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.

Photographs by: William Wilhelm | williamwilhhelm.com

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