Some info has been automatically translated. Show original language

Boutique hotel holiday 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.

%{current} / %{total}1 / 1
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, 211 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
A bride twirls gracefully in a flowing white dress, with soft fabric cascading around her. The elegant room features a dark brown leather couch and vintage decor, illuminated by a crystal chandelier. Light streams through large windows, enhancing the warm color palette of the space.
Hotel room in Havre de Grace
5 out of 5 average rating, 9 reviews

The Stockett 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.

Top guest favourite
Hotel room in Glen Rock
4.95 out of 5 average rating, 132 reviews

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.

Guest favourite
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, 48 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 favourite
An aerial view captures a vibrant blue pool surrounded by lounge chairs and umbrellas. Several guests enjoy the water, with expansive outdoor seating areas visible on the patio. A sunny environment enhances the inviting atmosphere of the property, framed by lush greenery.
Hotel room in Rehoboth Beach
4.92 out of 5 average rating, 152 reviews

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!

Guest favourite
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, 200 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
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
4.86 out of 5 average rating, 149 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
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 favourite
Hotel room in New Castle
4.95 out of 5 average rating, 204 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 favourite
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, 33 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 favourite
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, 160 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.

Superhost
A charming entrance features a set of stone steps leading to double doors framed by lush greenery and seasonal blooms. Outdoor seating is arranged on either side, complemented by trees providing shade. Brickwork adds a historic touch to the elegant facade.
Hotel room in Washington
4.79 out of 5 average rating, 523 reviews

Historic DuPont Circle Inn ~ Canopy Room

Indulge yourself in the rich history of one of DC's most historic and cherished Inn's The DuPont Circle Inn. An elegantly furnished Victorian Brownstone situated on DuPont's most ideal corner Q Street, steps to the metro,the famous Kramer books and the world class living Washington has come to love. Each room comes fully appointed with a Queen tempurpedic bed, microwave and kettle, desk and soft luxurious linens.

Popular amenities for boutique hotel rentals near Chesapeake Bay

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 £59 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!

Destinations to explore