Cabin vacation rentals in Chesapeake Bay

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Top-rated cabin rentals in Chesapeake Bay

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Guest favorite

Cabin in Lewes

4.94 out of 5 average rating, 105 reviews

*NEW * cozy wooded retreat 🌳 near Delaware beaches

Come relax after a busy beach day at the ⚓️Admiral’s hideaway⚓️. A newly renovated 2BR/1bath Villa situated peacefully in an acre of private woods in Lewes, DE. A perfect getaway for a couple or small family visit near all the beach attractions. The hideaway is close enough for easy access yet far enough for residents to sleep undisturbed by traffic noises. Surrounded by nature🌲, the landscaping offer a priceless sense of tranquility ✨ like camping 🏕 but with all the comforts of being at home.

Guest favorite

Cabin in Lusby

4.93 out of 5 average rating, 198 reviews

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 --

Superhost

Cabin in Leesburg

4.94 out of 5 average rating, 370 reviews

100 Acre Wood

🌳100 Acre Wood🌳is the perfect magical getaway🌻our cabin is tucked away in the woods on a 100 acre property in the❤️of historic Loudoun County.Located in the charming village of Lucketts, known for our BEAUTIFUL WINERIES🍷FAMOUS ANTIQUE SHOPS, FINE DINING & CRAFT BREWERIES🍻The Potomac River, C&O Canal, Appalachian &WO&D Trails, Sugarloaf Mt. & Harpers Ferry are all just a few miles away.Come relax, unwind & enjoy our peaceful woods& wildlife🐾We are approx 1 hour to DC & 1/2 hr to Dulles✈️

Top guest favorite

Cabin in Chestertown

4.98 out of 5 average rating, 234 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

Guest favorite

Cabin in Colonial Beach

4.95 out of 5 average rating, 153 reviews

Summer Perfect, Water Front A-frame on Winery

This serene cabin is on the Ingleside Vineyard's property. Have a glass or two of wine and walk around the vineyards and then retreat to your own private a-frame cabin oasis. A beautiful view of the Roxsbury Estate where abundant wildlife can be viewed all around the property and the pond is stocked and ready to be fished. Within driving distance to wineries, Stratford Hall, George Washington & James Monroe's birthplace, Westmoreland State Park, and the beach town of Colonial Beach.

Guest favorite

Cabin in Cape Charles

4.96 out of 5 average rating, 171 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, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Guest favorite

Cabin in Upperco

4.93 out of 5 average rating, 124 reviews

The Guesthouse at Downey Family Farm

Cozy yet spacious renovated log cabin on our small farm in Maryland's picturesque countryside. Enjoy a relaxing stay in the country, where you can get to know the farm animals and enjoy eating outdoors under the pavilion. Large bedrooms, two bathrooms, great Wi-fi, and and fully-equipped kitchen and washer/dryer make this a great place to stay with your family. The Guesthouse is conveniently located with easy access to I-795, and is 35 minutes from BWI Airport.

Guest favorite

Cabin in Reedville

4.97 out of 5 average rating, 255 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.

Guest favorite

Cabin in Lusby

4.9 out of 5 average rating, 262 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.

Superhost

Cabin in Goldsboro

4.85 out of 5 average rating, 145 reviews

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

Wigwam Lodge is an experience nestled in a pine & hard wood forest with rural privacy. Incredibly spacious decks. Surround Forest Views inside and out! 5-min from Choptank river, 20-min from Historic Denton, Irish Pub & Grocery, 1hr from the beach. Easy PARKING 10ft from the front door. Solid WIFI! Click “Show More” Below to SEE ALL Deets...

Top guest favorite

Cabin in Deltaville

4.97 out of 5 average rating, 288 reviews

"The Little Red Cabin" aka The Galley

Called the "The Galley". This is the first cabin built on the property. Right on the water with views of the Bay and beach. Galley kitchen, bedroom, small bathroom with shower, family room with a fireplace and dining area. Big screened in porch w/ fabulous breezes. Literally, right on the water!!! NO PETS. Parking for 1 car.

Guest favorite

Cabin in Smithfield

4.89 out of 5 average rating, 141 reviews

Wickline Cabin on Moon Creek

The Wickline Cabin is a beautiful 3 bedroom waterfront cabin where you can sit out on the back porch and take in the scenery, take a ride in a canoe or kayak , do a little fishing, kick up a fire, or just relax in the hot tub. The cabin is not far from downtown Smithfield which has many small shops and boutiques!