happyly approved

Inn at Perry Cabin

308 Watkins Ln, St Michaels, MD 21663

Year round

$$$$

restaurants, road-trips

For true relaxation, kick back at the beautiful Inn at Perry Cabin.

If a luxury getaway is your preference, the five-star Inn at Perry Cabin is just past the village of St. Michaels. From a beautiful pool to dock access with boats available and daily sailing lessons for the whole family, a spa, golf course, and many varieties of rooms and suites, this hotel certainly feels like paradise.

The concierge services and varied amenities are top-notch, and while it can get quite pricy, you won’t regret it if your intention is to be pampered. It is located on the way toward Tilghman Island, and it’s nestled far from the road adding to the feeling of isolation and quiet.

It is a wonderful place to escape any feeling of the hustle and bustle of daily life, with plenty of opportunities for activity, with bikes, boats, and activities of all kinds for adults and children (they even have green clay tennis courts!), but is is also serene and romantic, so there is something for every vacation style preference. Kid's are certainly welcome, and the feeling of serenity on this special property seems to be contagious, even to active little ones. 

You can easily ride bikes to the shops and restaurants in town, and we recommend getting a crab fix at The Crab Claw, dine at Awful Arthurs or grab coffee and picnic supplies at Eat Sprout Cafe. Cupcakes are popular at Jojo's and shakes at Justine's - you can get ice cream at both!!

For some playtime, Perry Cabin Park is very close, or take a drive out to the secret beach in Claiborne to splash around.

Features

Good for All Ages Boating Swimming
Thoughtfully captured by:
Caitlin Iseler
Caitlin Iseler, happyly founder and CEO, was born in New York and is one of eight children. Her favorite holiday is Thanksgiving and the chance to sit at one table with her favorite 40 people. Caitlin, her outdoor loving husband, Thomas, and daughter, Hanah, live in Virginia Beach. She is also blessed to be a bonus mom to 2 incredible humans, Max & Elizabeth. Being a mom has always been something she dreamt of and it brings her joy beyond measure. Before starting happyly, Caitlin spent 15 years working in executive search with technology companies, most recently with Korn Ferry. In what seems like a lifetime ago, she attended the University of Virginia and was a member of the National & ACC Championship Teams, a gift that keeps giving.
More activities by Caitlin
3-mile out and back run or walk in the heart of DC.
Great public pool in the West End neighborhood.
An older playground with views that never get old, and running routes too!

Recommended Gear