Cabin vacation rentals in Chesapeake Beach

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 --

Value · Family · Backyard

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.

Family · Value · Quiet

Ocean Break

Your peaceful retreat by the beach. This cozy, private space is located 40 steps up, giving you a quiet, elevated setting where you can pause, breathe, and truly unwind. Surrounded by a peaceful coastal atmosphere, it’s a welcoming place for rest, reflection, or simply a relaxing getaway. While it feels like a hidden escape, you’re still just 10 minutes from the shops and restaurants in Prince Frederick and only 20 minutes from the lively waterfront of Solomons Island and the iconic Tiki Bar.

Value · Location · Condition

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 rentals in St. Michaels, MD. We also own Tilghman Island Inn, a waterfront destination specializing in group retreats, weddings, and private events. 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)

Family · Location · Condition

Black Luxury Cabin Fire Pit•Game Room.10 Guests

Nestled in a quiet country setting our home offers quick access to state parks and beaches, desirable Solomon's Island, and a retreat from the world. Guests can expect a welcoming stay with all your essentials for a long or short term visit plus extra touches to make your experience memorable. What do guests love most about our home? Guests love our country setting - life slows down and the rush of our daily lives slips away. Our space is designed for a relaxing and no-stress get-away.

Location · Value · Pool

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!

Location · Family · Grill

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.

Family · Value · Hiking

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.

Value · Location · Outdoor spaces

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.

Family · Value · Bathroom

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.

Family · Value · Air conditioning

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.

Location · Family · Condition

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.

Family · Location · Kitchen