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.

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 @ https://tidewatervacations.com/vacation-homes/chez-bonheur/

and give us a call to book today!

(443) 786-7220

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 (cbmm.org). 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 (perrycabin.com) 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 (fivegables.com) is located right in town and is steeped in charm while the aforementioned Bob Pascal’s St. Michaels Harbour Inn, Marina & Spa (harbourinn.com) 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 (harbourtowne.com), 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, tourtalbot.org.

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!