Fabulous Fall

St. Michaels is fabulous in the Fall.  And, Five Gables Inn & Spa is making Fall even more fabulous. Stay one night midweek and receive the 2nd night ½ off! This special is available Sunday thru Thursday excluding holidays and cannot be combined with any other discounts or packages. Don’t miss out on this very special offer!


Did you know we are dog friendly at Five Gables Inn & Spa. We have 4 rooms and a suite that are dedicated to our guests who love to travel with their four legged friends. We have beds and dog bowls that we lend our furry guests. And, we give each and every one of our four legged guests a treat and a toy from Flying Freds. We really love to pamper all of our guests here! And of course, we suggest a visit to Flying Freds – our upscale pet boutique – even if you don’t bring a furry friend with you.

Spectacular Fireworks

Fireworks were spectacular this year. They lit up the sky over St. Michaels with brilliant colors and loud explosions. Guests at Five Gables enjoyed the festivities on the lawn at the Chesapeake Bay Maritime Museum. This is always a prime spot on the Miles River for viewing fireworks. And, this year, our guests also enjoyed the big band sounds of the Rhythm Doctors, a favorite group at the CBMM. Put this event on your calendar for next year – fabulous fireworks, great music and a relaxing stay at Five Gables Inn & Spa – it couldn’t be any better!


Come join us for Fireworks In St. Michaels! The show will be bigger and better than ever! Stay with us at Five Gables and receive tickets to the Chesapeake Bay Maritime Museum for a night of great music, dancing and the best fireworks display on the Chesapeake!

Summer in St. Michaels………

Summer in St. Michaels – steamed crabs, sailboat races on the Miles River, the Farmers Market, lazy walks around town, festivals at the Chesapeake Maritime Museum, dinners at fabulous restaurants, shopping in unique boutiques, relaxing afternoons around our indoor pool, a massage or a soak in your own Jacuzzi tub…it doesn’t get any better than spending time at Five Gables Inn & Spa.

Retire to St. Michaels………

Come and stay at Five Gables Inn & Spa to find out why Money Magazine name St. Michaels one of the top 3 cities to retire to.

Experience the laid back charm, historic houses and delicious restaurants first hand.  Tour the Maritime Museum and learn about the Chesapeake Bay.  Take a boat ride on the Miles River or just enjoy a massage, the sauna, steam room and indoor pool during your stay at Five Gables.

It’s Back!!!!!

Five Gables’ most popular package – the one and only Spa and Sail Package begins on May 1st.

Sail on one of the oldest skipjacks on the Chesapeake, the Rebeca T. Ruark. This boat is listed on the National Historic Register and opened Good Morning America several years ago. She is owned and sailed by Captain Wade Murphy . Captain Wade is a third generation waterman and shares all his great stories with his “crew”.

After the sail, come back into St. Michaels and enjoy a dozen crabs and a pitcher of beer at the iconic Crab Claw – the original crab house in St. Michaels.

This package also includes accommodations for two people for two nights and two 1-hour massages. It starts at $600.00 for a midweek stay.

Spring into Five Gables Inn & Spa

Spring is a great time to visit St. Michaels!  Daffodils are blooming, window boxes are full of pansies, shops are open and new merchandise is arriving daily, restaurants are offering new menus and new specials.  Everything looks crisp and new.

Five Gables is offering our Spring Package during April.  This package includes two nights for two people, a 1 hour massage each, a spring daffodil basket and chocolates.

This package starts at $440.00 for two nights midweek.

Local Wine & Beer Tastings

Tasting Room-- St. Michaels Winery
Tasting Room– St. Michaels Winery

St. Michaels has long been known for fine dining, with a variety of top notch restaurants featuring regional cuisine. In recent years, we’ve also gained recognition for the wonderful local wine and beer from St. Michaels Winery and the Eastern Shore Brewing Company, both of which have tasting rooms located in downtown St. Michaels, a short walk up Talbot Street from Five Gables.

St. Michaels Winery was founded in 2005 and offers an array of fine wines made from grapes grown in their Henderson and Wye Mills vineyards. Their wines have won a number of awards, including the Maryland Governor’s Cup “Best in Class” and the Maryland Winemasters Choice Gold Medal. The tasting room is open daily without appointment. You can also contact the Winery ahead of time to schedule a private tasting for a group of 10 or more. Each tasting is conducted by a trained member of the St. Michaels Winery staff and includes wine, a souvenir wine glass, and sample cheeses from Chapel’s Country Creamery.

The Eastern Shore Brewing Company opened in 2008 and has a tasting room located right on Talbot Street in the heart of St. Michaels (very close to the Winery if you want to visit both in one afternoon!). The Brewery offers a variety of beers for sampling and you can even assemble your own variety pack of beer to take home. Each hand crafted beer is brewed directly on the premises and guests are encouraged stop by and taste their St. Michaels Ale, Knot So Pale Ale, and Magic Hefeweizen, to name a few! Tours are also available upon request.

If you’re planning on staying with us here at Five Gables and you enjoy fine wines and beer, give us a call and we’ll help you plan your visits to St. Michaels Winery and the Eastern Shore Brewing Company! You can also consider booking our “Ladies that ‘Wine’” package, which includes two nights’ accommodations for two people, a 30 minute facial and one hour massage each, and a tour, tasting and gift from St. Michaels Winery. See below for pricing and call us for more information!

King or 2 Twins
Deluxe King
Deluxe Suite