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.

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Superhost
A charming two-story house is shown, featuring a brick chimney and a small red door. The exterior is adorned with light-colored siding and surrounded by lush greenery. A wooden deck invites guests at the entrance, providing a welcoming touch to the quiet setting.
Bungalow in Frederica
4.74 out of 5 average rating, 188 reviews

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.

Guest favourite
The exterior of the home is framed by a colorful landscape of blooming azaleas in vibrant reds and pinks. A driveway leads up to the house, which is nestled among green trees, providing a serene and inviting ambiance.
Bungalow in Baltimore
4.98 out of 5 average rating, 283 reviews

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!

Superhost
The image captures the exterior of a charming blue house surrounded by vibrant flower beds, primarily featuring red blooms. A yellow sign displaying the house name and address stands prominently in the foreground. Soft evening light enhances the welcoming atmosphere.
Bungalow in Horntown
4.8 out of 5 average rating, 158 reviews

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.

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Bungalow in Norfolk
4.81 out of 5 average rating, 130 reviews

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.

Guest favourite
The welcoming front porch features a blue front door with a circular wreath. Colorful cushions are placed on the seating area, surrounded by potted plants. A sign promoting inclusivity is visibly displayed, contributing to a friendly atmosphere.
Bungalow in Richmond
4.82 out of 5 average rating, 106 reviews

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*

Top guest favourite
Bungalow in Ocean City
4.87 out of 5 average rating, 141 reviews

🌅🎢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.

Top guest favourite
The living room features a modern gray sectional sofa adorned with colorful cushions. A wooden coffee table rests on a large area rug, accompanied by two yellow accent chairs. Natural light enters through large windows, brightening the space and highlighting decorative wall art.
Bungalow in Edgewater
4.98 out of 5 average rating, 195 reviews

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.

Top guest favourite
A light-filled seating area features a cozy armchair and ottoman, complemented by two decorative side tables with lamps. A circular mirror hangs above a dark wooden dresser, and a textured rug rests on the floor, enhancing the inviting space.
Bungalow in North Cape May
4.98 out of 5 average rating, 338 reviews

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.

Guest favourite
The living area features a spacious layout with large windows allowing natural light to fill the room. Two patterned armchairs are positioned around a central console with a television. A light fixture hangs from the ceiling, complementing the hardwood flooring and neutral wall colors.
Bungalow in Sparrows Point
4.94 out of 5 average rating, 156 reviews

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.

Top guest favourite
The exterior of a quaint house features a black and white design with a front porch adorned by a vibrant American flag. The gravel pathway leads to the entrance, surrounded by small potted plants and a spacious, tree-lined yard.
Bungalow in North Cape May
4.99 out of 5 average rating, 351 reviews

Romance at Saltbox Bungalow! HOT TUB! Bay Sunsets!

Stylish, romantic & cozy beach house just 2.5 blocks from incredible Delaware Bay sunsets. Perfect for couples or close friends seeking a peaceful escape near Cape May. This quaint & quirky retreat is stocked with everything you need: hot tub, gas fireplace, bikes, beach gear, bar cart, 2 fire pits, seasonal outdoor shower, screened porch w/ dining & lounge space. Linens, towels & Turkish beach towels included. Walk to the fun seasonal bayside bar Harpoons!

Guest favourite
Bungalow in Richmond
4.91 out of 5 average rating, 296 reviews

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!

Top guest favourite
The bungalow features a covered porch adorned with string lights, accented by a manicured garden and flowering plants. The brick exterior is complemented by a welcoming entryway, creating an inviting atmosphere. Meticulous attention to cleanliness is emphasized in the home’s maintenance.
Bungalow in Richmond
4.98 out of 5 average rating, 691 reviews

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

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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