
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.

Bowers Beach: A Slice of Paradise
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.

Beachside Cottage: Yard, Porch, Walk to BEACH
Step into this bright 1940s beach cottage, just a short walk from Chesapeake Bay and local dining spots. Bedroom 1: Queen bed Bedroom 2: Two twin beds with a trundle, convertible to a king Relax on the breezy front porch or under the live oak in the serene backyard. Enjoy an equipped kitchen, cozy dining area, comfortable living room, and in-unit laundry for your convenience. Ideal for families, couples, or medium-term stays, this charming retreat promises comfort and proximity to the beach.

Walkable Carytown Charmer | 2BR/2BA by James River
Experience Richmond like a local in this cozy, renovated home located in one of the city’s most beloved neighborhoods. This 2-bed, 2-bath entire home blends charm, comfort, and walkability—perfect for couples, small families, wedding guests, or a relaxed getaway with friends. Step outside and your moments from everything that makes Richmond special. Walk to the shops, restaurants of Carytown, explore cultural landmarks, etc. Outdoor lovers will appreciate being just minutes from River access!

Charming Bungalow in the heart of Carytown
Perfect Richmond Bungalow located in the heart of Carytown. House includes: internet, full kitchen, dining room, office space, front porch, and a fenced-in front and back yard. In walking distance from restaurants, shopping, a brewery, and grocery stores. Located near Byrd Park, the Carillon, and Maymont park and is less than a mile from the VMFA and Virginia Museum of History. Dog friendly - no other animals permitted *New backyard fence, new pullout sofa-bed, and freshly painted interior*

🌅🎢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.

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.

Renovated Carytown Cottage w/ Parking & Fire-pit
This lovely renovated cottages all of the essentials and includes a fully stocked kitchen with complimentary coffee. Two bedrooms each with cozy queen beds are perfect for your couples getaway or a romantic weekend. A small but stylish Jack and Jill bathroom connects the 2 rooms. Enjoy the mornings on the front porch or evenings on the screened porch after walking to dinner on Cary Street! Shopping, brunch, cocktails..it's all right here. One off street parking spot available offsite.

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.

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!

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

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

SUN HOUSE: Artist's bugalow on a sanctuary dune

Bayside Bungalow: Cozy North Beach Getaway

Bayside | Walk to Sand • Fenced Yard • EV Charger

The Real Thing-BEACH HOUSE! 2 bd 2 bath!

New! Sandy Dunes on the Bay
Private bungalow rentals

The Yellow House: by Waterfront & Town Center

Mid century Ranch minutes to beach and base

Charming 3BDR Bungalow Near Annapolis

Cozy shore bungalow

New, Chic River Bungalow in Historic District

Casa Pinturella

Private Suite in 1917 Craftsman 15 min to Harbor

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

The Purple Pad - Ocean City MD beach block cottage

Behind the Red Door in Rehoboth Beach

Welcome to Mermaid Haven!

*Midterm/Longterm* Buckroe Beach Bungalow EV chrg

56th Street Beach Boys Bungalow

Pet-Friendly Downtown Beach Bungalow

Key West Bungalow by the Bay

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

Relaxing Water Views - Mill Creek Cottage

The Laughing King Retreat Honeymoon Island Cottage

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Long Beach Cottage, Hot Tub, Beachfront

Hideaway on the Bay: Waterfront Vintage A Frame

Waterfront-View of Bay from your Bed

Kent Island Waterfront Home with Amazing Sunsets

Beach Front and 'Perfectly Placed'
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 3,430 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 20 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!
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- Bungalow rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
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- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
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