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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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, 276 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!

Guest favourite
Bungalow in Ocean City
4.87 out of 5 average rating, 137 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
A serene bedroom features soft blue walls and a cozy bed adorned with floral bedding. Two armchairs with decorative pillows are positioned beside the bed. Light streams through sheer curtains, illuminating framed artwork of hot air balloons on the walls.
Bungalow in Baltimore
4.99 out of 5 average rating, 102 reviews

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

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, 194 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.

Guest favourite
A spacious living area is furnished with a plush grey couch and armchairs, centered around a round coffee table. Natural light fills the room, showcasing the open layout that connects to a modern kitchen in the background. A ceiling fan is visible above for comfort.
Bungalow in Timonium
4.85 out of 5 average rating, 384 reviews

* 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.

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, 326 reviews

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!

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, 331 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, 154 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 kitchen features modern appliances, grey cabinetry, and a central island with seating. Light-filled from multiple windows, the space opens to a dining area with a wooden table and woven light fixtures, enhancing the spacious and functional design.
Bungalow in Cape May
4.97 out of 5 average rating, 152 reviews

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.

Superhost
A private hot tub is situated on a wooden deck, surrounded by lush greenery and a landscaped yard featuring decorative stones and stepping stones. Soft sunlight illuminates the area, creating a serene outdoor retreat.
Bungalow in Richmond
4.92 out of 5 average rating, 285 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, 673 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".

Top guest favourite
A charming bungalow is depicted with a welcoming front porch and neatly trimmed bushes. Trees surround the structure, providing a natural setting. A dog sits calmly in the grass, adding a sense of homeliness to the scene.
Bungalow in North Cape May
4.93 out of 5 average rating, 159 reviews

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

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!

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