
Cabin rentals near Chesapeake Bay
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Top-rated cabin rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness, and more.

Hideaway on the Bay: Waterfront Vintage A Frame
The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --
4.91 out of 5 average rating, 269 reviews
Waterfront Cabin: beach, kayaks, hot tub & firepit
Welcome to Fox Point Cove! Whether you’re looking for a relaxing weekend with family/friends or a quiet and inspiring writer’s retreat, you can find it here. Located a few hours from DC and Richmond, this 2.5 acre waterfront property is a world away! Enjoy coffee on the porch, time on our private beach, sunsets from the dock, and evenings by the fire. Soak in the hot tub, or take the kayaks out! We offer comfy mattresses and cozy linens, as well as high speed wifi and a fully stocked kitchen.
4.95 out of 5 average rating, 108 reviews
Ultimate Cabin Farm Stay Cape Charles
Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, feed the Alpacas, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.
4.96 out of 5 average rating, 264 reviews
6 acres of privacy - water access/firepit/kayaks
Enjoy a tiny house on a lot of land! Inside the home, you’ll have a king bed, full bathroom, full kitchen, and comfy living space. Outside, a short walk on our private trail that winds through 6 acres of woods brings you to our dock on the Rappahannock River. Enjoy fishing, kayaking (one single, one double), or just sipping a beverage and watching the beautiful nature and wildlife around you. At Camp Cottontail, you’ll find a secluded rustic retreat with the modern comforts of home.
4.96 out of 5 average rating, 113 reviews
Pizza Friday
Magnificent 26-acre waterfront property just off the Potomac River. This secluded, quiet waterfront oasis boasts four-bedroom and two-full baths with large picture windows offering panoramic water views from almost every room. The large updated kitchen features stainless appliances, ample cabinetry, granite countertops, and a breakfast nook. There is a large sunny dock, a pizza oven, kayaks and a canoe to enjoy the water. If you're looking for the perfect weekend getaway, this is it!
4.93 out of 5 average rating, 104 reviews
Waterfront cabin home - 9+ private wooded acres
Gunpowder Cabin is a peaceful getaway set on 9+ wooded acres and a private drive in Northern Maryland, just an hour from Baltimore. With a half mile of hiking trails, and over 600 feet of frontage on Octoraro Creek, there are numerous options for taking in the natural beauty: warm up by our two firepits, lounge in a hammock, take a dip in the river, or fish for trout from the shoreline. A secluded retreat that feels remote, but moments from the civilization you came to escape.
5.0 out of 5 average rating, 132 reviews
Covenant Cove (Cove Point Beach)
Nestled at the edge of the Chesapeake Bay, next to the iconic Cove Point Lighthouse, this charming cabin offers a peaceful and rustic escape from the everyday hustle and bustle. Situated in the serene surroundings of Cove Point, the cabin provides a perfect blend of comfort and simplicity, ideal for those seeking a quiet retreat amidst nature. One of the main highlights of staying at this cabin is its proximity to the private community beach, located just a short walk away.
4.88 out of 5 average rating, 111 reviews
Cabin on the Creek ~ Kayaks and Fire Pit
Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.
4.89 out of 5 average rating, 120 reviews
The Hepburn-Hot Tub & Fire Pit
The Hepburn is a beautifully renovated and decorated by home by Harlow Grey Homes. This meticulously restored glass cabin is located on over an acre of private grounds on a serene 75 acre lake. This is not a home for parties, loud events. The 10pm QUIET HOURS outside is mandatory! The separate seven-person hot tub is OPEN for the Fall/Winter season when the pool is closed. The private pool + built-in spa is open Spring/Summer
4.93 out of 5 average rating, 267 reviews
Dinna Fash-3 BR Waterfront Log Cabin
Welcome to “Dinna Fash,” our cozy waterfront cabin on the Little Wicomico River. Whether you need a change of scenery while working virtually with our high speed internet and fully equipped kitchen, or just some R & R, “Dinna Fash” is it! Bring your kayaks and paddle boards to explore the beautiful waterway that opens up to the Chesapeake Bay. Watch the boats troll by from our natural rock fire pit and comfy Adirondack chairs.
4.96 out of 5 average rating, 313 reviews
Bayfront Walk-Out Beach Home | Sunrise & Fire Pit
Wake up to sunrise views over the Chesapeake Bay in this true walk-out beach home. Step directly from the property onto a sandy, shallow shoreline via short, easy steps. The bayfront beach is ideal for wading, exploring, and spending time together by the water. This modern Panabode log cabin blends rustic charm with clean, contemporary comfort. Relax on the deck, in the hot tub, by the fire pit, or on the sand.
4.99 out of 5 average rating, 113 reviews
Peaceful Waterfront Retreat on The Bay
Escape to a serene waterside cabin with a private dock on quiet St. Leonard Creek, just an hour from Washington, DC. This rustic studio offers a cozy retreat for solo travelers, couples, or small families looking for peace and relaxation. Whether you're here to unwind, work remotely, or explore the outdoors, you'll find plenty to enjoy—including two kayaks, two canoes, and stunning waterfront views.
4.89 out of 5 average rating, 323 reviewsPopular amenities for cabin rentals near Chesapeake Bay
Cabin rentals with a hot tub

Walkersville Cabin
4.91 out of 5 average rating, 135 reviews
Cozy Waterfront Cabin Escape
5.0 out of 5 average rating, 60 reviews
StillFrame | Serene A-Frame + Hot Tub | 1hr to DC
5.0 out of 5 average rating, 20 reviews
2-bedroom lake-house with a magnificent view
4.81 out of 5 average rating, 214 reviews
Luxury Historic Waterfront Cabin
5.0 out of 5 average rating, 17 reviews
Old Log Cabin School House w/10 acres on the Bay
4.74 out of 5 average rating, 108 reviews
The Horseshoe Pond Fredericksburg (Woodford) VA
4.96 out of 5 average rating, 28 reviewsPet-friendly cabin rentals

Cozy Country Cabin
4.99 out of 5 average rating, 102 reviews
Relaxing Cabin Get Away Near Annapolis & DC
4.92 out of 5 average rating, 189 reviews
Cozy Cabin in Scenic Southern MD
4.88 out of 5 average rating, 121 reviews
Dyers Cove
4.83 out of 5 average rating, 118 reviews
Rest & Recharge, A-frame Cabin on Winery Grounds
4.94 out of 5 average rating, 199 reviews
*NEW * cozy wooded retreat 🌳 near Delaware beaches
4.93 out of 5 average rating, 142 reviews
Harrell’s Cabin
4.84 out of 5 average rating, 951 reviews
Log Cabin - Williamsburg Pet-Friendly, Heated Pool
4.79 out of 5 average rating, 111 reviewsPrivate cabin rentals

1765 Log Home in a Peaceful Setting
5.0 out of 5 average rating, 262 reviews
The Guesthouse at Downey Family Farm
4.94 out of 5 average rating, 149 reviews
30% off 30 Day Stays Blue Bird Tree House 1BR/Den
4.96 out of 5 average rating, 118 reviews
Waterfront Log Cabin | Kayaks, Arcade & Sleeps 12
4.93 out of 5 average rating, 82 reviews
Ocean Break
4.84 out of 5 average rating, 45 reviews
Beach Road Oasis, Tangier Island, VA
4.98 out of 5 average rating, 52 reviews
Parkside Log Cabin
4.97 out of 5 average rating, 92 reviews
Historic Cabins on the creek - tucked away.
4.94 out of 5 average rating, 79 reviewsLuxury cabin rentals

Secluded Log Cabin Escape on Private Pond & Acres
4.96 out of 5 average rating, 199 reviews
Stunning! River-Front Log Cabin Near Williamsburg
4.97 out of 5 average rating, 94 reviews
Exceptional Custom-Built Post & Beam Home
4.95 out of 5 average rating, 40 reviews
Waterfront pet friendly cottage!
4.67 out of 5 average rating, 12 reviews
City Cabin: DC, Hot tub, Game Room, Speakeasy
New place to stay
Maryland Vacation Rental w/ Private Pool & Dock
4.85 out of 5 average rating, 27 reviewsQuick stats about cabin rentals near Chesapeake Bay

Total vacation rentals
Explore 60 vacation rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

Verified guest reviews
Over 4,670 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Chesapeake Bay vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesapeake Bay rentals

4.9 Average rating
Chesapeake Bay stays are highly rated by guests—averaging 4.9 out of 5!
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- Cabin rentals United States
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