
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

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.

Quiet cottage on wooded property
Secluded location for those who like nature and view of water through the trees. Walk down the hill to the creek to launch a boat, fish or watch the spectacular sunsets. The cottage has a sleeping loft with twin beds and a sofa bed in main living area. Furnished and equipped for short to longer stays close to Cove Point, Calvert Cliffs and across the river from PAX Naval Air station. Minimum stay is 2 nights. Just updated with cable tv and wifi. New flooring. Deep cleaned between guests.

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.

Light, Bright and Comfortable! No cleaning fee!
My place is close to family-friendly activities, nightlife and downtown Annapolis. You’ll love my place because it is bright, sunny, convenient and has lots of outdoor space. My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups. Bike, run, walk, ice skate (in winter) in the serene 300 acre Quiet Waters Park steps away from the front door. Enjoy a sports game at the Navel Academy, window shop through Historic Annapolis or hop on a boat.

The Yellow House: by Waterfront & Town Center
The Yellow House's perfect central location means everything is just a short walk from the front door -- whether it's down the hill to Urbanna Creek and the public Town Marina, to local restaurants and shops, the grocery store, or town park. TYH is also located in Urbanna's Historic District, within steps of a rare surviving 1760’s brick storehouse known as the James Mills Scottish Factor Store and two early 19th century dwellings -- Little Sandwich and the Gressitt House.

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.

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.
Popular amenities for bungalow rentals near Chesapeake Bay
Beachfront bungalow rentals

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

Bayside | Walk to Sand • Fenced Yard • EV Charger

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

New! Sandy Dunes on the Bay

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

SUN HOUSE: Artist's bugalow on a sanctuary dune

Waterfront Weekend Get Away.

Bayside Bungalow: Cozy North Beach Getaway
Private bungalow rentals

Behind the Red Door in Rehoboth Beach

Welcome to Mermaid Haven!

Mid century Ranch minutes to beach and base

Charming 3BDR Bungalow Near Annapolis

56th Street Beach Boys Bungalow

*Midterm/Longterm* Buckroe Beach Bungalow EV chrg

New, Chic River Bungalow in Historic District

Key West Bungalow by the Bay
Other bungalow holiday rentals

*Top Floor Bungalow* | Downtown Hampton | 1 BR

DC Colonial King Suite

1 Mile to Beach -BayHouse with Loft -Norfolk Va.

The Milton Bungalow - Midcentury Style Experience

Bungalow Sleeps 5, near the Choptank River

Beachside Cottage: Yard, Porch, Walk to BEACH

luxury Home Near Town Center

Our Home is Your Goal When You Play @ DE Turf
Other great holiday rentals near Chesapeake Bay

Waterfront FamilyFriendly Home Improved for 2023

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

Waterfront Guesthouse II on the Rappahannock

Private Country Beach Retreat

Bay cottage 🏖on the beach. Stunning views🏝

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

Hideaway on the Bay: Waterfront Vintage A Frame

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 £45 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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- Bungalow rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- Buckroe Beach
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
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- Old Dominion University
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- Chrysler Hall
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- USS Wisconsin (BB-64)
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