Boutique hotel holiday rentals near Chesapeake Bay

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Top-rated boutique hotel rentals near Chesapeake Bay

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Superhost

Hotel room in Fredericksburg

4.82 out of 5 average rating, 164 reviews

Deluxe King Suite in Boutique Hotel

SCH is Fredericksburg’s newest luxury boutique hotel offering the comfort of a First Class hotel with the ease of a fully automated check-in experience. Perfect for those guests needing an Extended Stay in the Fredericksburg area as every guest suite is a welcoming residential style retreat featuring a spacious living room - a separate well appointed bedroom - full kitchen equipped with Whirlpool appliances including a full size refrigerator - range - dishwasher - microwave - as well as a washer and dryer. At SCH our guests have exclusive access to our 16000 square foot Clubhouse offering complimentary daily continental breakfast and shared coworking spaces equipped with all the essentials you will need for on-the-road productivity. Our Clubhouse access includes state-of-the-art fitness center - resort style pool - game room - spa area with steam and sauna as well as a massage room. Amenity offerings can change due to the COVID19- pandemic.

Guest favourite

Hotel room in Glen Rock

4.87 out of 5 average rating, 159 reviews

GLEN ROCK MILL INN Suite #10-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.

Top guest favourite

Hotel room in Oxford

4.96 out of 5 average rating, 131 reviews

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.

Top guest favourite

Hotel room in Williamsburg

5 out of 5 average rating, 73 reviews

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.

Superhost

Hotel room in Petersburgh

5 out of 5 average rating, 10 reviews

Barksdale Suite - Strawberry Hill Petersburg

Stay a short walk away from Petersburg's urban amenities in Strawberry Hill, a one-of-a-kind, lovingly restored home built in 1792. Once you arrive you will feel like you stepped into the 18th century. Named for Strawberry Hill’s first owner and inhabitant, the Barksdale suite impresses in black and gold splendor. Complete with a king bed, attached sitting room, and private bathroom, this room is Strawberry Hill’s most accessible room, just steps from the front door on the first floor.

Guest favourite

Hotel room in New Castle

4.86 out of 5 average rating, 96 reviews

“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.

Top guest favourite

Hotel room in Rehoboth Beach

4.98 out of 5 average rating, 102 reviews

Blue Heron Room - Pool, Hot Tub, Sauna

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!

Top guest favourite

Hotel room in Cape Charles

4.97 out of 5 average rating, 192 reviews

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.

Guest favourite

Hotel room in Onancock

4.85 out of 5 average rating, 131 reviews

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 favourite

Hotel room in North Beach

4.97 out of 5 average rating, 30 reviews

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.

Guest favourite

Hotel room in New Castle

4.94 out of 5 average rating, 145 reviews

“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.

Guest favourite

Hotel room in Norfolk

4.97 out of 5 average rating, 119 reviews

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!