Boutique hotel vacation rentals near Chesapeake Bay

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Top-rated boutique hotel rentals near Chesapeake Bay

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Superhost
A well-appointed bedroom features a spacious bed with a blue accent pillow. Light blue wall designs create a soothing atmosphere, while a large mirror reflects the bed. Nightstands with lamps are positioned on either side, adding functionality to the inviting space.
Hotel room in Fredericksburg
4.83 out of 5 average rating, 178 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.

Superhost
Hotel room in Glen Rock
4.92 out of 5 average rating, 128 reviews

GLEN ROCK MILL INN Suite #2- Interior-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.

Superhost
A spacious bedroom features a luxury king-size mattress covered with crisp white bedding. Lighting is provided by two bedside lamps, and a flat-screen TV is mounted on the wall. Large windows overlook a grassy area, allowing natural light to fill the room.
Hotel room in Williamsburg
5 out of 5 average rating, 3 reviews

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.

Guest favorite
An aerial view captures a vibrant blue hotel surrounded by lush greenery. A large in-ground pool is centered among patio furniture and shaded areas. Several guests can be seen enjoying the pool, which is framed by lounge chairs and umbrellas, enhancing the outdoor relaxation space.
Hotel room in Rehoboth Beach
4.98 out of 5 average rating, 131 reviews

Palm Tree Room - Pool, Hot Tub, Sauna

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!

Top guest favorite
A watercolor painting depicts a serene waterfront scene with boats on the water. A historic yellow building is visible, surrounded by trees and additional structures. The tranquil atmosphere is enhanced by the clear skies and gentle ripples reflecting light on the surface.
Hotel room in Oxford
4.97 out of 5 average rating, 150 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 favorite
The historic Armistead House is presented in a charming yellow exterior, framed by trees with blooming foliage. A spacious front porch features white railings, while multiple windows adorn the façade, allowing natural light to fill the interior. A paved path leads to the entrance.
Hotel room in Williamsburg
5 out of 5 average rating, 81 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.

Guest favorite
Hotel room in New Castle
4.89 out of 5 average rating, 115 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 favorite
A classic multi-story retreat is framed by lush greenery and neatly landscaped grounds. The spacious front porch, furnished with rocking chairs, welcomes guests. A circular garden bed, adorned with colorful flowers, enhances the inviting exterior under a clear blue sky.
Hotel room in Cape Charles
4.97 out of 5 average rating, 199 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 favorite
A charming boutique inn is depicted, featuring a classic white exterior with dark shutters and a welcoming sign. Lush gardens with colorful flowers border the property, while large windows allow natural light into the building. The inviting front porch is visible, enhancing the overall aesthetic.
Hotel room in Onancock
4.85 out of 5 average rating, 143 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 favorite
The exterior of a two-story building features a modern design with white siding and dark trim. Large windows and a welcoming front porch are visible, complemented by manicured landscaping. A green sign near the entrance lists the property name, indicating a charming ambiance.
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.

Top guest favorite
The entrance to The Terry House is framed by a sturdy black door adorned with intricate carvings. A welcoming sign hangs beside the door, and the steps are flanked by neatly trimmed shrubs in black planters, adding an inviting touch to the historic brick façade.
Hotel room in New Castle
4.95 out of 5 average rating, 169 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.

Top guest favorite
A spacious bedroom features a dark brick fireplace with an ornate mirror above it. Two comfortable chairs are positioned near the windows, which are dressed with light curtains. A plush area rug adds warmth to the hardwood floor, while a minimal bed awaits use.
Hotel room in Norfolk
4.98 out of 5 average rating, 123 reviews

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 vegetarian natural wine bar and 2-bedroom inn. 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!

Popular amenities for boutique hotel rentals near Chesapeake Bay

Quick stats about boutique hotel rentals near Chesapeake Bay

  • Total rentals

    80 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    2.8K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    10 properties have a pool

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