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Tranquility on Tilghman Island – Wide Water Views

Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shore, or lounging by the pool with a good book. Just minutes from charming St. Michaels, this 4-bedroom retreat blends coastal charm with modern comfort — perfect for families, friends, or a romantic getaway. In the evenings, grill, gather around the firepit under the stars, and let the day fade away in the bubbling hot tub. Guests love the spacious layout, the dreamy screened-in porch for

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.

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!

Crab Alley | Waterfront Home + Hot Tub + Game Room

BNB Breeze Presents: Crab Alley Welcome to Crab Alley, a stunning Bayfront home nestled in the serene surroundings of Chester, Maryland. This beautiful property offers a perfect blend of relaxation and adventure, making it an ideal getaway for families or groups of friends. With its prime waterfront location, guests can enjoy breathtaking views and easy access to water activities right from the comfort of their home. - HOT TUB! - Boat Dock - Deck w/ Bay Views - Game Room - Outdoor Dining table

Charming Annapolis Water View Home

Floor-to-ceiling windows overlook the expansive Chesapeake Bay 100ft away. Water views from most rooms plus treehouse vibes. 4 bedrooms + 4 full bath. Custom luxury upgrades, new appliances. Pull out daybed +2 folding queen mattresses, rustic leather sectional sofas can sleep 4 more (14+total), outdoor grills, covered balconies, hot tub, kayaks. Access to community fishing/crabbing piers/beach/picnic area. Close to beautiful Thomas Point & Quiet Waters park. A unique escape for nature lovers!

Waterfront Oasis: SaltwaterPool&HotTub&PrivateDock

Cattail Cove: Your perfect riverside escape! Nestled on 4 scenic acres along the river, our property offers a peaceful respite for family&friends. Sip your coffee overlooking the river as bald eagles dive for their breakfast, and then relax in the heated saltwater pool before crabbing from our brand-new private pier! Included Amenities: -Saltwater Pool: seasonal -Hot tub open all year! -Stone Fire Pit -Kayak, paddle board, canoe -Private boat launch area Max Guest Count is 13 total people

Crew's Quarters | an ESVR property

1/2 Mile to Historic District, Pickleball Court, 3 Private Suites! Step into this idyllic, uniquely Eastern Shore Nanticoke mid- century home, perfect for friends and family, especially for multiple couples looking to be a short drive into the historic town of St. Michael's . This spacious 3-bedroom, 3.5-bathroom home was renovated top-to-bottom in 2022 with an open-design floor plan, formal dining room, and large entertainment spaces. Extra large windows through-out provide wonderful views

Sunset's Edge - Family Retreat Near St. Michaels

Sunset’s Edge delivers stunning water and sunset views, water access, and relaxed comfort. Just minutes from two of Talbot County's most charming towns – St. Michaels and Easton – this property is designed with families in mind. Features include pool (seasonal), kayaks, basketball net, boating dock, pool toys, backyard BBQ, screened-in gazebo, hammock by the water's edge, fire pit and heated hot tub (year round). Booking requires signed rental agreement, or may be subject to cancellation.

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Waterfront Hot Tub, Fire Pit & Views

Sink into the hot tub and watch the sun set over the Chesapeake Bay. This waterfront home in Chester has everything you need to unplug — a 270-degree sunroom with stunning water views, a fire pit for evening hangouts, a cozy indoor fireplace, and two comfortable bedrooms that sleep up to 8. The full kitchen is ready for group meals, and the sofa bed adds extra space. Minutes from Kent Island restaurants and the Bay Bridge. Annapolis and the Eastern Shore's best spots are an easy drive.

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

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!