
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.

Quantico 2BR Home ~Train Potomac River Graduations
This 1925 Bungalow is a relaxing space whether visiting Quantico for TBS/OCS/FBI graduations or sightseeing. Amtrak and VRE train stop under 5 minute walk direct to Alexandria, Crystal City, or DC (Union Station). In town you can fish, watch the sunset at the Potomac River, visit restaurants, or drive 5 minutes to the golf course (open to public). For DoD Cardholders it is 7 min walk to theater/gym/bowling. Town access is through military base. REALID is needed to use the highway to town

A Slice of Paradise: Bowers Beach
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.

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.

Reel Lucky on Lossing - Walk to Beach/Pet Friendly
3 bed/2 bath bungalow centrally located on "the Point" and walking distance to the beach and downtown Colonial Beach! Relax on the screened-in front porch. Perfect for both family and friends' gatherings, with two TVs and a kitchen ready for cooking. There is an outdoor shower and a shed with beach chairs etc. Monthly/weekly rentals available and there are restaurants, breweries, wineries, and a tiki bar nearby. It is close to Dahlgren and around 2 hours from DC. 10% military discount.

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.

Hilltop @ Shiloh
Hilltop sits on a park-like estate. This NEWLY REMODLED Bungalow is part of a charming duplex, offering a private entrance and exclusive outdoor seating. Enjoy stunning views of rolling hills, ponds, and lush landscaping. Stay and refresh your soul in our peaceful cottage or explore! Close to breweries, wineries, the C&O Canal for biking and hiking, and antique shopping at the popular Lucketts Store. Just 11 miles to historic Leesburg, VA, Morven Park, or 15 miles to Frederick, MD.

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

A Block to Beach | 5 Beds, King Suite, Walkable

New! Sandy Dunes on the Bay

Waterfront Weekend Get Away.
Private bungalow rentals

The Yellow House: by Waterfront & Town Center

Bethany Beach Retreat - 10 Minutes to Ocean

Original Ocean City Cottage with Hot Tub

New, Chic River Bungalow in Historic District

Cozy shore bungalow

🌅🎢Bungalow 1 block to boardwalk on 4th st!

New Bungalow with view of the South River!

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

*Top Floor Bungalow* | Downtown Hampton | 1 BR

The Purple Pad - Ocean City MD beach block cottage

Behind the Red Door in Rehoboth Beach

Artist's Bungalow-Walk Metro/Parking

*Midterm/Longterm* Buckroe Beach Bungalow EV chrg

Charming Bungalow in the heart of Carytown

The Milton Bungalow - Midcentury Style Experience

Bungalow Sleeps 5, near the Choptank River
Other great vacation rentals near Chesapeake Bay

Private romantic pet friendly waterfront cottage

Peaceful Haven: nature & charming town

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

Waterfront Guesthouse II on the Rappahannock

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Waterfront Cottage Getaway Views/Kayaks/Fire Pit

Coastal Waterfront 1 Bedroom Cottage

Water's Edge Cottage | Luxury Retreat
Quick stats about bungalow rentals near Chesapeake Bay

Total vacation rentals
Explore 40 vacation rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay vacation rentals start at G$14,640 GYD per night before taxes and fees

Verified guest reviews
Over 3,340 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Chesapeake Bay vacation 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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- Bungalow rentals United States
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