Get a Jump Start on Your Summer 2023 Vacation

Why you should book your 2023 vacation today, and lock in that dream trip next year.

If you’re hoping to get away next year with a group of friends or family, now’s the time to book! Speaking from experience, group vacations are amazing, but they need careful planning! The logistics of getting everyone to the same place, at the same time, can be a challenge. Plus, you all need to be entertained during your trip, something which also requires consideration. That’s why you need to plan your Summer 2023 vacation in Chesapeake Bay early, and allow yourself the time to prepare the best trip ever!

A Summer 2023 Vacation in Chesapeake Bay is Ideal for Anyone

At Tidewater Vacations, we take most of our group bookings a year in advance. Be that for a group of buddies getting together for a few days of grilling and chilling. Or a vacation for the extended family full of pool time and adventures. Our vacation homes are hugely popular with all sorts of holidaymakers. But the one thing they have in common, is that the most successful ones get in quick, and leave their deposit with us early. Knowing that their chosen date, the only date they can all do, will get booked up if they don’t act fast.

Only Need to Pay a Deposit Today

When choosing one of our Chesapeake Bay vacation properties for your Summer 2023 stay, you only need to pay a deposit today. There’s no need to pay the full amount until further down the line. Meaning you’ll have plenty of time to group save with your friends, or work towards a vacation budget with your family. All the while planning what amazing adventures you’re going to have in Chesapeake Bay, one of the most beautiful parts of the country.

Plan the Dream Trip with Our Expert Team

By getting in touch early, and providing our expert team with your chosen date, you’ll be able to view our full selection of stunning vacation homes – before they get snapped up! We have a wealth of properties, with countless different configurations. Suitable for almost any gathering size. But they are popular. Leave it too long, and we might not have the perfect home left available for your family. That’s why we encourage you not to leave it, and get in touch with our team direct, today. They’ll be able to give you a private tour of our luxurious waterfront homes in Chesapeake Bay, and find you the perfect place for your Summer 2023 vacation.

Make Summer 2023 One to Remember

Give yourself, and your friends or family, something incredible to look forward to next year! We’ve all had a rough couple of years, and now finally we can properly be together. Celebrate that, and embrace the ones you don’t get to see as often as you’d like, by arranging a dream Summer 2023 trip to Chesapeake Bay together. And let us at Tidewater Vacations take care of the rest.

Ready to start planning your Summer 2023 vacation? Head over to our vacation homes page. Where you’ll find extensive listings of our premium rentals with up to 6 bedrooms, in various styles and some with a few hidden surprises!

If you would like to book any of our properties, please do so via our online booking platform, and if you require any further assistance, please do not hesitate to get in touch with our team.

Which Chesapeake Bay Rental is Best for Your Vacation

Choosing a vacation rental in Chesapeake Bay offers so much more than your typical B&B or hotel stay. But which type of property is right for you?

If you’ve never stayed in a Chesapeake Bay rental before, or maybe this is your first vacation to the area – you’re in for a treat! The Bay stretches out for roughly 200 beautiful miles and is mostly bordered by Maryland and Virginia. It’s a stunning, picturesque part of the country with a wide variety of pretty villages and areas of interest to explore. There are also plenty of different locations to call home while on a Chesapeake Bay vacation, including rental houses with private pools, pet-friendly facilities, and a variety of amenities to make your stay supremely pleasant and comfortable.

But with so many vacation rental options available in Chesapeake Bay, how are you supposed to know which one to pick?! That’s where we come in. At Tidewater Vacations we are very proud of our unique collection of rental homes. Properties that offer serenity, style, and comfort in a wide variety of sizes and styles. Today, we thought we’d share just some of these rental opportunities with you, along with the type of guest they might appeal to.

  • Which Chesapeake Bay Vacation Rental is Right For You?

  1. Combsberry of Oxford

We’re starting off with one of the larger vacation rental properties we have here in Chesapeake Bay, Combsberry of Oxford. This adorable house on an historic estate dates back to 1730 and is blessed with 30 acres of manicured gardens, peaceful waterfront and picturesque farmland.

This stunning property is large enough to sleep 12 across its 6 luxurious bedrooms, making it ideal for extended families looking for a long weekend away. Plus, you can even bring your furry friends, as this property is pet-friendly.

Just imagine sitting on your private deck in the evening, surrounded by loved ones, and watching the sun go down with a glass of wine. Idyllic! And during the day when you’re not exploring the surrounding countryside, you and your crew can enjoy the stunning outdoor pool.

  1. Savanna

Savanna is one of Maryland’s oldest and most picturesque rental homes. It has sat proudly on the banks of the Miles River in Talbot County since 1659, and has certainly evolved through the years. Now, this beautiful home celebrates its storied past with a decor that’s reminiscent of its major moments in time. The perfect property for those who love to step back in time, while also feeling like they have all the modern conveniences.

These contemporary amenities include en-suite bathrooms in three of the five bedrooms, an outside kitchen and a brand-new pool with decking area. Perfect for those warm summer evenings. This Chesapeake Bay vacation rental would be ideal for a family, or even a bridal party preparing for the big day! It would make the most luxurious pad for some pre-wedding pampering.

  1. The Beach House

Treat you and yours to that celebrity lifestyle during your Chesapeake Bay vacation, by staying in this glamorous waterfront rental. With its own private beach, you’ll feel like the evening’s sunset is exclusively yours while you sip champagne, and lounge in the sand, or reside on your expansive balcony overlooking the sea. A view which can also be enjoyed via huge windows both upstairs and downstairs, offering uninterrupted viewing of the beautiful scenery all around.

The Beach House can sleep 8 across 4 bedrooms, making it ideal for groups of friends who want a fun, luxury getaway, complete with private pool, dock, and BBQ area.

  1. Aspen on the Tuckahoe

Take the kids away for an adventure of a lifetime at Aspen on the Tuckahoe, a unique Chesapeake Bay vacation rental tucked away among towering pines. Your little ones will love this place from the moment they arrive, marvelling at the fun bridge that guides you into the property. When inside, you’ll find a wonderland of fine wooden detailing, alongside chic contemporary decor and all the space you’ll need for a relaxing stay.

This stunning home benefits from enchanting views of the river, which can be enjoyed either by the large windows, or via the extensive decking area. Which is also features a BBQ and relaxed seating area. The perfect place to fish, swim, or moor your boat. And when you want the kids back inside, they’ll be happily entertained in the luxurious games/family room, complete with ping pong table and movie theater space.

Have you found the perfect Chesapeake Bay vacation rental? No! Don’t worry, we have many more amazing properties, and they can all be viewed via our vacation homes page. Where you’ll find extensive listings of premium rentals with up to 6 bedrooms, in various styles and some with some hidden surprises!

If you would like to book any of our properties, please do so via our online booking platform, and if you require any further assistance, please do not hesitate to get in touch.

Saint Michaels Vacation Rentals Planning Guide

If you are looking for a charming place to vacation that’s off the beaten path, look no further than Saint Michaels, Maryland. This small town is located on Maryland’s eastern shore and is a true hidden gem. Called the Hamptons of the Chesapeake Bay, Saint Michaels is known for its beautiful scenery, quaint shops and restaurants, and its friendly locals. 

A vacation in Saint Michaels is the perfect way to relax and escape the hustle and bustle of everyday life. Here’s your guide to Saint Michaels vacation rentals and other helpful planning tips.

Why Vacation in Saint Michaels?

Travelers from all over love Saint Michaels’ historic charm. The town was founded in 1634 and has preserved much of its original architecture. Visitors can stroll down streets lined with 18th and 19th-century buildings, including the old Talbot County courthouse.

The town also brings you closer to nature. There are also several parks and nature trails in the town, making it a great place for outdoor activities. It’s a great place to disconnect and unwind if that’s your goal, but there are also plenty of opportunities for adventure.

Things to Do in Saint Michaels

Saint Michaels gives you tons of ways to indulge in your vacation time. Start with a trip to the historic downtown, which is brimming with cafes, coffee shops, bistros, boutiques, and the Saint Michaels farmer’s market. 

 The Chesapeake Bay Maritime Museum is located in Saint Michaels and offers visitors a chance to learn about the area’s maritime history.

Thanks to its close proximity to the water, you can also take river boat cruisers and spot dolphins, ospreys, and other wildlife. The river and its many creeks and waterways are also great places for kayaks and SUPs. 

Depending on the time of year, you might also pop in on one of Saint Michaels’ many festivals. Chocolate Fest, Wine Fest, Brew Fest, and Oyster Fest are fan favorites that locals and travelers alike look forward to.

Where to Find Saint Michaels Vacation Rentals

As you’re planning your vacation to our charming town, one item on your to-do list is to explore Saint Michaels vacation rentals. Travelers typically prefer the cozy, homey appeal of a vacation rental instead of a traditional hotel (which you won’t find many of here). Finding a luxury vacation home gives you all the comforts of home while you travel, puts you in close proximity to the waterfront and all the best things to do, and creates a more personalized travel experience. 

At Tidewater Vacation Rentals, we specialize in Saint Michaels vacation rentals to give you the best home-away-from-home experience. We feature some of the most stunning luxury homes for short-term rentals in the area, complete with picturesque waterfront views, swimming pools, and plenty of space for couples and large groups alike. 

Contact us today for availability information and let us help you plan the perfect Saint Michaels vacation!

What to Expect from a Luxury Vacation Rental on the Chesapeake Bay

luxury vacation rental on the chesapeake bay

A break from work or everyday life relieves stress, improves productivity, and gives you the me-time you deserve. One of the best ways to take the break you deserve? Doing it on a luxury vacation rental on the Chesapeake Bay

Staying at a breathtaking luxury vacation rental on the Chesapeake Bay is a once-in-a-lifetime opportunity that you and your family will remember forever. 

Not convinced yet? No problem! 

This post outlines the top three things you can expect from a one-of-a-kind rental on the Chesapeake Bay. 

3 Top Things to Expect from a Luxury Vacation Rental on the Chesapeake Bay

Here are the top three things you can expect from a luxury vacation rental on the Chesapeake Bay:

Luxury Amenities

From waterfront rentals to stunning manors, luxury vacation rentals on the Chesapeake Bay have it all.

We don’t even have to exaggerate things because the reviews and pictures say it all.

In particular, luxury vacation rentals on the Chesapeake Bay have relaxing pools, pet-friendly areas, fireplaces, docks, and more. 

Imagine staying at luxurious vacation homes after a hard month at work. Think about being kissed by the sun as you swim with your loved ones. Looks amazing, right? 

Well, you can stop imagining now. Make your dream vacation come to life by renting luxurious vacation homes on the Chesapeake Bay. 

Spectacular Location

If you want to take a vacation that will make you say, “Everything’s worth it”, you better not skimp on the location.

Whether you’re going with your special someone, family, or friends, luxury vacation rentals on the Chesapeake Bay will take you to your happy place.

The vacation homes also offer views that blow everyone away. 

Want to enjoy nature and lake views at the same time? The Prairie Wind vacation home is ready for you.

Want to simply relax on the deck, see the lake, and jump in the pool after? Check out The Papillion vacation home. 

On top of that, luxury vacation rentals on the Chesapeake Bay are near stores, restaurants, and tourist spots. So, if you want to go around, go ahead. Delicious food, beautiful spots, and Instagrammable pictures await you. 

Word-Class Customer Service

Spoiler alert: Luxury vacation rentals on the Chesapeake Bay offer just as much luxury in terms of customer service.

After all, a vacation won’t be perfect if a receptionist or housekeeper nags at you, right? 

From booking to arrival and departure, you can expect nothing but the best from a luxury vacation rental on the Chesapeake Bay.

Our staff has been trained to offer stellar customer service and make sure that your trip goes smoothly. On top of that, they are trained to keep our vacation homes COVID-free so you get the peace of mind you deserve.


Luxury vacation rentals are the hidden gems of the Chesapeake Bay. From luxury amenities to world-class customer service, Tidewater Vacations is here to make your dream holiday come true.  

Ready to enjoy your once-in-a-lifetime escapade to the Chesapeake Bay? Call us at (443) 786-7220 now!

Property Spotlight: Chez Bonheur

Chez Bonheur is a 6 bedroom property that sleeps 12 and features a dock and a boathouse!

Only minutes from the famous historic “Chestertown”, this magnificent 1000 acre estate is both a wildlife sanctuary and arboretum, with hundreds of mature specimen trees and acres of woods and farm fields. The contemporary style home is just a fabulous family retreat offering traditional, yet sophisticated and extremely comfortable accommodations.

Sited perfectly high above the river, this spectacular home offers wonderful views of the sun setting over the water and quiet evenings to listen and watch the eagles and osprey, while living in a very luxurious environment. This home is ideal for a family vacation away from it all.

The entrance to the farm is quite breath taking – a very long, tree lined driveway winds past a large duck pond and then there it is – you drive through large iron gates into a bricked courtyard which is planted with flowers and herbs. The huge wooden front door is made of Cherry and the first thing you notice is the wonderful light streaming through the windows. The entrance foyer is phenomenal with the tasteful artwork and wood carvings. “Chez Bonheur” has the view we all dream of – look out through the large sliding doors leading from the dining room/living room area out to the wide water views.

You are now safely tucked away from the crowds and let’s get you settled in. One walks into the dining room which is open to the living room. There is a large deck off the living room facing the water. Views, views, and more water views ! Just to off your left you will find a bright and airy, open plan kitchen and casual dining area with a sitting area around a fireplace which leads out to the screened porch. What a treat to cook and entertain in this grand area overlooking the water. There is a master bedroom with queen bed with en suite bathroom on the first floor too!

Upstairs you will find another master bedroom with en suite bathroom, a guest bedroom with a queen bed with en suite bathroom, a small bedroom (with the castle painting) with a twin bed, another bedroom with a set of bunk beds and en suite bathroom and then ….. the incredible small peoples play room with all sorts of fun toys. You are welcome to use the personal assistant’s apartment suite, which has an open plan living/bedroom with Queen bed and its own bathroom.

Now you can sit back, get the BBQ going, have a cocktail, swim in the pool and watch the sun set while the family catch crabs off the dock or catch a fish for dinner! This is bald eagle country so don’t leave those binoculars at home! Bring your boat or kayak – great boat house and dock too!

The 1000 acre estate is just 5 miles outside Chestertown which is well known for it’ fine dining restaurants, lots of casual restaurants too, great eclectic little shops, lots of antique stores and a golf course. You can also do day trips to Annapolis, Rock Haul, Centreville and St Michaels. So come on down and enjoy “Chez Bonheur”!

Check out the property listing @

and give us a call to book today!

(443) 786-7220

Visitors to the Eastern Short of the Chesapeake Bay Will Find

A unique destination in Talbot County, Maryland. Since people have been living, working, and visiting here for about 340 years, we probably can’t claim this is a “recent find.” What we can claim with great certainty is that Talbot County offers the “cure for the common vacation.”

We have heard it said by some that Talbot County is the new Hamptons. ENTREE disagrees with that notion. We don’t think that it is the “new” anything, nor does it need to be. Besides, the Hamptons are so last century. The Chesapeake, the eastern shore and Talbot County have their own distinct identities which, while similar to the Hamptons in some ways, are vastly different in most others. For example, we don’t feel deprived at all by missing out on crowded, overpriced restaurants, negotiating hours of congested traffic or locals who would just as soon see you gone.

Our first trip to Talbot County was in winter and it was exceptional. We were hooked from day one. There were fewer outdoor activities but there was a little snow on the boats and the harbors and the beauty of the countryside was magical. Recently, we returned in the summer and found a completely different experience. This is without doubt a destination for all seasons.

Getting to Talbot County is relatively simple. It is close to several major east coast cities. Washington, D.C., for example, is only a one and a half hour drive. The area is steeped in the history of the United States. Reading that history, it seems that most of what we went through as a nation, from the pilgrims to several wars, to slavery, abolition and building the country, happened in and around Talbot County. A great read, especially if you plan a trip to the area, is James Michener’s novel, CHESAPEAKE.

Today, it is all about recreation, creature comforts and spectacular places to live. Not surprisingly many activities are on the water but a good many are on land-biking, hunting, golf. You can forget about not having enough to do. It seemed to us that every week there was another festival or production, whether music, art or theater. That, of course, is what we referred to as the cure for the common vacation.

There are four principal towns in Talbot County: Easton, St. Michaels, Oxford, and Wightman. They are close together and each is a blend of the old and the new but each are unique in their own way. Three-hundred-year-old Easton centers the county. Easton is the seat of county government and is the more urbanized of the four cities. It boasts the best shopping, nightlife, museums and cultural centers.

Foodies rejoice about the incredible number of great restaurants. There are twelve restaurants in Talbot County in the 2011 edition of the Zagat Guide and that includes Washington D.C. and Baltimore. The Bartlett Pear Inn, described as an upscale American bistro, was one of our favorites. This treasure would hold its own in any of the serious food cities of the country. It has received accolades in Zagat and other publications and is richly deserving of them all. Lunching at The Tidewater Inn is a must. Walk down the street to check out what is on the bill at the Avalon Theater.

The city of Oxford just south of Easton on the Tred Avon River tends to be more historical. It dates back to 1683 and is still one of the best places to live. Naturally, it has a great restaurant: the Robert Morris Inn.

Robert Morris, for those of us who slept through American history, was one of the signers of the Declaration of Independence. The new owners are renowned Chef Mark Salter and his partner Ian Fleming (no, not that one), both of whom recently distin guished themselves at The Inn at Perry Cabin. The Tred Avon Dining Room is in the original 1710 public rooms and offers Chef Mark’s signature dishes plus a wonderful wine list.

St. Michaels may be the best known of the four. It is famous as a historic maritime center as well as a commercial hub with dozens of cute little shops, bistros and galleries. The Maritime Museum, both a museum and a classic boat repair yard, is one of the highlights of the entire area.

The history of the Chesapeake is, to a large degree, the history of ships and sailing. That history lives at the Maritime Museum. Another highlight of St. Michaels, of course, is the spectacular Inn at Perry Cabin for food, lodging and waterfront beauty. If the weather is warm, we would sit outside for lunch at St. Michaels Crab and Steak House. Not only is the seafood tops but you can quiz owner Eric Rosen on anything to do with sports teams in Philadelphia.

Tilghman Island is a water lover’s paradise. It is home to the legendary fleet of lightning fast working sailboats called the “skipjacks.” It is also where most of the “watermen” lived.All the towns of Talbot County are unique but Tilghman is the most original. The Tilghman Island Inn is a fine choice for a great meal and lodging right on the water.

Accommodations in Talbot County are many and varied, including inns, bed & breakfasts, guesthouses, full service resorts, hotels, cottages, and rental homes.

If you are not ready to build or buy then you want to contact Angela Spence at Tidewater Vacations to see what living the good life on the Chesapeake is really like. Angela has taken vacation rental houses to another level. Her properties, on the eastern shore, are some of the finest estate homes in Talbot County and run from two to six bedrooms. Every imaginable amenity is usually included—even a boat if you would like one brought to your private dock. This is an experience to share with your family and/or friends that will be unforget- table. Check out her website at or call (410) 745-5255.

As we mentioned earlier, there is no shortage of activities in Talbot. It is a good bet that you will run out of time before you run out of things to do. One adventure not to miss is a sail with Captain Jeff Mathias aboard the Lady Patty, which is docked on Tilghman Island. Shopping in the area deserves much more coverage, but at least check out The Troika Gallery and Gatsby’s in Easton.

Talbot County has an office of tourism which is always a great help. and (410) 770-8000.

Laps of Luxury

Can’t afford that multimillion-dollar Talbot County dream house? At these nine palatial estates, you can live the good life for a week at a time.

  1.  Blowing In The Wind

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay, Prarie Wind
If your tastes tend toward contemporary, there are few more stunning homes on the Bay than Prairie Wind, located just outside of St. Michaels. Designed by Washington architect Suman Sorg and Associates and landscaped by fellow D.C.’er James van Sweden, Prairie Wind looks like a home straight out of last’s month’s Architectural Digest. Three attached wooden buildings house a central living area with funky modern furnishings—chairs and loveseats come in vibrant reds, yellows, and oranges. Views out of the two-story, floor-to-ceiling windows are of tall reed grass and sunsets over the Bay. (Heck, even the view from the bathtub is stunning.) The adjacent buildings house two master bedrooms and full baths. If you can ever tear yourself away, a circular swimming pool surrounded by more reed grass awaits outside, as do several footpaths leading down to a private Bay-side beach.—J.S.

Price tag: $5,000 per week

Book it: 410-745-5255

2.  Green Acres

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay, Millwood Manor.
Ah, the pleasures of estate life: just you, the wildlife, and a host of groundsmen, all of whom are charged with maintaining Millwood Manor’s 100 acres. Take a jog along the miles of mowed paths, most of which border the Tred Avon River or stop and smell the roses blooming in the six-acre garden. The three-bedroom, circa-1800 property—complete with a two-bedroom guest cottage, tennis court, and resident pheasants—was occupied by Owen Wilson while filming Wedding Crashers. But it’s anything but high-profile thanks to its mile-and-a-half, tree-lined driveway that keeps the estate wonderfully hidden from the rest of the world.—K.B.

Price tag: $8,000-$10,000 per week

Book it: 410-745-5255

4.  Sweet Dreams

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay, Sycamore Llanding.
Chandeliers, chaises, and 600-thread-count cotton sheets. What more can you ask for in a master bedroom—except, of course, a fireplace, four-poster king-size bed, and plush carpet? Sycamore Landing has these spoiling details—and more. Modern-day princesses (and princes) will also appreciate the suite’s walk-in closet, and great view of the Miles River. The circa-1659, five-bedroom property is one of the oldest estates in the county and is a favorite haunt among Washington, D.C., politicos, who likely prefer the library, complete with grand piano and deep leather sofas. Brandy and cigars before retiring, anyone?—K.B.

Price tag: $5,000-$7,000 per week

Book it: 410-745-5255

6.Thomas Jefferson (Would’ve) Slept Here

If you’ve ever wanted to stay the night at Thomas Jefferson’s Monticello—but the guards kicked you out at closing time—then book San Sano, located between Easton and St. Michaels. The regal, multicolumned entryway clearly shows T.J.’s influence, and pulling up along the white gravel lane lined with London plane trees and loblolly pines gives guests a reception worthy of a president. (Or someone with pockets just as deep.) The cream and beige five-bedroom interior is decidedly more modern and accented with stone—the enormous dining room marble fireplace looks as if it could burn a sequoia. Spend your days exploring the 146-acre grounds, five of which accommodate a vineyard, which supplies grapes to Little Ashby Winery nearby. The estate’s name is a nod to a small Italian town, and if you try hard enough while sipping Campari and soda by the home’s enormous swimming pool, you just might convince yourself that those Bay breezes are really


Price tag: $8,000 per week

Book it: 410-745-5255

7.Docking Station

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay | Kirkland Manor
You can pull your Bay cruiser right up to the deep-water dock at Kirkland Hall Manor, a sprawling 1920s, white-pillared Georgian estate, located outside of St. Michaels. Unload your baggage at the private boat house and then stroll across the broad lawn (pass by the swimming pool) to the estate, where the nautical décor theme continues. Inside, there are six bedrooms—five of which have their own private baths and sitting rooms—and a dining room table long enough to accommodate nearly everyone on board. If the weather is iffy, relax with a hardback in the library, tickle the ivories on the baby grand piano, or retire to the game room for a gentlemanly poker match.—J.S.

Price tag: $12,000 per week

Book it: 410-745-5255


Hidden Gem on the Chesapeake Bay

Though the Chesapeake Bay area of Maryland is home to all variety of quaint coastal villages, St. Michaels is a true find. Tiny and loaded with charm, it boasts a rich maritime heritage, eclectic boutiques, historic inns, antique shops, art galleries, spas and all manner of eateries. There is even a local brewery and winery. However, it is the magnificent harbor-front locale of the surrounding Miles River that will captivate you. Whether you are sailing, yachting, kayaking, fishing or planted on terra firma and feasting on plenty of fresh blue claw crab, historic St. Michaels is a seaside delight.

Located on the eastern shores of the Chesapeake about 10 miles from Easton, Maryland, St. Michaels (about 4hrs south of Manhattan by car) is known as “The town that fooled the British.” It is said that late one night during the War of 1812, residents placed lit lanterns high up in the trees and on ship masts so the cannons of the invading Brits ended up overshooting the town. That inventive spirit survives today.

St. Michaels’ proud maritime history includes shipbuilding, oystering and crabbing, all of which are beautifully represented at the Chesapeake Bay Maritime Museum ( Featuring 15 buildings full of interactive exhibits spread across 18 pristine waterfront acres, the museum celebrates the area’s rich history and culture—and don’t miss exploring the 1879 Hooper Strait Lighthouse. The museum will also host the Chesapeake Folk Festival July 23rd, 2011.

Talbot Street is the main drag through St. Michaels and features dozens of beautiful Victorian and Colonial storefronts. You will not find a Starbucks here but you can visit Ava’s Pizzeria for her wood-fired gourmet pizzas; Big Al’s Market & Seafood for steamed crabs (eat in/take out); Rupert’s London Bar & Tea Rooms for its famous crab soup; 208 Talbot Restaurant & Wine Bar for New American cuisine (try their new 208 Burger for a more casual vibe) or the Carpenter Street Saloon for the “coldest draft in town.”

If you plan to travel in April, the shops along Talbot Street throw open their doors for the annual St. Michaels “WineFest” celebration featuring local vintages, gourmet goodies and more. This year’s festive fun runs from April 29th through May 1st.

For your traditional crab feast, make haste to the harbor where waterfront dining is de rigueur during the warm weather. Bob Pascal’s St. Michaels Harbour Inn, Marina & Spa offers dynamic indoor/outdoor views. If you don’t care for crab, do not let on; just order the chef’s English fish & chips—a massive portion fried to perfection. Other harbor favorites include the Crab Claw Restaurant, Crab & Steak House and Town Dock Restaurant. Come hungry and don’t spare the Old Bay seasoning.

For shoppers, there are all sorts of specialty boutiques with names as quirky as their inventories, like A Wish Called Wanda, Fine Old Posters and Flying Fred’s Gifts for Pets. Antiquing and art enthusiasts also have a number of galleries and shops to choose from.

There is no shortage of accommodations in St. Michaels. The Inn at Perry Cabin ( is consistently rated as a top luxury hotel, which it shows in everything from staff to services. Designed in the Colonial style and loaded with amenities, it expertly blends modern and period décor with classic nautical motifs. Also on the grounds is the award-winning Linden Spa.

The Five Gables Inn and Spa ( is located right in town and is steeped in charm while the aforementioned Bob Pascal’s St. Michaels Harbour Inn, Marina & Spa ( is a full-service resort with 46 waterfront suites and 52 slips at its marina. Golfing enthusiasts might want to stay just north of town at the spacious Harbourtowne Golf Resort (, which features an 18-hole Pete Dye designed course.

St. Michaels is well known as a yachting destination—you’ll see sailing vessels of every shape and size fill the harbor and the Miles River. If you are a true boating enthusiast, time your visit for the Antique & Classic Boat Festival, June 17th-19th 2011, at the Chesapeake Bay Maritime Museum—it’s the largest in the Mid-Atlantic region. Meanwhile jet skis, kayaks, sail boats, power boats and tip-to-toe fishing gear are all available for rental. If you prefer to kick back and let someone else be the captain, there are sailing tours, paddle boat tours or you might take a cruise aboard the Patriot—a St. Michaels institution for over 40 years.

No matter what you plan for your St. Michaels visit, it will be easy to kick back and relax. For more information visit the Talbot County Tourist Board,

Southern Living Magazine ranks St. Michaels in the top 3 “Best Small Town Getaways”!

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake BayChesapeake Bay Magazine’s readers and web community have cast their votes in their annual “Best of the Bay Survey”, and St. Michaels was for The Best Town for Families, Best Town for Foodies, Best Town for Nightlife, Best Town for Sightseeing and The Best Town For Inexpensive Docking!