Holiday houses in Saint Michaels

Apartment in Saint Michaels

4.91 out of 5 average rating, 175 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 size 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.

Houseboat in Kent Narrows

4.97 out of 5 average rating, 150 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

5 out of 5 average rating, 170 reviews

Home in Shady Side

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. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

4.99 out of 5 average rating, 121 reviews

Guesthouse in Cambridge

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

5 out of 5 average rating, 117 reviews

Home in Leonardtown

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.

5 out of 5 average rating, 102 reviews

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!

4.99 out of 5 average rating, 603 reviews

Guesthouse in Easton

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Cottage in Saint Michaels

4.97 out of 5 average rating, 164 reviews

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.

Guesthouse in Stevensville

4.99 out of 5 average rating, 278 reviews

Waterfront Getaway - 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.

Cottage in Saint Michaels

4.98 out of 5 average rating, 237 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.

4.98 out of 5 average rating, 101 reviews

SM’s Premier Rental Heated Pool opens 4/11/2025

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.

Guest suite in Saint Michaels

4.78 out of 5 average rating, 358 reviews

Gorgeous Cottage: Easy Walk into St Michaels Town!

Gorgeous, sunny former artist loft with great views. Across from Miles River & harbor. Walk to town! Shopping, brewery, winery, museum, restaurants await! Located in historic Bentley Hay, the lodge is perfect for relaxing walks while runners and bikers explore spectacular sights, including the nearby St Michaels Nature Trail. Or rent a kayak and explore San Domingo Creek! NO PETS OR SMOKING. 4 GUESTS MAX BY LAW. Talbot Co License STR-716-KIM

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Saint Michaels holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Saint Michaels

Houseboat in Inner Harbor

4.99 out of 5 average rating, 76 reviews

Flohom 1 | Breathtaking Skyline 360° Views

MackenzieRating, 5 stars3 weeks ago

Overall this rental was a great stay! The furniture was comfortable and the environment was very nice. It’s an absolute beautiful location and all the windows make it feel like you’re on a serene vacation. It was clean and the hosts gave very clear check in and check out instructions. The rooftop fireplace and all the other ammenities made it feel luxurious, but it still had a homey feel. The only “downside” I would say is that it’s a bit pricey, and the cleaners were leaving right at 3:00 as we were arriving, but I would definitely recommend FloHom to a friend!!

5 out of 5 average rating, 6 reviews

Historic Retreat in St. Michaels

MaryRating, 5 stars1 week ago

Dennis’ house is in an awesome location and close to everything! We really enjoyed having a drink and relaxing on the back screened in porch. Dennis was quick to respond to the couple of questions that we asked! Loved all the amenities that he provided! We had a wonderful time, and will definitely be returning! Thank you Dennis!

5 out of 5 average rating, 17 reviews

Cottage in Oxford

Sailor's Cottage - Private Waterfront

ChristopherRating, 5 starstoday

We recently stayed at this beautiful Airbnb tucked away on a secluded property in Oxford, and it was exactly the reset our family needed. The house was spotless, cozy, and surrounded by nature—offering the kind of quiet you don’t realize you’ve been craving until you hear it. What truly made this stay exceptional were the hosts. We arrived by boat at a nearby marina, and due to our boat’s deep draft, they picked us up to bring us to the house. That extra effort made all the difference, especially with a group that included kids and family coming in from different ends. The home felt like a retreat—private, peaceful, and welcoming. It gave us a much-needed chance to reconnect, recharge, and create some lasting memories. We’d absolutely stay again and recommend this home to anyone looking for an escape from the hustle without sacrificing comfort or kindness.

4.98 out of 5 average rating, 63 reviews

Barn in Queenstown

Waterfront Modern Guest Barn

ElaineRating, 5 stars1 month ago

Overall, I enjoyed the place. The barn was minimalistic and nice for photos. The best part was the waterfront view. The house was very clean and pretty kid friendly (a few high chairs included). The kitchen had the bare minimum to cook and grill with but I wouldn’t say it was fully stocked. I would say in general that we enjoyed our stay. The kayaks were wonderful.

5 out of 5 average rating, 10 reviews

Margaret Wells House - New

MarieRating, 5 stars3 days ago

Beautiful historic restoration in an equally beautiful area. House is comfortable, clean quiet, and spacious. Perfect location for a trip to St. Michael’s.

4.75 out of 5 average rating, 4 reviews

Crew's Quarters | an ESVR property

CampbellRating, 5 stars3 months ago

Great place to stay for a girls get away!!! The place was gorgeous and beautiful laid out. The host was extremely responsive throughout our stay with any questions or requests for recommendations. The process to check in/out was extremely easy. The town of st michaels is beautiful, quaint and plenty to do! Lots of good restaurants, walking trails and beautiful views of the water in town. Thanks for a great stay!