
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 --

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.

Romantic Cabin. Waterview. Hot Tub. Gas Firepit.
Unplug and unwind at this luxury retreat in the hills of Airville, PA - just 1 hour from Baltimore and 40 minutes to Lancaster. Soak in the hot tub, relax by the gas firepit, or dine al fresco on the deck while enjoying the sound of the creek. Complete with a wood-burning firepit for cozy evenings under the stars or morning coffee with a view of the creek. Featuring 3 queen beds, luxury linens, and spa-quality toiletries, it’s your perfect escape - with all the comforts of a boutique hotel.

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.

Dinwiddie Couples Getaway- Wells Cabin @WeldanPond
Wells Cabin @Weldan Pond is a beautiful new space designed for couples who love to relax, enjoy the outdoors (hike, fish, trail bike, & more), & marvel over beautiful views. The Cottage has a full kitchen, a large king bedroom, a bright, window filled sitting area, and a new deck overlooking Upper Weldan Pond and acres of healthy, natural hardwood forest with nearly 4 miles of trails to explore. You'll also love just enjoying the deck and the beauty of the Virginia countryside.

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.

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.

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

The Little Stone Mill of Historic Fredericksburg

Waterfront Cabin on the Chesapeake

Walkersville Cabin

2-bedroom lake-house with a magnificent view

Dreamcatcher Cabin ~Scenic views with BIG sky hues

The Creek House: Waterfront with Hot Tub & E-bikes

Wickline Cabin on Moon Creek

*No Fees* Lake Cabin with Private Dock
Pet-friendly cabin rentals

*Private Waterfront Retreat w/3 Cabins Close to DC

Harrell’s Cabin

Lakefront A-Frame cabin home, minutes to NJMP

Cabin on the Creek Large Outdoor Firepit

Spruce Run Cabin, a wooded retreat on the mountain

3 levels *Luxury A-Frame Cabin, Lake View/Hottube

Modern Island Cabin

Rustic Chic Cabin Hideaway
Private cabin rentals

"ON THE ROCKS CABIN" the perfect getaway for 2!

Riverside R&R: Cabin, Dock, Kayak & Game Arcade

Creekside Cabin | Sauna&Fire Pit

Chalet Style Home, private country setting

Parkside Log Cabin

The Guesthouse at Downey Family Farm

1765 Log Home in a Peaceful Setting

1 BR The Blue Bird Tree House cabin!
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

Maryland Vacation Rental w/ Private Pool & Dock

The Hepburn-Hot Tub & Fire Pit

Beachfront Escape with Horizon Views of the Bay
Quick 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 $28 CAD per night before taxes and fees

Verified guest reviews
Over 4,210 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Chesapeake Bay vacation 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
- Waterfront rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- House rentals Chesapeake Bay
- RV rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with a home theater Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Condo rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Loft rentals Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washer and dryer Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Cabin rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Assateague Beach
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Outlook Beach
- Kiptopeke Beach
- Piney Point Beach
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- James River Country Club
- Wilkins Beach
- Little Creek Beach
- Wallops Beach
- Snead Beach




