Boutique hotel vacation rentals near Chesapeake Bay

The Fair 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.

GLEN ROCK MILL INN Suite #1-King Bed

CONTINENTAL BREAKFAST INCLUDED. Each of the rooms in the historic mill, turned full service restaurant & hotel, offers old world feel, with clean modern amenities. 200 year old brick, hand-hewn beams and uneven plank floors blend with well dressed beds, tile showers, pedestal sinks and new fixtures. Dine with us, explore nearby gift & antique shops, enjoy historic tours and wineries all within a 30 minute radius. Located directly on the York County Heritage Rail Trail, we are bicycle friendly.

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.

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.

Blue Heron Room - Pool, Hot Tub, Sauna, Spa

No kids, no pets. The Blue Heron Room is a spacious luxury bedroom with a vaulted ceiling, king-size bed, private ensuite bathroom and private garden patio. Enjoy the large in-ground pool, the huge jetted spa/hot tub and Himalayan salt sauna, hammocks, fire pits and more. 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!

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 on C&O Canal ~ Workspace! Lock9

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.

The Hotel at Classified Moto - Schnickschnack Room

We’re stoked you’ve discovered The El Mayor Room at Classified Moto! Our new custom designed hotel near downtown Richmond has five artfully crafted guest rooms to choose from and an array of great common areas to relax and work. If you love a good vibe and want something beyond the typical chain hotel experience, you’re in luck. Some like bright and breezy — some prefer moody and vibe-y. If you’re the latter, The Schnickschnack Room is your huckleberry.

Sandaway Suites & Beach Boutique Hotel, Water View

Sandaway Suites & Beach is located in historic Oxford, MD, within walking distance of local shops and dining. Our boutique hotel offers stunning waterfront views and a private sandy beach on the Eastern Shore. Stay in one of our beautifully restored water-view rooms, blending in-room comforts with in-town convenience. Take a day trip to St. Michaels, Easton, or Cambridge, then return to Sandaway’s private beach to experience an unforgettable sunset.

Beach Bum Inn Beach Bum Inn 3rd Cityview 2 D

Benefits of booking on this site or by calling us directly: Zero booking fees Lower resort fee More flexible cancellation policy Special promotions available Free early check in (based on availability!) Free room upgrades (when available) We will price match, Street view room with 2 double beds and private balcony. Offering compact parking for 1 vehicle, small indoor pool and grab-n-go breakfast. No smoking and sorry no pets.