Semesterboenden nära strand i Talbot County

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.

Secluded water, private sitting room, full bath!

Come by land or by Broad Creek! 125' dock. 1000' waterfront. 2 miles from St. Michael's. A perfect getaway for discerning guests. Ask to moor a small vessel (sorry, no trailers). Natural, secluded, private entrance. Ideal kayaking, biking and walking. Eagles, ospreys, herons, ducks, turkey, fox, rays, crabs, oysters... and when very lucky, dolphins! Hosts available for convenience, but not in your space. *PET: If breed preapproved, $90/visit up to 4 days for ONE small dog. $15/day thereafter.

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

River Guest Suite w/ Pool, Beach, Private BoatSlip

Enjoy some rest & relaxations on the river with an unbeatable sunset! This guest suite offers 2 private bedrooms & a private bathroom suitable for two couples or a family! It also includes a large private living room with a 85 inch flatscreen TV & a private bar! In addition a newly added full indoor private kitchen. As well as a pull out couch that becomes a bed, size full. Your stay comes with a personal escort from our farm dog, Reef! He’s an old yellow Labrador who loves making new friends!

• Peaceful Point • A relaxing waterfront retreat

Welcome to Peaceful Point! Come enjoy the beauty of the water and the serenity it brings at Peaceful Point. This brand new remodel is fresh on the market with 3 bedrooms, 2 bathrooms, and custom great room with vast views of the Choptank River from every seat. Enjoy the screened in porch over looking the cove, a vast yard, deck and pier to crab and fish, as well as kayak and paddle board. Privately located yet only 20 minutes from restaurants + shopping. Come relax with the family at PP!

Waterfront | Swim Spa + Sauna + Beach + Game Room

Escape to Oyster Bay Getaway, a stunning 4-bedroom waterfront retreat designed for relaxation and fun. Enjoy serene water views throughout the home, unwind in the swim spa or sauna, and cozy up by the indoor fireplace. Step outside to a private dock and fire pit perfect for evenings under the stars. The garage game room (unconditioned) and indoor lounge with poker table make this the ideal getaway for families and groups seeking comfort, entertainment, and a true waterfront experience.

Waterfront Modern Guest Barn

Find peace and reconnect with nature at this award winning guest barn. With its simple geometry and bucolic setting overlooking a quiet river of the Eastern Shore, this gem at the edge of a farm field could easily be mistaken for a working barn. But when you slide open the pair of two-story barn doors, you find a beautiful modern guesthouse full of light from the wall of windows facing the river. The setting is incredibly peaceful, and is a wonderful romantic escape or family getaway.

Saint Michaels Waterfront Home

This beautiful waterfront home sits just over the bridge entering St. Michaels. Two large bedrooms, two full bathrooms, and Two sofas make this a very spacious for a large amount of guests. 1 minute to St. Michaels, 7 minutes to Easton and 30 seconds (right around the corner) to The Oaks Wedding Resort. Lots to do including kayaking, paddle boarding, biking or just taking in the views and wildlife. Great restaurants and local shops within minutes from this house! ST-739-YOS

Magical Waterfront Home Dock, Firepit, Family Fun!

Heron's Rest is a stunning home w/ arguably the best water views in Cambridge from nearly every room, expansive patio, fire pit and dock - a peaceful place to gather with family and friends. Incredible location to explore the stunning and historic Eastern Shore and charming historic Cambridge. Easy drive to the Atlantic beaches--you CAN have it all- kayak, fish, birdwatch, explore Blackwater Wildlife Refuge, Easton, St. Michael's. Rare location w sunset and sunrise views!

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.

Stunning Chesapeake waterfront home

Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. Enjoy Town Creek and Tred Avon water views from every room and angle. Gorgeous sunsets from the wraparound porch, stargazing and fishing from the dock. Walk to Morris Street for a relaxed coffee, stroll through Town Park, or take the Ferry to St. Michaels. The Town of Oxford has issued short term rental license # STR25-06 for this property.

Charming Studio in the heart of St. Michael's, MD.

Welcome to Lucky Ducks Studio! Enjoy a renovated, private 2nd-floor studio in the heart of St. Michaels, located on Talbot Street in the historic 1850s McMillan House. Our cozy British-inspired retreat sleeps 4 with a queen bed, queen sleeper sofa, full bath with a charming clawfoot tub & gorgeous industrial-style kitchen. Best of all, you're steps from the Miles River, restaurants, shops, museums, breweries & wineries. Free WiFi & YouTube TV!