Holiday rentals with a washing machine and dryer in St. Michaels

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.

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

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!

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.

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

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.

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

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!

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.