Boutique hotel holiday rentals near Chesapeake Bay

Classified Moto - The Frank Room

Since 2009, Classified Moto has been building unexpected custom bikes for people all over the world. And now, we’ve outfitted our new secret headquarters with six guest rooms that are just as fun and surprising as our bikes. Keep reading for more about Classified, but first, the FRANK ROOM has caught your eye. Let’s talk about it. Frank, as in brutally honest? Frank, as in frankfurter? No, Frank is probably our second most famous custom bike — a 2007 Triumph Speed Triple we built years ago.

Water View with Beach, Walk to restaurants & shops

Sandaway Suites & Beach is located in the historic district of Oxford, MD where you can walk to several restaurants and shops. With stunning waterfront views and a private sandy beach on the Eastern Shore of MD rests our boutique hotel. We invite you to stay in one of our beautifully restored water view rooms. Experience in-room comforts and in-town conveniences. Take a day trip to St. Michaels, Easton, or Cambridge. At the end of the day, see an awesome sunset at Sandaway's private beach.

Armistead House - Room 302 (3rd Floor)

This listing is for The Edison Room at the historic Armistead House, which offers a total of 5 separate bedrooms. It is conveniently located within a short two block walk to the Colonial Williamsburg Historic District and its iconic Duke of Gloucester Street, museums, shopping and restaurants. It's also a short walk to The College of William & Mary and the Williamsburg Train Station. Leave your car in our free private parking lot and enjoy the short stroll to the heart of Williamsburg.

“Pretty In Pink” at the Terry House !

This stylish and unique place sets the stage for a memorable trip. We purchased The Terry House, in January of 2023 and have been renovating the home for the last two years. This room is on the 2nd floor inspired by Jackie Kennedy featuring antique and historic art work. This private room is spacious, with a queen bed as well as private baths and a mini fridge in the room. There is a common area space called the parlor room on the first floor with a Keurig and microwave for you to use.

The Laughing King Retreat, Cobb Island Suite

The Laughing King Retreat is an adults-only, organic waterfront farm situated directly on the peaceful waters of Chesapeake Bay. Your private guest suite will enjoy breathtaking sunrises and sunsets, private waterfront pool, private beach, hiking trails, miles of soft sugar sand sandbars to explore and enjoy. Private Chesapeake Bay water access for boating, swimming, paddle boarding, fishing or just soaking. Dig for clams, collect wild oysters, or just sit and marvel at the beauty.

Maurice Inn and Fusion Bistrot Yellow Room

Beautiful Boutique Inn in beautiful Onancock. Close to everything with a fine dining fusion restaurant on premises offering fresh local produce prepared with international flair. Nearby is Onancock Wharf where you can kayak, paddle board or take a trip to unique Tangier Island in the middle of The Chesapeake Bay. A short drive away is international tourist destination Assateague National Wildlife Refuge with its beautiful beach and wild ponies. Come unwind for a day or a week!!

“Out to Sea” at the Terry House !

The Terry House, a Federal Townhouse circa 1860, is located in historic New Castle, Delaware. This room is on the 2nd floor, featuring a historical nautical theme in one room and historical classic cars in the other room. This suite features, a queen and a full beds as well as private baths and a mini fridge in each room. There is a common area space called the parlor room on the first floor to work, hangout, or play games. ** Not serving breakfast at the moment.

The Garden Bedroom at Grandiflora Wine Garden

Welcome to the Garden bedroom on the second story of Grandiflora! We are a vegetarian natural wine bar and 2-bedroom inn located in the heart of Chelsea. Your spacious room overlooks the patio and vegetable garden with a view of the sunset and an intriguing view of the nearby shipyard. In your TV-free room you will have your own full bathroom (with a tub), as well as a desk for laptop work and two comfortable chairs for lounging and enjoying a glass of wine!

★Historic Harrison Room -The George of Old Town★

The William Harrison room is a great place to call home while you're visiting Old Town. On the third floor of the George, this room can accommodate up to 2 guests with its lush velvet headboard on king bed with small balcony and exterior circular staircase. The en suite bathroom has a large walk-in shower and white subway tile and plush towels. Views of the back patio area and surrounding buildings.