
Boutique hotel holiday rentals near Chesapeake Bay
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Top-rated boutique hotel rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

The Tydings at the Vandiver: Victorian elegance, stunning fireplace and king bed.
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 Vandiver consists of the Historic Vandiver Mansion, the adjacent Kent & Murphy Houses, the year-round Pavilion and our Gardens. The Tydings (Premium / 2nd Floor Vandiver Mansion): Elegant 4-Poster King Bed. Calming Sage and White hues complement Tyding's French Poster Art and beautiful white brick mantle, and eco-Fireplace. Can be connected to Fair Room via a private hallway to create a huge 2-bedroom, 2-Bath Grand Suite. Standard Tub w/Shower. Special Stuff: ecoFireplace / Four-Poster King Bed / Beautiful Brick Mantel

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.

Sea Grass Room - Pool, Hot Tub, Sauna, Spa
No kids, no pets. The Sea Grass Room is a luxury bedroom decorated in coastal style with a queen-size bed, and ensuite bathroom. Includes mini-fridge, 4k UHD smart TV, Mar Bella robes and more. 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!

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.

“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.

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.

★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.

The Hearth Room - Strawberry Hill Petersburg
Walled by the original granite foundation dating to 1792, The Hearth Room is Strawberry Hill’s cozy and inviting basement room. Accessible by a private entrance on the west side of the building, this is the only pet-friendly room at Strawberry Hill. Featuring a full-sized brass bed, a 50” smart TV, and antique furnishings, your stay promises to be comfy and memorable.
Popular amenities for boutique hotel rentals near Chesapeake Bay
Family-friendly boutique hotels

Seagull Room - Pool, Hot Tub, Sauna, Spa

Scenic King Room | Garden Views & Easy Access

Upscale and Great Location

Room with Balcony/View

The Laughing King Retreat, Cobb Island Suite

Charming Boutique Haven on C&O Canal! Lock6

Maurice Inn and Fusion Bistrot Blue Room

Rehoboth Beach downtown dog friendly Canalside Inn
Boutique hotels with a patio

Luxury 1 Bedroom 1 Bath Kingsmill Resort

Barksdale Suite - Strawberry Hill, Petersburg

2BR + 2BA - Family friendly

Romantic Victorian Castle SuiteJ

Armistead House - Room 302 (3rd Floor)

The Charlesworth Hotel and Restaurant on the Bay

Armistead House - Room 201 (2nd Floor)

Armistead House - Room 301 (3rd Floor)
Other boutique hotel holiday rentals

GLEN ROCK MILL INN Suite #11-Queen Bed-Executive

The Laughing King Retreat, Cedar Island Suite

Starfish Room - Pool, Hot Tub, Sauna, Spa

Coral Reef Suite - 2 rooms, Pool, Hot Tub, Sauna,

The Laughing King Retreat, Rogue Island Suite

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

GLEN ROCK MILL INN Suite #10-King Bed

Maurice Inn and Fusion Bistrot Blue Room 2nd floor
Quick stats about boutique hotel rentals near Chesapeake Bay

Total holiday rentals
Explore 60 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $102 SGD per night before taxes and fees

Verified guest reviews
Over 2,910 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
40 of Chesapeake Bay holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

4.8 Average rating
Chesapeake Bay stays are highly rated by guests – averaging 4.8 out of 5!
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