to get away for a bit, you can drive into town in 10 minutes where you’ll have a good mix of restaurants, breweries, and other activities. Please check out our Instagram (@moononfi) for more pictures.


I think we found a new spot for a yearly family vacation. And by “new” I mean first. You see, we’re still a relatively new family and we’ve been busy making babies, paying down debt, working and making money, etc., and we haven’t had time to settle into a routine, like the typical American family that visits the same location, stays in the same house, on the same date, year after year. And actually, the thought of that sickens me a little bit. But I can also see it has it benefits. After visiting the Hyatt Regency Chesapeake Bay in Cambridge, MD, things may be about to change.

Location and Commute

It took us ~2hrs to drive to the resort. Just long enough before our kid starts asking if we were there yet. We took a half day of vacation on a Friday, with the intention of getting there right at check in time. Unfortunately, it took a little longer than expected to hit the road, which also meant we ran into a little bit of work traffic.

Our Itinerary and Recommendations

We touched down on a mid Friday afternoon. I checked in online so I knew our room was already ready. We grabbed our keys and immediately went to change into our bathing suits. There are a total of 3 pools on the property. The main pool, the infinity pool that oversees the bay, was partly reserved for adults only during our stay. We used the other half of this pool along with other families because this pool had an awesome view and there were no cannons spitting out water or balls flying in the air.

Infinity pool overlooking the Chesapeake Bay
Infinity pool overlooking the Chesapeake Bay

The outdoor family pool that is off to the side is more ideal for families with active kids that are a little older. There was a mild slide for the smaller kids, basketball courts, volley ball nets, etc.

Family pool at the Hyatt Chesapeake
Family Pool

Lastly, there is an inside pool that is also very rambunctious. This is where the daily poolside movie night is hosted. This is also where you will find the indoor/outdoor hot tub / jacuzzi.

Indoor pool and hot tub showing movie projector
Indoor pool and hot tub

After pool time we went back to the room and changed so we can get some food. It was recommended that we check out Blue Point restaurant, which was located on the resort. However, we discovered that it was not within walking distance. So we stayed right where we were and had dinner at Michener’s Library. The service was a little slow, but the prices were reasonable given the circumstances, and we got some live music with our dinner.

Day 2 started off with breakfast at the resort’s Water’s Edge buffet. On the surface, the prices were reasonable. But, Im not big on paying for regular food that I can make at home. I.e. eggs, oatmeal, toast, pancakes, etc. Next time I’ll vote to skip the buffet and grab something outside of the property. After some more pool time, we decided to drive off property for lunch. The downtown area is a short 10-15 minute drive. We ate lunch at Jimmie & Sooks. I tried the crab sandwich which I inhaled it in 2-3 bites. It was that good! My wife had some sort of BBQ combo which was a pretty decent size portion. This is the type of meal my wife would normally not finish, unless she’s pregnant. After lunch we walked around the area and found the Harriet Tubman Museum & Educational Center. There was a gorgeous mural painted there recently that I had to see in person. We headed back to our rooms where nap time turned into sleep time. I went off property again for Chinese food. We ate, chatted and eventually went back to sleep.

On our last day, we got up and went into town again for breakfast. Much wiser choice. When we got to the hotel, I called to see about late checkout, but the hotel was not able to grant it. So we packed up our stuff, but changed into our bathing suits and took a change of clothes so we could head out after we ere done. This worked out perfectly.


We spent a total of $221 during our 2-night stay stay. The majority of this ($211 to be exact) were food related.


We ate the resort twice and spent $103. Our first night we had dinner at Michener’s Library where I was pleasantly surprised to find a Beyond Meat burger on the menu. The following morning we indulged in the buffet option at the Water’s Edge Grill Restaurant. Kids under 5 years old are free at the buffet which is great for a big family. Otherwise, I recommend skipping this breakfast option and going into town.

Outside of the resort we spent $108 on food. We went to Jimmie & Sooks for lunch (10 minute drive) and had some bomb meals. We also found a Chinese restaurant right outside of the resort where we had takeout dinner. My wife is really particular about (American) Chinese food and was not a huge fan. On our last day we drove into town again for breakfast at Black Water Bakery where I stamped my millennial passport by ordering the avocado toast.


You’ll notice that the cost for the stay is not included in these figures. Thats because we are holders of the World of Hyatt Credit Card and were able to use our yearly free night certificate plus 15k points for this stay. This card comes with a $75 yearly fee which would probably be prudent to tack on to the cost of this trip. With that being said, cash rates were $350/night at the time that we were making our reservations and climbed to $600+ (based on conversations we had with other guests) during our stay.

Bottom Line

Immediately upon returning from the trip, I sent some of our close friends links to sign up for the World of Hyatt credit card. I can’t say I’d be comfortable spending $1,000+ to stay here, but the place is relaxing and I think there is something to do here for everyone. The main appeal for us was the short(ish) drive, but also that we get to redeem our free night certificate. So if you’re looking for a Hyatt property where you will get a good bang for your points for you and your family, give the Hyatt Regency Chesapeake Bay a look!

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