
Cabin rentals near Chesapeake Bay
Find and book unique cabins on Airbnb
Top-rated cabin rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Cabin on Middle Creek - Myersville MD - Middletown
Park the car & walk across the creek on the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Great place to unwind & de-stress. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting

Sleepy Hollow Log Cabin
Sleepy Hollow Log Cabin at Beechnut Springs is nestled in the majestic Blue Ridge Mountains. A short distance from Rt 70 as you travel down scenic route 17 following a bustling trout stream to Beechnut Springs entrance. After you arrive & settle into your secluded cabin, you will find many unique activities & quiet places in this serene setting amid the wonders of quiet waterfalls, easy walking paths, a wildlife haven, natural running streams & "The Bog Shack". Welcome to Sleepy Hollow Log Cabin

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 --

Lakefront A-Frame cabin home, minutes to NJMP
Check my other listing in same area: www.airbnb.com/h/clubdivot Secluded Lakeside Location: Our A-frame cabin sits nestled among trees, right at the water's edge, offering unobstructed lake views, beautiful sunsets, and a private escape from the hustle and bustle of everyday life Modern Elegance: Step inside to discover a cozy and tastefully decorated living space with beautiful lake views. Perfect Getaway: For quality time with loved ones enjoying trails and other popular attractions

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
Welcome to The Lake House - our freshly updated 3 bedroom, 3 bath cabin on Lake Vista with views of the Patuxent River/Chesapeake Bay from the private pier. Enjoy everything Southern Maryland has to offer all within a 10 minute drive - Calvert Cliffs, Flag Ponds, Solomons Island - hiking, fishing, boating and beaches. Located just 90 minutes outside DC, The Lake House will become your new go-to retreat from the hustle. Come relax and make memories on the water with your family and friends.

Rest & Recharge, A-frame Cabin on Winery Grounds
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.

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.

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.

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.

Misty Hill Lodge-Frederick
Pets not permitted. This is a no smoking property, inside and out. Misty Hill Lodge - 2 BR, 2 BA, 1930's Log Cabin in Frederick will be the place where all your stress disappears as soon as you arrive. 5 wooded acres, Huge 29x29 Great Room, 80" Smart TV, Central AC/Heat. Built from American Chestnut trees that lined the property, (15min to downtown Frederick, 5 min to Middletown). The property features incredible wildlife.

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.

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.
Popular amenities for cabin rentals near Chesapeake Bay
Cabin rentals with a hot tub

Hot Tub, Fire Pit & Patio: A-Frame Stafford Cabin

Tranquil Timber Lodge

Luxury Historic Waterfront Cabin

Walkersville Cabin

2-bedroom lake-house with a magnificent view

Dreamcatcher Cabin ~Scenic views with BIG sky hues

*No Fees* Waterfront Cabin with Dock

The Black Log Cabin – Hot Tub/GameRoom/PetFriendly
Pet-friendly cabin rentals

"Elderberries" Chesapeake Bayfront Cottage

Harrell’s Cabin

Relaxing Cabin Get Away Near Annapolis & DC

Awesome private off grid cabin with creek view.

Cabin On The Cliffside

Modern Island Cabin

Dyers Cove

Cozy Cabin in Scenic Southern MD
Private cabin rentals

Chalet Style Home, private country setting

Cozy Country Cabin

Parkside Log Cabin

The Guesthouse at Downey Family Farm

Spruce Run Cabin, a wooded retreat on the mountain

1765 Log Home in a Peaceful Setting

Cabin with History On a historic 18acre homestead

The Boathouse on the Creek
Luxury cabin rentals

True St. Michaels 6 Acre Waterfront w/heated pool

Nature watcher's delight at the edge of the earth

Andrews House at Caboose Farm

Pizza Friday

One-of-a-kind Log Cabin with river access

Dock, Waterfront Fire Pit Life

The Hepburn-Hot Tub & Fire Pit

Exceptional Custom-Built Post & Beam Home
Quick stats about cabin rentals near Chesapeake Bay

Total holiday rentals
Explore 60 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at £38 per night before taxes and fees

Verified guest reviews
Over 4,470 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Chesapeake Bay holiday rentals include wifi 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!
Destinations to explore
- Rentals with outdoor seating Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- House rentals Chesapeake Bay
- Motorhome rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guest house rentals Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Beach apartment rentals Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Holiday home rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with a cinema Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Flat rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Cabin 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
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Town Point Park
- Nauticus
- First Landing Beach
- Virginia Living History Museum
- Old Dominion University
- Hampton University
- Chrysler Hall
- Neptune's Park
- USS Wisconsin (BB-64)
- Children's Museum of Virginia




