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
4.73 out of 5 average rating, 193 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
4.97 out of 5 average rating, 286 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
4.81 out of 5 average rating, 161 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.

Guest favourite
A modern kitchen featuring white cabinetry and a spacious island with a gas cooktop. A variety of kitchenware is neatly arranged on open shelves. The living area includes a comfortable orange chair and a soft rug, with natural light filtering through nearby windows.
Bungalow in Richmond
4.9 out of 5 average rating, 145 reviews

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!

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
4.81 out of 5 average rating, 110 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*

Guest favourite
Bungalow in Ocean City
4.87 out of 5 average rating, 143 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, 203 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, 416 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
Bungalow in Richmond
4.97 out of 5 average rating, 258 reviews

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.

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, 163 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.

Guest favourite
A single-family home with a brick exterior is surrounded by greenery. The inviting front porch is complemented by a stone pathway leading to a spacious outdoor seating area, featuring a fire pit and chairs for relaxation.
Bungalow in Queen Anne
4.95 out of 5 average rating, 100 reviews

Private bungalow with fire pit near Easton, Denton

- High-speed Internet - Premium Samsung washer and dryer - Fire Pit - Level 2 EV Charger - Two (2) cruiser bicycles - Memory foam mattresses - Full kitchen - Smart TV - Quiet, secluded space with easy access - 5 minutes to Denton - 15 minutes to Easton - 15 minutes to Centreville - 30 minutes to St. Michaels Located just minutes from both Easton and Tuckahoe State Park, you'll have endless opportunities for outdoor adventure.

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, 711 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 $106 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Chesapeake Bay holiday rentals include Wi-Fi 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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