
Loft holiday rentals near Chesapeake Bay
Find and book unique loft accommodation on Airbnb
Top-rated loft rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

New Loft w/South River view from treehouse deck!
Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern apartment that has a treehouse style deck for relaxing and enjoying the outside. The unit is served by a separate entrance and free street parking. Bring your kayak or stand-up-paddleboard, or try your luck at fishing! The TV is upgraded to a 55". Downtown Annapolis is just 6 miles away and offers cultural attractions, bars and restaurants, historical tours and access to the Naval Academy.

Modern 2BR Treetop Oasis on Historic Logan Circle
Guests describe our Airbnb as an ideal balance of modern living and historic charm. This extraordinary, light-filled, airy loft apartment is the top 2 floors of our private home, an iconic Logan Circle Victorian. It peers out onto the treetops of Logan Circle Park and neighboring historic homes. Totally private with its own entrance, the apartment is accessed by elevator. We are in the heart of the Nation's Capital, within easy walking, cycling, or transit distance to all the city has to offer.

The Riverfront Loft
Riverfront loft in the heart of Old Town, steps from Potomac River and King St! New construction studio apartment in a 19th century warehouse with a private roof deck, modern appliances, marble countertops, plush furniture, eat-in kitchen. Great for entertaining, biz travel (fiberoptic 100 MB/sec speed), a romantic getaway, or a week of sightseeing in the nation's capital and water taxi to DC, National Harbor/MGM. Sleeps two comfortably in king bed with option for two more on pull-out couch.

Romantic chalet Old Town Alexandria
Welcome to Old Town Alexandria! Just minutes from downtown DC and DCA airport! Right in between the subway and the river, this apartment is the entire top floor of a historic 1880’s building right on King St. It is a loft apartment with a full bath and kitchen w/ large living room space. Bedroom is separate but access to bathroom is through the bedroom. This is a romantic spot with west facing windows where you can sit at the bar with your glass of wine watching the sunset! Pets stay for free!

Designer owned Coastal getaway retreat
Enjoy our private, above-garage hideaway apartment with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance. Come and go as you please! Note: We are a peanut-free and smoke free property. RELAX in our chic, private loft just minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach just a 5 minute drive away. Please let us know if you plan to use it!

Tree Top Loft
Studio apartment is located on a wooded lot in a quiet neighborhood within 4 miles of Salisbury University & Downtown! Off street parking at entrance patio & a flight of stairs leads up to the apartment, which includes a queen size bed, full kitchen with full size refrigerator, 4 burner electric stove, full size washer and dryer. Bathroom includes shower, toilet and vanity, perfect for a week or weekend stay! We are located near Ocean City, Maryland, Assateague National Seashore.

Cozy Barn Loft: Country Views & Central to Beaches
Relax and recharge as you soak in the country views while enjoying this cozy space. A private entrance leads upstairs to the loft, located above our renovated barn. Enjoy your days at the beach, boating, fishing, birding, and more. Return home to be greeted by goats as you pull in the drive. Coffee, tea, and farm fresh eggs will be waiting for your arrival. Centrally located between the beaches of Chincoteague, Va and Ocean City, MD. Beach gear provided as well.

Historic Bank Loft | King Bed | Luxury Spa Shower
Stay in a unique apartment inside the former historic Polish Bank, where a grand marble-columned façade welcomes you into a beautifully restored space blending timeless architecture with mid-century modern design. This 800-square-foot second-floor apartment features original vaulted ceilings, dramatic column-lined walls, and preserved details from the 1800s. Styled with modern furnishings, it offers a refined luxury stay full of character, history, and comfort.

Retro Hipster: Close to downtown, dining and fun
Want to stay in a place with a Jazzy retro style? This is the perfect place for you. This renovated 2 bedroom, 2 bath apartment features beautiful riverfront views, high ceilings, wifi, smart TV’s and a bit of History. This is part of a hotel from the Green Book era where Etta James and Billie Holiday both stayed. This space is perfect for business travelers, couples and families looking for place near in downtown Salisbury or a short drive from the beach.

Serene Flat at U/14th St in Shaw on Quaint Swann
Luxurious, private and comfortable retreat in the heart of the most bustling part of DC in the U Street/14 Street corridor. Steps to the best of city living, while on one of the most beautiful, quiet streets in DC, enjoy this award winning, sunny 1 BR penthouse flat. As architects, we've designed beautiful spaces in DC, so expect gorgeous finishes and thoughtful touches throughout. Beautiful modern renovation to historic brick walled home.

Waterfront Barn Loft with Modern Cabin Vibe
Relax in nature for a while in our beautiful and cozy barn loft. The loft is located next to our primary residence on 7 private acres along scenic Rewastico Creek, offering year round beauty. Kayak on, or relax by, the tidal marsh creek which is fed by the Nanticoke River and Chesapeake Bay. Centrally located between popular Eastern Shore destinations such as Atlantic beaches and historic small towns. A serene oasis with abundant wildlife.

Beautiful newly updated apartment in Fairton.
Forget your worries in this spacious and serene space. This recently renovated second floor apartment boasts natural light and nature at your footsteps. It has every comfort needed to feel like you're right at home. It is conveniently located close to New Jersey Motor Sports Park and the Delaware Bay. It has plenty of space to park large trailers and boats. NO SMOKING PET FRIENDLY (pets must be clean)
Popular amenities for loft rentals near Chesapeake Bay
Family-Friendly loft accommodation

Bull Island Getaway - Cozy Suite Near Yorktown

UpperLVL/Loft/Farmhouse sleeps 8/WineCountry

Lovely one bedroom loft close to the beach

Country Loft. Private, comfy, special.

Quiet Empty Nest - North Wilmington

The Loft at East Patrick

Cozy Pine Tree Nest

Perfect for visiting Washington DC!
Loft rentals with a washing machine and dryer

Stylish Historic Apartment - Queen Bed, Fast WiFi,

Beautiful 1-bedroom Loft in Fan District

STUDIO SUITE IN THE TREE TOPS:ADAMS MORGAN,WOODLEY

Cozy City Loft walk to JHH & Fells

Loft at Fountain Park - Prime Downtown Location

Cute and private loft apartment

Cute loft;Heart-of-City;120in Movie Screen;Parking

Snapper Rocks - Loft #8 - 8 min walk to the beach
Other loft holiday rentals

Secluded Annex in Historic Church Hill

Solar Powered Studio Suite

102 in Cockade City Flats Licensed

Downtown Richmond/2 Bed Loft

Louise Hand Laundry | Logan Circle | Rare & Iconic

Steps from Downtown Restaurants 2BR Vibrant Apt

The Pond Apartment

Carriage House loft by lake with wood-fired sauna
Quick stats about loft rentals near Chesapeake Bay

Total holiday rentals
Explore 30 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $101 AUD per night before taxes and fees

Verified guest reviews
Over 2,790 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Chesapeake Bay holiday rentals include Wi-Fi access

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

4.9 Average rating
Chesapeake Bay stays are highly rated by guests—averaging 4.9 out of 5!
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