We just got back from a long weekend at The Inn at Perry Cabin, and I had to hop on here and share everything about it before I forget the little details. I know Maryland seems far, but actually, it’s about 4.5 hours from Connecticut, which is similar to driving to Maine or Vermont, and it proved worth the drive! We have friends in DC so it was a great meeting spot, and they have a Pete Dye golf course Andrew was interested in playing and I have always wanted to check out the Inn at Perry Cabin, so we decided to make a weekend of it. We’d been wanting a low-key but still luxe-feeling family getaway—something that would feel like an escape but not a production. This charming waterfront resort in St. Michaels, Maryland — which you may recognize from Wedding Crashers — is exactly what we wanted for a weekend getaway with the kids. Honestly, had I known we’d love it this much, I would have stayed longer.
I was a little worried about bringing the kids to this luxury resort, which hosts weddings and honeymoons and babymoons, but it truly was so family-friendly and a huge part of that was how accommodating the staff was, how easy they make everything, and all the things right on-site to do.
I got so many questions about our trip so I thought I’d compile a full recap of our family getaway to the Inn at Perry Cabin.
What Kind of Accommodations for Families Do They Have?
We booked one of the larger suites and it was perfect for our circus of six. The layout gave us actual breathing room. There was a living room/dining room area with its own powder room and then a large main bedroom with a huge en suite bathroom. The hotel set up two cots in the main room, which also has a pullout sofa and they provided a crib for us for Grace (complete with baby products for us to use). We ended up setting up our travel crib (that we had brought just in case) in the bathroom since it was so large with the Slumber Pod for Brooks and having the two bigs sleep in the main room and Grace in the crib in our room (she sleeps in our room at home still as well), and it worked out great. If Brooks was better at staying in bed, we could have put him on the pullout, but having him in a separate room worked out better. There was so much space, we could have put Grace in the main room or the hallway by the powder room too.
One of the best parts about the hotel is how accommodating and responsive their concierge is. They text you before you arrive and you can just respond with any requests, so I asked for a crib and made golf and spa and restaurant reservations that way while I was running the kids around. And then anything I needed while there, I could just text.
The design of the hotel is so charming. I kept taking pictures as inspiration for our home (or future beach home). It has New England-meets-coastal vibes with white shiplap, plush bedding, and a fireplace that made evenings feel like a Nancy Meyers movie. And bless the blackout curtains. I actually got the kids to sleep past 6am one morning. There are so many charming details throughout the hotel and lots of antiques and artwork I wanted to steal. Seriously, my camera roll is half our family photos and half design inspo.
How is The Inn at Perry Cabin’s Location?
The Inn is located right on the Miles River in historic St. Michaels, and it honestly feels like something out of a postcard. It’s about a 2-hour drive from D.C. and a little over 3 from NYC and a bit over 4.5 hours from where we live in Connecticut. So it’s close enough for a long weekend, but far enough to feel like you’ve escaped.
The town of St. Michaels is super walkable, filled with boutiques, ice cream shops, home stores I could have spent hours in, and the cutest toy store my kids begged to go back to. There are lots of charming restaurants and ice cream spots and coffee shops, but it’s small and walkable and just so so charming (have I said that enough?).
What On-Site Activities & Amenities are There for Families at The Inn at Perry Cabin?
I was so impressed with how family-friendly everything felt without losing that calm, luxurious vibe. We spent the majority of our time just enjoying the property during our family getaway to the Inn at Perry Cabin. The property features huge, sprawling, and made for kids who need to run after being in the car too long. They had croquet and lawn games already set up, and there’s also Bocce and corn hole and lots of other fun ways the kids can burn energy.
There are bikes on property (including some kids bikes and a tandem bike) that you can just take — you don’t have to check out. So it’s just so easy to grab a bike and go for a ride around the property or even into town. They have helmets too! They also have baby joggers if you need! They also have kayaks and paddle boards you can take out. I loved how you can use so many of the things the resort provides without checking everything out or reserving in advanced, which is nice when you have young kids and don’t want to have to be on a schedule and stress about getting to a reservation on time.
The heated pool was definitely where we spent a lot of time. It’s big enough for the kids to splash without bothering anyone and I appreciated the temperature (I hate pools because they’re usually so cold and this one was the perfect temp). The poolside service made it so easy. We ate lunch there one day and got snacks there another. They even brought out little popsicles for the kids one afternoon.
They have a fleet of gorgeous boats, from sailboats to yachts that you can book for all different types of trips. We took the resort’s private sailboat out for a quick cruise, which was magical. Grace fell asleep on my chest as we glided along the river, and the kids still haven’t stopped talking about it. It was like something out of a movie and the staff was so amazing with them.
They also have a Pete Dye golf course (which Andrew played a loved!) and a full spa (I got the best massage) as well as a fitness center that I peeked in and looked amazing but never made it to. They have tennis courts and offer cardio tennis and clinics for kids too, as well as garden tours (the gardens on property are insanely beautiful) as well as other activities like Rum tasing and sip and paint. They also do a 5pm toast by the waterfront and it was such a special experience. They even provided alcohol-free bubbly for my kiddos and they sat and listened to the history of the property and then told us all about it at dinner (we were too busy chasing Brooks to listen to it).
The Food
Okay, the food. I was genuinely blown away at how good the food was — in fact, it was a highlight of the tirp.
- Stars Restaurant – The main dining room is super nice and offers a tasting menu for dinner, but kids are welcome and you don’t feel at all weird bringing yours. They brought crayons and a coloring menu without me even asking and had a full kids menu. We were able to enjoy the tasting menu while the kids ate their pasta and it was perfect. It was such a good meal. 10/10 recommend.
- High Tide Bar – Perfect for casual lunches. Andrew said the lobster roll was the best he’s had outside of Maine. It’s a great spot to eat while the kids play corn hole nearby
- Room Service – Breakfast in bed is my favorite on vacation and my kids love it so we did that one morning.
Okay, I think that sums up everything from our family getaway at the Inn at Perry Cabin. The Inn at Perry Cabin is elegant but relaxed, refined yet kid-friendly, luxurious but full of heart. As a mom of four spirited kiddos, I’m always nervous about whether a place is really ready for young families — but this one nailed it. It’s hard to find resorts that we really enjoy and feels like a special treat for us but is also kid-friendly enough and the Inn at Perry is that. But I’d also love coming here for a couple’s getaway or with my girlfriends.
Let me know if you have any questions or want more info — I saved a highlight reel on my Instagram as well.
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