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Waterfront Getaway w/ Pool + Beaches+ Hot Tub +BBQ

Unwind at this serene and secluded getaway—perfect for couples, small groups, families or anyone looking to relax by the water. This charming one-bedroom guest house offers comfort and style with a plush king-size bed, a fully equipped kitchen with a gas stove, and a spacious living area with a queen-size pullout sofa. Step outside to your private, oversized balcony overlooking the river—an ideal spot for morning coffee, al fresco dining, or winding down with sunset views and a glass of wine.

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

Brand-New Pool! Waterfront Bozman Village Home

Pets Welcome w/ Fee | 5 Mi to St. Michaels | Go Kayaking Experience classic Eastern Shore living at this 4-bedroom, 2.5-bath Bozman home — ideal for families, friends, and anyone craving a peaceful escape. The vacation rental boasts a fishing dock, a hot tub to unwind in the evenings, and acres of lawn where kids and pets can roam. Enjoy the spacious custom kitchen, gathering spaces, and thoughtful touches like shelves stocked with games. Head to Tilghman Island for even more adventure!

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.

Two Oysters House 2025 Remodel

The Two Oysters House finished renovations in 2025. The house is on the water with private (salt water) pool and dock situated in a peaceful country retreat in St. Michaels, Md just 2.5 mi. from the center of town (Inn at Perry Cabin and Museum). Bikes and kayaks are included in the rental rate. 4 bedrooms plus den 3 full baths. 2 Mastersuite with private bath. We prefer weekly rentals in the summer. 3nt.min stay. Pool/spa open in the summer, please check with us for exact dates.

Baydream Believer

BAYDREAM BELIEVER This home is a waterfront wonderland with plenty to do, from tubing and boating to fishing and crabbing directly from the dock. Relax by the pool or in the hot tub. Read under the trees as you swing in the hammock. Evening activities like stargazing and sunset watching. Three night minimum Labor Day Weekend to Memorial Day Weekend. Seven night minimum Memorial Day Weekend to Labor Day Weekend (inquire for less nights and will accomodate if available)

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 Family Retreat - mins from St. Michaels

Dive into luxury with a huge pool, relaxing spa, and outdoor hangout area complete with TV, fire pit, and comfy seating. Inside, cozy up by the fireplace on the massive couch, enjoy Sonos surround sound, and cook in the chef-ready kitchen. Fenced yard with a play area for little ones, breathtaking sunsets, and a private dock for crabbing and fishing—perfect for entertaining, unwinding, and making unforgettable memories with family and friends.

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!

Relaxing Retreat on the Hudson

Come escape to my 5-bed, 2-bath home on Hudson Creek! Featuring a deep pier with great crabbing, fishing, and boating, plus a bubbling hot tub and modern amenities throughout. Perfect for large groups, it comfortably hosts 15! Explore with complimentary kayaks, stay productive with WFH setups in every bedroom, and use my EV charger. Create unforgettable memories by the water.

Bankors Aweigh | an ESVR property

This 4-bedroom, 1.5-bathroom waterfront getaway features a character-filled interior and features a separate dining room. A foodie's dream, this well-equipped recently updated kitchen is space efficient. Retreat to the comfortably sized main bedroom that comes complete with spacious closets. Talbot County STR License STN-22-27