Places to stay near Chesapeake Bay Maritime Museum

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Top-rated vacation rentals near Chesapeake Bay Maritime Museum

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Top guest favorite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in Saint Michaels
4.97 out of 5 average rating, 192 reviews

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

Guest favorite
A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.
Home in Grasonville
4.95 out of 5 average rating, 306 reviews

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

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.

Guest favorite
The image captures a grassy park area bordered by water, featuring two historic cannons positioned on a brick pathway. Benches are placed nearby, and trees with budding leaves provide shade. In the background, an ancient-looking house is visible, enhancing the park's historic character.
Home in Saint Michaels
4.77 out of 5 average rating, 106 reviews

In Town St. Michaels Waterview Cottage

The magical John Bruff house is a beautifully restored 2 bedroom historic house sitting on the St Michaels harbor and Town park, with amazing water views from every room. It is a short walk to parks, museums, shops, restaurants, Town pool, tennis courts, library - almost everything in Town! Perfectly suited for a small family, 2 couples, or a romantic getaway. Rates vary by season, and whether stay is weeknight or weekend. Stays of a week or longer are discounted, as are "last minute" bookings.

Top guest favorite
The living room features a chandelier, a decorative mirror above the fireplace, and a cozy seating area with two armchairs and a chaise lounge. A colorful area rug covers the floor, while a small table and lamp provide additional lighting.
Home in Saint Michaels
4.96 out of 5 average rating, 209 reviews

Historic Berkeley Hall in the heart of town

Berkeley hall is centrally located in historic Saint Michaels. Park your car and walk to everything! Great shops, restaurants and 3 blocks to the water. First floor includes a high ceiling parlor that connects to a lovely side porch and large kitchen. There is a mahogany staircase that takes you to the 2nd floor that has 2 master suites. One has a king bed the other has a queen bed w/ ladder to loft which is best for kids -has a twin size futon sofa bed. Perfect home for a romantic getaway.

Top guest favorite
Apartment in Saint Michaels
4.92 out of 5 average rating, 225 reviews

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 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.

Guest favorite
An aerial view captures the expansive property, featuring a large home surrounded by lush green lawns and mature trees. A heated in-ground pool is visible in the backyard, adjacent to a serene water body, with an expansive landscape enhancing the tranquil setting.
Cabin in Saint Michaels
4.99 out of 5 average rating, 123 reviews

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 rentals in St. Michaels, MD. We also own Tilghman Island Inn, a waterfront destination specializing in group retreats, weddings, and private events. 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)

Top guest favorite
A bright yellow building features large blue shutters and a welcoming entrance. A sign is placed outside, and vibrant flowers border the steps. In the background, another structure is visible, along with flags proudly displayed.
Apartment in Saint Michaels
4.97 out of 5 average rating, 151 reviews

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

Top guest favorite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville
4.99 out of 5 average rating, 352 reviews

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Top guest favorite
A serene waterfront scene is framed by a sprawling tree. Boats are moored along the docks, with calm water reflecting the sky. Quaint buildings line the shore, and a bench is positioned on the grass, inviting quiet contemplation of the picturesque surroundings.
Cottage in Saint Michaels
4.97 out of 5 average rating, 293 reviews

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

Top guest favorite
A charming blue cottage is depicted with a gabled roof and white columns framing the entrance. Lush green bushes line the pathway, providing an inviting approach. Clear blue skies and tall trees are visible in the background, enhancing the peaceful setting.
Home in Saint Michaels
4.98 out of 5 average rating, 112 reviews

SM's Premier Rental Heated Pool (opens 4/3)

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.

Top guest favorite
A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.
Cottage in Easton
5 out of 5 average rating, 124 reviews

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

Top guest favorite
A small historic home is shown from the front, featuring light beige siding and white trim. A welcoming porch with potted plants is visible, alongside two chairs and a table. The door is painted in a soft blue, framed by large windows on the upper floor.
Home in Saint Michaels
4.89 out of 5 average rating, 233 reviews

Small Historic House Downtown St Michaels

Small historic home in downtown St Michaels, walking distance to Talbot Street and all surrounding restaurants and shops. Your reservation includes the entire first floor; the second floor is unoccupied and not used. Maximum for 2 people and one vehicle. Holiday and special event weekends are priced at a higher rate, and the local Talbot County accommodation tax is collected prior to access to house.

Popular amenities for vacation rentals near Chesapeake Bay Maritime Museum