
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.

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.

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 should extra toilets and showers be needed from April-November only.

🌅🎢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.

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.

Country House, Private and Comfy
Our Country House is the perfect place to gather with family and friends. Enjoy comfortable beds, upgraded bathrooms, a cozy TV room, and a spacious screened porch—ideal for relaxing after a day at the beach. Your dog will love the fenced backyard. Best suited for families. Conveniently located: Cape Henlopen State Park (9.9 miles), Rehoboth Beach (10 miles), Dewey Beach (11 miles), and Tanger Outlets (7.8 miles). Please note that travel times may be longer due to seasonal traffic.

Cozy waterfront getaway on the Bay
This 2 BR renovated waterfront home has a large, modern kitchen, comfy living rm and den, new HVAC, woodburning fireplace and hot tub. Hi speed FIOS & WiFi. Large recently rebuilt pier & L-shaped deck (2026) that is ideal for crabbing, fishing, birdwatching (osprey nest nearby), launching a kayak, or enjoying a cocktail during the season. Stunning waterfront and sunset views. Enjoy birdwatching, kayaking, or a soak in the hot tub.

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.

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!

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".

*Midterm/Longterm* Buckroe Beach Bungalow EV chrg
We welcome **MIDTERM / LONGTERM RENTAL** Bring the whole family to this newly renovated spacious bungalow with complimentary Electric Vehicle charging port and lots of room for fun. A cozy home away from home. Take a short walk to the beach or explore the many fun attractions in the surrounding area full of shopping, eating, entertainment, and so much more!
Popular amenities for bungalow rentals near Chesapeake Bay
Beachfront bungalow rentals

Bayside Bungalow: Cozy North Beach Getaway

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

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

The Barefoot Bungalow-Unit B-Steps From The Sand!
Private bungalow rentals

Beachside Cottage: Yard, Porch, Walk to BEACH

Light, Bright and Comfortable! No cleaning fee!

The Eventide at Serenity Lane

Quiet cottage on wooded property

The Yellow House: by Waterfront & Town Center

New Bungalow with view of the South River!

Entire 3 Bedrooms Single Bungalow in Arlington

Bungalow Sleeps 5, near the Choptank River
Other bungalow holiday rentals

City Tiny House | Near River | Getaway | King |

Key West Bungalow by the Bay

2 Full Baths, Clean, Comfy & Spacious!

Behind the Red Door in Rehoboth Beach

Private, and Cozy 3 Bedrooms Home - Faraja House

Pet-Friendly Downtown Beach Bungalow

Bethany Beach Retreat - 10 Minutes to Ocean

1st Floor 2 BR Cottage Walking to Beach
Other great holiday rentals near Chesapeake Bay

Long Beach Cottage, Hot Tub, Beachfront

Water's Edge Cottage | Luxury Retreat

Hideaway on the Bay: Waterfront Vintage A Frame

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Best View on the Northern Neck, Sandy Beach!

Historic Rousby Hall, Waterfront, Pool, Beach

Beach Front and 'Perfectly Placed'

Peace Point - Waterfront, Secluded, Home w/hot tub
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 $102 NZD per night before taxes and fees

Verified guest reviews
Over 3,440 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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- Bungalow rentals United States
- Chincoteague Island
- Virginia Beach Oceanfront
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- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- First Landing Beach
- Neptune's Park
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