
Bungalow rentals near Chesapeake Bay
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Top-rated bungalow rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

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!

🌅🎢Bungalow 1 block to boardwalk on 4th st!
Private yard 🌞 Outdoor shower 🚿 Premium cable/ NFL RedZone/ MLB ticket! 🎟️ Beach 🚲 s Beach chairs and 🏖️! Come enjoy our 1940s bungalow, just one block from the boardwalk, one block from the bay, and brand new downtown park. Our cozy retreat offers a unique blend of vintage appeal and modern amenities. Enjoy the provided beach chairs and umbrella, afternoons in the yard, rinse off under the outdoor shower after the beach, cook in our fully stocked kitchen, or explore town on a bike.

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.

Romantic Saltbox Bungalow! HOT TUB! Bay Sunsets!
Stylish, romantic & cozy getaway! 2.5 blocks to gorgeous sunsets on a secluded bay beach! Linens, towels & Turkish beach towels provided. This quaint & quirky house is the perfect place for an adult respite (only non-crawling infants & kids 5 yrs & up). Stocked w/ everything you need: hot tub, gas fireplace, beach supplies, bikes, bar cart, seasonal outdoor shower, 2 fire pits, picnic table, screened in porch w/dining table & lounge area! Fun, seasonal beach bar (Harpoons) walking distance!

Baybreeze Bungalow Luxury Couple’s Retreat
Baybreeze bungalow by the bay, is just blocks from the beautiful Cape May sunsets and the Cape May-Lewes Ferry. The entire bungalow is your home during your stay. It is a short walking distance to the beach and a close drive or bike-ride to the center of Cape May. This lux bungalow sleeps 2 comfortably and is great for adult getaways. All amenities for a great, worry-free, and relaxed stay are provided for you. We do not allow dogs/pets in the bungalow. There will be a $100 penalty.

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.

Charming Bungalow
4 bedroom bungalow near historic Cold Spring Village & Brewery and Cape May Winery. Lovingly restored home with architectural charm, updated bathrooms and large open kitchen and living/dining area. Located within 3 miles of Cape May beaches. Washer/dryer, sunporch, deck, den/office and plentiful onsite parking. Back of 1.3 acre property provides private access to Cold Spring Bike Path with an outdoor shower and firepit.

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".

Sunflower Bungalow
THE SUNFLOWER BUNGALOW 🌻is a delightful space to unwind and take it easy. Kick back, relax and enjoy the calm and salt air. Walk to the bay and take in spectacular sunsets. Short drive to Victorian Downtown Cape May and beaches. Fresh duvet covers, linens, towels, shampoos, shower gel, and essential paper products all supplied to give you more time for yourself.
Popular amenities for bungalow rentals near Chesapeake Bay
Beachfront bungalow rentals

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

Bayside | Walk to Sand • Fenced Yard • EV Charger

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.

Unique Beach Bungalow Pool Steps to Beach

Bayside Bungalow: Cozy North Beach Getaway
Private bungalow rentals

Walkable Carytown Charmer | 2BR/2BA by James River

The Seapointe House

Cozy shore bungalow

Nature's retreat @ the Bug-a-Boo. Beaches nearby

Little Moondoggies Digs Coastal Bungalow

Private bungalow with fire pit near Easton, Denton

Quantico 2BR Home ~Train Potomac River Graduations

Light, Bright and Comfortable! No cleaning fee!
Other bungalow holiday rentals

The Yellow House: by Waterfront & Town Center

Bethany Beach Retreat - 10 Minutes to Ocean

1 Block to Bay • Pet-Friendly • EV + Paddle Boards

*Midterm/Longterm* Buckroe Beach Bungalow EV chrg

Charming Bungalow in the heart of Carytown

New, Chic River Bungalow in Historic District

Cozy bungalow minutes from James River

New Bungalow with view of the South River!
Other great holiday rentals near Chesapeake Bay

Private romantic pet friendly waterfront cottage

Peaceful Haven: nature & charming town

Historic St.Mary's City at the Lazy Bear Cottage

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

The Laughing King Retreat Honeymoon Island Cottage

Waterfront Guesthouse II on the Rappahannock

Cass-N-Reel Luxury Houseboat

Water's Edge Cottage | Luxury Retreat
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 $77 SGD per night before taxes and fees

Verified guest reviews
Over 3,520 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
20 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
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- Bungalow rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Cape Charles Beachfront
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