Holiday houses in Mayo Beach

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

Waterfront Chesapeake Bay Sunrises & Fishing Dock!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Searenity Stays, a Cozy Home

Walk to Chesapeake Bay, park spaces & playgrounds! Searenity Stays is nestled in a quiet neighborhood. It's only 3 blocks to Saunders Point Beach with a private community pier and beach. Big Pond is 3 blocks the other direction and has a playground and picnic tables. Maryland's natural shoreline woods are a short walk away (.4 miles) at Beverly Triton Nature Park. Mayo Beach is a 5 minute drive (2.3 mile walk), but be sure to check online first to see if an online pass is needed that day.

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

Luxury Modern Home on Water+Hotub- Annapolis 25min

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

Waterfront Cottage with Private Pier

Miss Kitty’s Place is a waterfront gem just off the South River! It is named after its original owner whose family built this quintessential bayside cottage in the 1960’s. Arrive by car or by boat, and enjoy the private dock for fishing, crabbing and viewing the AMAZING sunsets. Launch the complimentary paddle boards or kayak into the calm waters of Ramsay Lake. Walk to the two nearby public beaches, Mayo and Beverly Triton. We hope you enjoy your stay at the bay as much as we do!

Peaceful Coastal Escape | Water Views + Hot Tub

Unwind in a serene coastal retreat with calming water views and a wraparound porch designed for slow mornings and sunset evenings. Enjoy the hot tub, fire pit, and thoughtfully styled interiors—perfect for couples or small families. Set along the marsh for beautiful views and privacy, this home is ideal for relaxing and recharging. You’ll enjoy the entire upper level of the home, completely private and never shared. The lower level is locked and unoccupied during your stay.

The Cottage at Broad Creek

Your Private Waterfront Escape on Maryland's Eastern Shore Wake up to panoramic water views from your soaking tub. Kayak from the private dock, cook your catch in the chef's kitchen, then gather at your waterside fire pit and grill as the sun sets over the bay. Minutes from historic St. Michaels yet secluded enough to feel like your own sanctuary. Perfect for couples seeking both adventure and relaxation, whether celebrating a milestone or simply unplugging together.

Bay View Studio Apartment

Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private patio, or hot tub! 50 ft of waterfront make this private walk-out garden-level apartment nestled in a small wooded oasis near downtown Annapolis a gem. Walk to the marinas or the Sailing School to catch a water taxi to downtown or book a private sail or fishing tour. Walk to Port Annapolis to get some fresh baked goods at Black Market Bakery.

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.