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.

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

Golfing in St. Michaels

St. Michaels is famous for its charming main street, its lovely harbor, and peaceful, relaxing atmosphere. Did you know, we are also home to some of the best golfing on Maryland’s Eastern shore! Harbourtowne Golf Resort, located just outside of downtown St. Michaels, boasts a course designed and built by renowned golf course architect Pete Dye. The 18-hole course plays to a par 70 and features many Dye trademarks, including narrow fairways, deep bunkers, neat little ponds and carefully placed mounds to name a few.

Harbourtowne Resort, St. Michaels
Harbourtowne Resort, St. Michaels

The course at Harbourtowne is great for players of all skills and levels. For beginners, it has a practice facility that includes a driving range, bunker area, chipping green and a large putting green. They even offer their guests the option to rent clubs for the day.

Nothing to wear? No worries, the Pro Shop has equipment, apparel and accessories by Callaway, Nike, Taylor Made, Ping, and many more. And the staff is always available for lessons and club fittings.

Harbourtowne is located just a short drive down Talbot Street from Five Gables. It may be cold outside, but it’s the perfect time to begin planning your first golfing getaway of the season. If you are interested in scheduling a golf outing at Harbourtowne during your stay at Five Gables, we’re happy to help. Just give us a call!

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!

Gift Certificates for the Holidays

christmas-presentsThe perfect gift is just a click away! This holiday season, or for any special occasion, treat the special people in your life to a gift certificate from Five Gables. Whether you’re planning to design the ultimate getaway or you prefer to let the recipient use their certificate as they wish, a Five Gables gift certificate is everyone’s perfect gift.

One recent guest is giving their daughter and son-in-law a much-needed escape. Their Five Gables certificate will be good for one “His n’ Hers Romance Package” including two nights accommodation, an herbal bath and 1 hour massage each, and a wine and cheese basket upon arrival. Another is giving a good friend a massage certificate to use for an Aveda Hot Stone Massage in Five Gables’ spa. Today, a visitor to our spa purchased a certificate for her granddaughter to use in buying makeup from the Five Gables Aveda shop – at 16, she can never have enough lip gloss!

As a gift of love or a gift of thanks, Five Gables gift certificates will be appreciated by anyone on your list. Why not make your holiday shopping easy this year? Give us a call, tell us who you’re shopping for, and we’ll suggest the perfect solution! Or, click here to purchase online.

Christmas in St. Michaels

41798_117549961642300_4437697_nChristmas in St. Michaels is right around the corner. Held annually on the second weekend of December, this 24-year tradition is an amazing chance for Christmas Revelers to experience a weekend full of holiday fun!

The weekend will offer a variety of events, some ticketed, some free. All of the proceeds from the Tour of Homes, the Holiday Gala, the Breakfast with Santa and the sale of Collector Ornaments will directly benefit a select number of local non-profits.

Some of the events include:

  • Gingerbread House Display
  • Annual Holiday Gala
  • Breakfast with Santa
  • Christmas Parade
  • Santa’s Wonderland
  • And an Old Fashioned Eastern Shore Christmas Dinner

For more information and to buy tickets for events, visit the Christmas in St. Michaels website: