Cabin rentals near Chesapeake Bay

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.

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

Cabin is very charming, but rustic. Kitchen has full size frig, microwave, toaster oven, hot plate, toaster+ keurig. Coffee, condiments, soap & shampoo provided. There is a gas grill. Guests provide their qs sheets, towels, campfire wood & drinking water. A variety of dvd’s & games, hot water in & outside shower & tub. Tubes for floating provided, swim your own risk. Fire pit, creek is stocked. Steps to deck overlooking the creek.Trash goes home with guests, smoking on the decks only.

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.

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.

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.

True St. Michaels 6 Acre Waterfront w/heated pool

TREMEZZO STAY - Spencer Creek Cabin Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD. If you do not see availability for your dates or are looking to sleep more than 8 please visit our additional exclusive listings! Punch Point (sleeps 10) Chesapeake Mansion (sleeps 12) Ranch at Royal Oak (sleeps 12)

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...