
Loft vacation rentals near Chesapeake Bay
Find and book unique loft rentals 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.

Free Parking, Dogs • Walk to Breweries & Coffee
This charming downtown Frederick flat is made for foodies, coffee lovers, and city explorers. Just steps from Frederick’s top breweries and cafés, it’s the perfect home base for a weekend getaway with your pup. With pet amenities, local recs, parking, and fast Wi-Fi, it’s both fun and functional. Free parking in a dedicated spot on a gravel lot behind the home, which is a 2 minute walk to the front door. (Quick note: dogs must stay with their owners and be comfortable without excessive barking)

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!

The Cheriton Loft
Located in the heart of Cheriton, The Loft is a bright and sunny apartment. It is perfect for a couple and one child, three friends or one person. Cheriton is an up and coming village which is home to several galleries and an art center. It is less than 4 miles to the charming town and beach of Cape Charles, 3 miles to Oyster Boat Landing and 8 miles to Kiptopeke State Park. The apartment is owned and decorated by"The Sheep Lady", a local painter, illustrator and writer of children's books.

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.

Cozy City Loft walk to JHH & Fells (pets welcome)
Comfortable loft with tons of natural light. Walking distance to light rail station, Johns Hopkins Hospital and the historic port community of Fells Point with cool dive bars and great restaurants. The apartment is very peaceful and surprisingly serene for a busy city street. We do not allow smoking at all on the property. Grab an uber for a short ride to fine dining at Harbor East or get dropped off at a divey port bar for pints and live irish music

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.

Chic Loft | Rest and Relax l Private Beach Access
Outage worker welcome: 1 guest. orefer night sleeper as we will come and go thru garage during the day and the dog will bark..We cant guarantee quiet daytime sleeping conditions Relax in a chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. Enjoy our private, above-garage hideaway with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home.

Serenity
Enjoy the natural serenity of this spacious waterfront hideaway on the historic Antipoison Creek (so named by Capt John Smith), minutes to the Chesapeake Bay by boat or car. The area offers boating, fishing, a nature trail and an abundance of wildlife (deer, turkeys, waterfowl, bald eagles, osprey. otters and more) on this 7 acre property. Water views, king bed, sofa and full kitchen with dinette.
Popular amenities for loft rentals near Chesapeake Bay
Family-friendly loft rentals

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First Floor Studio near Jolly Roger and the Beach!
Quick stats about loft rentals near Chesapeake Bay

Total vacation rentals
Explore 20 vacation rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Chesapeake Bay vacation 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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- Loft rentals United States
- Virginia Beach Oceanfront
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- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Cape Charles Beachfront
- Norfolk Botanical Garden
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- Chrysler Museum of Art
- The NorVa
- Nauticus
- Colonial Williamsburg's Merchants Square
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- Chrysler Hall
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