Boutique hotel vacation rentals near Chesapeake Bay

The Donahoo 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, and close to golf, shopping, antique stores, marinas and water-oriented activities, the Inn consists of the Historic Vandiver Mansion, the adjacent Kent & Murphy Houses, the year-round Pavilion and our Gardens.

Beach Bum Inn Beach Bum Inn 3rd Cityview 2 D

Best Rates at Ocean City Motels & Hotels Beach Bum OC offers hotels, motels, apartments, and vacation rentals in Ocean City, Maryland. Be sure to book directly with us by phone or on this website to avoid 3rd party service fees, get the best rates, and receive personal service from our staff. Benefits of booking on this site or by calling us directly: Zero booking fees Lower resort fee More flexible cancellation policy Free early check in (based on availability!) Free room upgrades (when availa

Palm Tree Room - Pool, Hot Tub, Sauna, Spa

No kids, no pets. The Palm Tree Room is a spacious luxury bedroom in british colonial style with an ensuite bathroom. The bedroom has a king size bed and seating area with comfy chairs and a desk. Enjoy the large in-ground pool, 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 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.

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 - 103

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.

Classified Moto - The El Mayor 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 EL MAYOR ROOM has caught your eye. Let’s talk about it. Named for and inspired by El Mayor Tequila, this big cozy cave is deliciously refined and thoughtfully crafted.