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.

Let It Snow, Let It Snow, Let It Snow!

Oh the weather outside is frightful, but the fire is so delightful…

The cold weather of the last few weeks has finally delivered the first snow of the season to St. Michaels. The town is lovely covered in its blanket of white, so why not escape to Five Gables and enjoy a relaxing getaway in one of our lavishly renovated rooms?

Winter is the perfect time to take advantage of all that Five Gables has to offer, including:

  • Fireplaces in every room
  • The only heated, indoor pool in St. Michaels
  • A full service Aveda spa
  • A sauna and steam room to banish the winter chills!

While we have plenty for you to do inside our cozy Inn, should you choose to venture out you’ll find yourself in the heart of picturesque St. Michaels, within walking distance of fine dining, boutique shopping, and the harbor for which the town is known.

This winter, we’re offering fantastic mid-week rates. With rooms at $99 a night and suites at $149 a night, a midweek getaway has never been so tempting!

Thanksgiving in St. Michaels

St. Michaels is a popular destination during the summer months because of it’s location on the Eastern shore, but did you know that it is just as beautiful throughout autumn and winter?

St. Michaels is so quaint and beautiful during the fall season, but if you haven’t had the chance to experience it yet, time is running out! Thanksgiving is right around the corner and there is absolutely nothing like spending the holiday season in a small, waterfront town.


Why not spend the post-Thanksgiving weekend with us? Avoid the madness of Black Friday by doing all of your shopping in our charming little town.

Many of our local retailers will be offering Black Friday specials, so you can receive the holiday discounts without all of the insanity you would find in a crowded mall.

We have plenty of openings for the weekend of Thanksgiving, but we expect them to go fast, so be sure to book sooner rather than later!

Call us today!

Amenities Galore at Five Gables Inn!

We are proud to offer a wide variety of amenities to match any of our guests needs. The most popular summertime amenity is the complimentary bikes we provide for our guests to explore St. Michaels with. All of our rooms also come with air-conditioning for the summer and fireplaces for the winter. For our guests relaxation we provide Aveda spa products in our bathrooms, each outfitted with a whirlpool tub. The Inn also has a seasonally heated indoor swimming pool, sauna and steam room, as well as 4 pet friendly rooms, so that your dog can stay in comfort with you in our well appointed guest rooms. We are happy to help our guests schedule events for the weekend to make sure they see all that St. Michaels has to offer! Visit us today at to book your weekend getaway!

3rd Annual Chesapeake Bay Maritime Museum Folk Festival

Join us for a weekend of great folk music on the water! This Saturday, July 31st is one of our favorite events of the year in St. Michaels. Our neighbors, the Chesapeake Bay Maritime Museum, are throwing their 3rd annual Folk Festival to, “celebrate the Bay’s people, food, music, work and traditions.” This fantastic event includes boat rides, maritime demonstrations, and even includes events for kids.  The festival runs from 10am to 5pm, which leaves plenty of time to relax and explore St. Michaels. Our Inn is conveniently located in the heart of historic St. Michaels, a short walk to the Maritime Museum and to shopping and restaurants. Take out our complimentary bikes for a Sunday afternoon picnic, the perfect end to a great weekend! Visit to book your weekend getaway.

Holy Smoke Maryland State BBQ Championship in Easton, MD

Join us this Saturday and Sunday on Marlboro Ave in Easton for the 1st Annual Holy Smoke Maryland State BBQ Championship! Admission is just $3, free for kids 10 and under. When you’re tried some of the states best BBQ enjoy some live music by Coffey Anderson, have the kids play on the free air bounce and carnival rides! Even watch a twinkie eating competition! After a day full of BBQ and fun, relax with us in our indoor pool or stop by our Aveda spa for a massage or facial. Make sure to burn off some of that BBQ by taking our complimentary bikes for a spin around St. Michaels! Visit for more information regarding the event. The St. Michaels Community Center is presenting Dan Goggin’s Broadway smash hit “Nunsense” at St. Michaels High School, Thursdays, July 22 & 29 at 7 pm, Fridays and Saturdays, July 23, 24, 30 & 31 at 8 pm and Sundays, July 25 and August 1 at 2 pm. Between the BBQ and the show you will have a jampacked weekend of good food, fun and entertainment on Maryland’s eastern shore!

Featured Package: Spa and Sail

Looking to escape to the Eastern Shore for two nights of relaxation and sailing? Look no further than our special summer package, Spa and Sail. This package includes two night accommodation, two 1-hour massages in our Aveda Spa, a two hour sail plus a $50 gift certificate to The Crab Claw! Package available weekends or weekdays. Please contact us at to reserve. While you’re not on the water explore all St. Michaels has to offer. Visit us between July 19-25 and enjoy Plein-Air Easton, the outdoor painting competition hosted by the Avalon Make sure to check out the Hundred Studio Tour to check out the artists work during the competition.

Historic St. Michaels

Aside from being an amazing place to get away, St. Michaels, Maryland has a rich history dating back to the 1770’s. Many of its historic attractions have been preserved and put on exhibit for the public to enjoy. Any historic boat lover will appreciate the Edna E. Lockwood, a Chesapeake Bay bugeye, which is the last working oyster boat of her kind. Built in 1889 on Tilghman Island, she is on display at the Chesapeake Bay Maritime Museum. The St. Michaels Historic District is a great area for any history buff to wander around, taking in the historic integrity of the buildings. Make sure to see The Cannon Ball House, which has a cannon ball embedded in the house from an attack during the war of 1812. Come spend the weekend with us and take in all the history St. Michaels has to offer!

There are so many ways to enjoy Memorial Day Weekend in St. Michaels!

If you are headed to Maryland’s Eastern Shore this Memorial Day you are in for a treat, there are so many ways to get out and enjoy the 3-day weekend! Memorial Day is the first summer kickoff, so why not get out and enjoy a crab feast at one of our local crab houses, or take a bike ride along the rivers of St. Michaels. On foot there are so many restaurants, shops and galleries to explore on Talbot Street. Celebrate Memorial Day on Sunday with the Three Penny Opera playing on the Patriot Charter Boat. Details can be found at And when all the fun is over, stop by our Aveda Spa for a facial or a hot stone massage. What better way to kick off summer?!