
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.

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.

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 Metro distance to all the city has to offer.

The AlleyLight - Havana Oasis
Welcome to The AlleyLight BnB! A Havana Nights inspired stay. This home is built to teleport you into your own personal world. A romantic setting with warm lighting or a professional getaway with designated work areas. Nestled right into downtown Richmond (the FAN), minutes away from VCU, UR, the business district and Cary Town! Food, Drinks, and fun are just a walk away when you're staying with us. Please note: this is a historic home, the stairs and bathrooms are smaller than modern homes.

Chic Loft | Rest and Relax Near Solomon's & Beach
STAY IN or ADVENTURE OUT 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. Our open-concept space, has a bedroom area, bathroom, workspace, living room & kitchen. SMOKE FREE SCENT FREE PET FREE PEANUT FREE We offer an Air Purifier and use only all natural cleaning products.

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.

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.

Charming Loft Apt. Old Town Alexandria
Charming and rustic little apartment overlooking a beautiful restaurant garden in the heart of old town with its own balcony. Come stay in our quaint and cozy little loft apartment while visiting historic Alexandria! This is a unique place in an old building and you will never find anything like this in a hotel! The second bed is in the loft up a steep ladder, so not suitable for small children or those with mobility issues.

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.

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 rentals

Bull Island Getaway!

In the heart of Scott's Addition!

Country Loft. Private, comfy, special.

Cozy Pine Tree Nest

102 in Cockade City Flats Licensed

Modern Loft with Skyline Views - King & Queen Beds

Perfect for visiting Washington DC!

The Pond Apartment
Loft rentals with a washer and dryer

Nicely Appointed 1 Bedroom Loft Apartment

Beautiful 1-bedroom Loft in Fan District

Louise Hand Laundry | Logan Circle | Rare & Iconic

Cozy City Loft walk to JHH & Fells (pets welcome)

Loft at Fountain Park - Prime Downtown Location

Cute and private loft apartment

Luxury Downtown Loft

The Riverfront Loft
Other loft vacation rentals

Secluded Annex in Historic Church Hill

Lovely one bedroom loft close to the beach

Loft w Private Entrance, Kitchen, Prime Location

Downtown Richmond/2 Bed Loft

Deluxe corner apartment with riverfront views

The Loft in Willow Lawn

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

Trestles - Loft #5 - 8 min walk to 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 G$10,458 GYD per night before taxes and fees

Verified guest reviews
Over 3,150 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!
Destinations to explore
- Bed and breakfasts Chesapeake Bay
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- Loft rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Assateague Beach
- Haven Beach
- Buckroe Beach and Park
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Piney Point Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
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- Wilkins Beach
- James River Country Club
- Little Creek Beach
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