Lóistíní saoire ar cíos i dteach in St. Michaels

Waterfront, Dog-friendly, Hot Tub, Peleton

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

River Front house / dock/hot tub

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

Soul Oasis - home on the Chesapeake Bay

Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Historic Rousby Hall, Waterfront, Pool, Beach

**Heated pool open to Nov 2. Thanksgiving chef dinner options** Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee additional).

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”). And be sure to visit our sister property, White Point Cottage!

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.

Shipwrights Cottage in Town!

Charming historic cottage within walking distance to all St. Michaels has to offer! Relax & enjoy the sights of town from your front porch! Once a working shipwrights cottage, this home is 2 stories with a 1st floor full kitchen, combo living-dining room, den with queensize pullout couch & full bath. The 2nd floor has 2 bedrooms & a full bath. Both bedrooms have vaulted ceilings & ceiling fans. The primary bedroom has a private sitting balcony. Walk to shops, restaurants & waterfront!

Waterfront Farmhouse Meets Modern Luxury

Enjoy all that the Eastern Shore has to offer while staying at the neoclassical 19th-century "Osprey's Reach" farmhouse. Osprey's Reach blends the original character of Kent Island with modern comforts of a full house restoration, all while enjoying stunning sunsets over the Chesapeake, from the private dock or poolside. Kent Island is centrally located for short day trips to Annapolis, Easton, St. Michael's or Chestertown, with family-friendly dining and shopping options on-island.

SM’s Premier Rental Heated Pool (closes 10/28)

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

Grace Cottage, Saint Michaels Walk to everything!

Welcome to Grace Street Cottage with a newly renovated kitchen! Located in the heart of Saint Michaels. Walk to shops, restaurants and experience the best of the Eastern Shore. This cottage has all you will need for a perfect getaway. Sit by the fire pit and grill out or take a few steps to Talbot Street where your dining options are endless! Pack your bags and head to the shore! The experience awaits you!