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WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse

Quiet waterfront cozy home w/ pvt pier, hot tub, kayaks, grill, massagechair & fire pit. Experience life on the river in a 2bedrm/1 bath-shower/3bed Retreat on a cove off the ChoptankRiver. About 15-20mins toHistoricCambridge/Restaurants/groceries. Easy day trips to St.Michaels/Tighlman/Oxford/Tubman; 75-90min drive to Ocean City/Rehoboth beach. Waterviews from beds. Relax in screened porch w/ waterviews. Watch sunrise/sunset in pvtpier/kayak/hottub. Bring fishing rods/crablines/baits-seasonal.

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

Welcome to Lucky Ducks Studio! Enjoy a fully renovated furnished studio in the heart of St. Michael's, MD. Located on Talbot Street in the historic 1850’s McMillian House, the 2nd floor studio offers couples a cozy "British" style experience that sleeps 4 (queen size bed & sofa that transitions to queen), a full bath with a claw tub and a gorgeous industrial style kitchen. Your steps away from the Miles River, shopping, museums, restaurants, breweries and wineries. Free WIFI and YouTube TV.

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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.

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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 kayak, 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.

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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.

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St. Michaels Waterfront-Pool/Kayak/Pier/Firepit

FALL BONUS. EARLY CHECKIN! Breathtaking views, private pool with baja deck, pier with boat slip, kayaks for 10, 4 bikes, and gas firepit by the water! Great for two families/multi-generations. Two primary bedroom suites and great water views from every room. Listing 347588 on vacation rental by owners. Extensive feedback on that site! 7 days during summer. PETS are $45 per pet per day Must get approval! Pool can be heated at a surcharge. Talbot County license: ST 809 GOL

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Panoramic water views

Tilghman Island Point of View. Our Island is perfectly situated on the Maryland crab and oyster trail. Step back in time to a slower lifestyle and observe the waterman’s way of life. Enjoy our two-bedroom coastal cottage and Island attractions. Enjoy the bird’s eye view of the local waterman in and out of the harbor seeking the days catch. Walk or kayak the shoreline. Take a stroll or ride a bike to Island attractions including all restaurants and shops. Arrive by boat or car.

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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

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Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

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Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8

HOT TUB!! WATERFRONT!! Relax with the entire family at this peaceful 3 bedroom fully remodeled private waterfront cottage on a quiet cove off the Choptank River/Chesapeake Bay. Enjoy the incredible views from your bed, from the large screened-in porch, from the oversized deck, from the hammock or double swinging chair out by the water! Launch a kayak right from the property and watch the gorgeous sunrises from the comfort of your bed!

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The Nichols House Cottage

This lovely guest cottage is located in the historic district of Oxford, walkable to town attractions and restaurants. While the main house is a registered historical property built in the 19th century Victorian style, the guesthouse is charming and well decorated with modern comforts. The cottage is completely independent from the main house. Make this your special place for a romantic getaway at any season of the year.

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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)

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Waterfront vacation home with private dock

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Waterfront, amazing views, pier, fishing/crabbing

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Tilghman Retreat: A house on the Chesapeake Bay.

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Cheerful 4-Bedroom Home in Beach Community

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• Peaceful Point • A relaxing waterfront retreat

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Magical Waterfront Home-Dock, Firepit, family fun!

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Storybook 3/3 cottage, FP, 1 blk to water

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"Goose Landing" Waterfront Retreat

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Crow’s Nest Cottage - Down Under: Chesapeake Bay

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⋘ Lakeside Apartment ⋙| Private+Cozy Setting |

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Couples River Retreat

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Charming Apt. in St. Michaels

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Cottage #1 Lighthouse First Cottage down driveway

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Loon Cottage on Leeds Creek

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