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