
Bungalow rentals near Chesapeake Bay
Find and book unique bungalows on Airbnb
Top-rated bungalow rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Quantico 2BR Home ~Train Potomac River Graduations
This 1925 Bungalow is a relaxing space whether visiting Quantico for TBS/OCS/FBI graduations or sightseeing. Amtrak and VRE train stop under 5 minute walk direct to Alexandria, Crystal City, or DC (Union Station). In town you can fish, watch the sunset at the Potomac River, visit restaurants, or drive 5 minutes to the golf course (open to public). For DoD Cardholders it is 7 min walk to theater/gym/bowling. Town access is through military base. REALID is needed to use the highway to town

A Slice of Paradise: Bowers Beach
Please note: We require guests to book the total amount of persons staying as we charge per-guest. We do not have a TV and our home is not suitable for unsupervised young children. Between Whitwell’s Delight and Bowers Beach Road, across from the old Tuthill Brothers Farm, we have a quiet space that is perfect for up to eight people to feel at home; great for couples or a tight-knit group of friends or family. We also have records, board games and puzzles to enhance the feeling of a cozy stay.

Cozy Retreat Bungalow 20 min to downtown Baltimore
Welcome home! Whether you are in town for business or leisure, this home will meet your needs at a very competitive price, and we are only 20 minutes from downtown Baltimore. If you're looking for a clean, comfortable, airy, and memorable home for your trip, congratulations, you just found it! No more worries about finding parking, handling the noise from neighbors above or below you, or sharing the house with anybody else. The entire house is all yours to enjoy. You will enjoy your stay here!

Nature's retreat @ the Bug-a-Boo. Beaches nearby
We're inside a lovely gated campground community with full amenities @ the Club House: Wi-Fi, pool, fishing n crabbing, boat ramp, laundry, and bath houses. The Bug-a-Boo is a lovely single dwelling home. It is ADA handicap accessible. There's an outdoor fire pit and space for camping. We are 20 miles from Chincoteague National Wildlife Refuge with miles of protected beaches. This is a peaceful place for soul searching & social distancing. We are also 42 mi from Assateague Is. Nat. Seashore.

Private Suite in 1917 Craftsman 15 min to Harbor
- 5 miles from Inner Harbor, Orioles and Ravens Stadiums, Johns Hopkins Hospital, Fells Point - Free off-street parking in charming safe well-lit neighborhood - Fastest WiFi and Laptop friendly - Pets must be preapproved. Do not book without contacting host - “5-star experience, just like home” Totally private suite including bedroom, bathroom, kitchenette and den, in a quiet, safe neighborhood in B’more’s quaint upper East side. Feel right at home in this friendly and inclusive space

Peaceful Setting with Chic, Thoughtful Style
Settle down for a peaceful night's sleep in the four-poster bed at this tranquil cottage in the woods. The soft gray color palette along with beautiful hardwood floors creates a calm, fresh feel, while the screen porch offers a quiet spot for restful afternoons. This serene retreat sits minutes away from Annapolis. The waterfront community has a beach a short walk away for launching kayaks and taking relaxing strolls. There is also easy access to Baltimore, Washington, and the Eastern Shore.

* Stunning Bungalow Perfect for Everyone *
You'll love your stay at this charming and cozy 1 level bungalow!! It offers a brand new high quality renovation convenient to all the Baltimore hot spots. The open layout coupled with stylish finishes and decor will make you feel right at home. It's fully stocked with almost every possible thing you could imagine for your use! Really no need to bring anything but yourself and clothes. The 3 bedrooms with a movable foldaway queen sofabed can sleep 8 comfortably. Plenty of parking available.

Reel Lucky on Lossing - Walk to Beach/Pet Friendly
3 bed/2 bath bungalow centrally located on "the Point" and walking distance to the beach and downtown Colonial Beach! Relax on the screened-in front porch. Perfect for both family and friends' gatherings, with two TVs and a kitchen ready for cooking. There is an outdoor shower and a shed with beach chairs etc. Monthly/weekly rentals available and there are restaurants, breweries, wineries, and a tiki bar nearby. It is close to Dahlgren and around 2 hours from DC. 10% military discount.

Hilltop @ Shiloh
Hilltop sits on a park-like estate. This NEWLY REMODLED Bungalow is part of a charming duplex, offering a private entrance and exclusive outdoor seating. Enjoy stunning views of rolling hills, ponds, and lush landscaping. Stay and refresh your soul in our peaceful cottage or explore! Close to breweries, wineries, the C&O Canal for biking and hiking, and antique shopping at the popular Lucketts Store. Just 11 miles to historic Leesburg, VA, Morven Park, or 15 miles to Frederick, MD.

Boatyard Bungalow, 6 beds; 2 Full Baths-Waterfront
The original schoolhouse for Edgemere that was built in 1898 and converted to a residential home/marina in the 1950s. With over 2,200 sq. ft., it's a perfect environment for wedding venue preparations, family and friend reunions. Please don't exceed maximum number of twelve (12) guests at any one time in the house, during the day; or ten (10) staying the night in the house. Additional Pirate & Mermaid Bath House on property will be available by end of May 2024.

North Bank Bungalow! Hot Tub, Near FAN & Maymont
Located two blocks from Maymont Park, a few blocks from Texas Beach, a mile to Cary Street and easy access to the rest of the fan! Includes internet, washer/dryer, coffee, office workspace, hot tub and fire-pit. Would be great as a corporate rental or for any occasion in RVA. Enjoy world renowned breweries including the new Veil Brewing location, top notch eats, arts and so much more all in close proximity!

The Bungalow... an Urban Oasis!
"The Bungalow" will delight the traveler looking for an urban oasis. Eclectic with 1942 charm. Covered porch is everyones favorite and overlooks relaxed garden and pond with privacy fencing. Downtown, Carytown, VFMA, Lewis Ginter Botanical Garden, Ballpark, VCU, multiple Breweries and unlimited culinary experiences are minutes away! (Look under "Other details to note" for Dog info".
Popular amenities for bungalow rentals near Chesapeake Bay
Beachfront bungalow rentals

The Barefoot Bungalow-Unit B-Steps From The Sand!

A Block to Beach | 5 Beds, King Suite, Walkable

The Barefoot Bungalow-Unit A-Steps From The Sand!

New! Sandy Dunes on the Bay

#Buckroe Bungalow ~Escape to the Beach 2mins Away!

SUN HOUSE: Artist's bugalow on a sanctuary dune

Waterfront Weekend Get Away.

Bayside Bungalow: Cozy North Beach Getaway
Private bungalow rentals

The Yellow House: by Waterfront & Town Center

Charming Bungalow in the heart of Carytown

*Midterm/Longterm* Buckroe Beach Bungalow EV chrg

New, Chic River Bungalow in Historic District

Cozy shore bungalow

New Bungalow with view of the South River!

City Tiny House | Femme Muse | Getaway | King |

Bright Bungalow - Kid and Pet friendly with a Yard
Other bungalow holiday rentals

*Top Floor Bungalow* | Downtown Hampton | 1 BR

Behind the Red Door in Rehoboth Beach

Your Home for the Holidays near Base and Beach

56th Street Beach Boys Bungalow

The Milton Bungalow - Midcentury Style Experience

Key West Bungalow by the Bay

Bungalow Sleeps 5, near the Choptank River

Beachside Cottage: Yard, Porch, Walk to BEACH
Other great holiday rentals near Chesapeake Bay

Private romantic pet friendly waterfront cottage

Peaceful Haven: nature & charming town

“Cabana by the Bay”-tiny home on a pier!

Waterfront Guesthouse II on the Rappahannock

Hideaway on the Bay: Waterfront Vintage A Frame

Waterfront-View of Bay from your Bed-Steamy Sauna

Waterfront Cottage Getaway Views/Kayaks/Fire Pit

Coastal Waterfront 1 Bedroom Cottage
Quick stats about bungalow rentals near Chesapeake Bay

Total holiday rentals
Explore 40 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at € 60 per night before taxes and fees

Verified guest reviews
Over 3,340 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 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
- Flat rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Rentals with a cinema Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- Holiday home rentals Chesapeake Bay
- Beach apartment rentals Chesapeake Bay
- Guest house rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- House rentals Chesapeake Bay
- Motorhome rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Bungalow rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Assateague Beach
- Haven Beach
- Buckroe Beach
- 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
- Cape Charles Beachfront
- Wilkins Beach
- James River Country Club
- Little Creek Beach
- Wallops Beach
- Sarah Constant Beach Park




