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Boutique hotel vacation rentals near Chesapeake Bay

Find and book unique boutique hotels on Airbnb

Top-rated boutique hotel rentals near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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
4.82 out of 5 average rating, 219 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
A spacious sleeping area features a large bed adorned with a colorful quilt and accent pillows. Two elegant armchairs are positioned nearby, with a decorative fireplace and stained glass window providing character to the room. Soft lighting from a chandelier enhances the cozy atmosphere.
Hotel room in Havre de Grace
4.85 out of 5 average rating, 13 reviews

The Flagship of the Vandiver Mansion: Rodgers Room - Amazing fireplace, soaking tub, walk-in shower, porch...!

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.

Guest favorite
Hotel room in Rehoboth Beach
4.98 out of 5 average rating, 149 reviews

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!

Guest favorite
A charming three-story historic building with light yellow siding and a gray roof is framed by blooming trees. A large front porch with white railings and steps invites guests in. Several windows are adorned with white shutters, adding to the welcoming appearance.
Hotel room in Williamsburg
4.92 out of 5 average rating, 49 reviews

Armistead House - Room 302 (3rd Floor)

This listing is for The Edison 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
The grand exterior of the Laughing King Retreat is framed by lush greenery and a well-manicured lawn. The two-story building features a welcoming porch with rocking chairs, large windows, and gabled roofs, creating a classic and inviting ambiance.
Hotel room in Cape Charles
4.98 out of 5 average rating, 202 reviews

The Laughing King Retreat, Cedar 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 enjoys 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 captured from the front, showcasing its white exterior and multiple gabled roofs. Lush greenery and vibrant flower beds surround the entrance, while large windows provide a glimpse of the inviting interior. A sign indicates the restaurant and inn's welcoming presence.
Hotel room in Onancock
4.88 out of 5 average rating, 150 reviews

Maurice Inn and Fusion Bistrot Blue Room 2nd floor

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, 31 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
Hotel room in New Castle
4.95 out of 5 average rating, 218 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
An inviting bedroom with orange walls and a king bed featuring soft white linens. Two framed motorcycle prints adorn the wall above the bed, while nightstands with lamps sit on either side. A carpeted floor adds warmth to the space.
Hotel room in Richmond
5 out of 5 average rating, 42 reviews

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.

Top guest favorite
Hotel room in Oxford
4.97 out of 5 average rating, 164 reviews

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.

Guest favorite
A spacious bedroom is shown with a plush velvet headboard on a king-size bed, dressed in crisp white linens. Beside the bed, a gold nightstand holds a small lamp. A cozy seating area features two armchairs and a side table. A decorative fireplace adds to the room's charm.
Hotel room in Alexandria
4.94 out of 5 average rating, 114 reviews

★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.

Guest favorite
A cozy basement room features a full-sized brass bed dressed with soft linens. Exposed brick walls add unique character. A plush armchair and a wooden side table provide comfortable seating, while a tasteful area rug enhances the space.
Hotel room in Petersburgh
4.97 out of 5 average rating, 121 reviews

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

Quick stats about boutique hotel rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 60 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at G$16,719 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,910 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Chesapeake Bay vacation rentals include wi-fi 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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