Boutique hotel holiday rentals near Chesapeake Bay

The Wolbert Room at the Vandiver Inn

Experience the style of a downtown boutique hotel, with the comfort of a country inn. Stay and play in a beautiful waterfront town at the award-winning Vandiver Inn, located just blocks from the Chesapeake Bay in historic Havre de Grace, Maryland. Surrounded by historic homes, museums, close to golf, shopping, antique stores, marinas and water-oriented activities, the Vandiver consists of the Historic Vandiver Mansion, the adjacent Kent & Murphy Houses, the year-round Pavilion and our Gardens.

The Laughing King Retreat, Honeymoon Island Suite

The Laughing King Retreat is an adults only, organic waterfront farm situated directly on the peaceful waters of the 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. For a complete list of all the retreat rooms click the photo of me and Suzanne.

Luxury 1 Bedroom 1 Bath Kingsmill Resort

Welcome to your serene stay in the heart of Kingsmill, a private, gated community nestled along the James River. This one-bedroom guest room offers a peaceful escape. Please note, this listing does not include a kitchen or living room. Inside, you'll find a luxury king-size mattress for the ultimate night’s sleep, a remodeled bathroom with a spacious walk-in shower, HD TV and cable for unwinding after a day out, and your own private porch with Adirondack chairs overlooking the ninth fairway.

Starfish Room - Pool, Hot Tub, Sauna, Spa

No kids, no pets. The Starfish Room is a coastal-themed, split-level luxury bedroom with a private ensuite bathroom. The bedroom has a king-size bed and there's a seating area with comfy chairs. Enjoy the large in-ground pool, the huge jetted spa/hot tub and Himalayan salt sauna. 10 minutes to the Rehoboth Beach boardwalk, just minutes from a wide array of great dining and 130 outlet stores, a short hop to Cape Henlopen State Park, Lewes, Dewey beach and much more. It's time to hit the beach!

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 203 (2nd Floor)

This listing is for The Darwin 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.

The Garden Bedroom at Grandiflora Wine Garden

We welcome all guests who will treat our beloved property with care and respect. The Garden bedroom is on the second story of Grandiflora, our 2-bedroom inn and previous wine bar turning into an occasional event space. Your spacious room overlooks the patio and herb garden with a view of the sunset and the nearby shipyard. In your TV-free room you have your own bathroom (with a tub), as well as a desk for laptop and two comfortable chairs for lounging and enjoying a glass of wine!

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!!

Guest Quarters At The Inn - 205

The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and charming town of North Beach MD. The Guest Quarters are partnered with The Westlawn Inn, an award-winning fine dining restaurant with early-evening live music on the weekends. The five-unit building is in the Arts and Crafts style of the 1920s and boasts special hand-crafted detailed trim work that fits the historic charm of days gone by in the coastal town.

Charming Boutique Haven on C&O Canal! Lock6

Experience the charming boutique setting of The Georgetown House by staying in this lovely private room, ideally situated directly on the picturesque C&O Canal in the heart of Georgetown. Enjoy the area's scenic beauty and diverse activities, attractions, and landmarks. After a day of exploring, return to the room for a rejuvenating stay. ✔ Comfortable Queen BR ✔ Workspace ✔ Bathroom ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Shared Spaces (Kitchen, Porch) See more below!

“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.

★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.