Holiday rentals in McDaniel

4.93 out of 5 average rating, 224 reviews

Home in Stevensville

Relax on Kent Island in 3 Bedroom Home w/Waterview

Enjoy your vacation in this Beautiful & Stylish 3 Bedroom Home with a view of the Chesapeake Bay from living room & kitchen! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 20 miles Baltimore- 45 Wash. DC- 50 Easton- 35 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions. This is a Non-Smoking House. Also No Pets, Parties or Large Groups (11 max). Book Today!

4.91 out of 5 average rating, 175 reviews

Flat in Saint Michaels

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.

4.98 out of 5 average rating, 278 reviews

Flat in Stevensville

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

4.99 out of 5 average rating, 176 reviews

Houseboat in Grasonville

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

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, 604 reviews

Guest house 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.

Guest house 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.

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

4.99 out of 5 average rating, 170 reviews

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!

Superhost

4.6 out of 5 average rating, 5 reviews

Pet-Friendly Waterfront House

Escape to this charming 2-bedroom waterfront home in Saint Michaels! Enjoy a perfect blend of relaxation and convenience, located just a short drive from downtown and Tilghman Island. With water views, a cozy atmosphere, and nearby attractions, this house is ideal for your getaway. Talbot County Licensure: STR-24-12

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Other great holiday rentals in McDaniel

5 out of 5 average rating, 10 reviews

Margaret Wells House - New

MarieRating, 5 stars4 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.

5 out of 5 average rating, 12 reviews

Home in Easton

Charming House, Quiet Neighborhood (Entire House)

DavidRating, 5 stars1 week ago

Nate's house was perfect for our purposes. The neighbourhood is very quiet and peaceful, but you are less than 10 minutes from grocery stores, restaurants and other amenities. The house itself was exactly as described, and had everything we needed, with plenty of space. It was clean, comfortable and well-equipped. Nate was a very responsive and proactive host. We would definitely try to stay here again if we are in the area.

Guest house in Grasonville

4.9 out of 5 average rating, 230 reviews

Eastern Shore Charm on Winchester Creek

CharlieRating, 5 stars1 day ago

Great host! Friendly and made us feel at home. Had tons of complimentary snacks and drinks, and gave us free muffins that were amazing.

Guest suite in Dunkirk

5 out of 5 average rating, 3 reviews

Pool-side chickens between D.C. and Chesapeake Bay

RyanRating, 5 stars3 days ago

Great stay for our large family! Booked for pool, and we swam every day! Also my kids thoroughly enjoyed the Atari! Was great getting to meet Luis and Laura and their son! Talked about booking next year!

5 out of 5 average rating, 11 reviews

Home in Shady Side

The Wise Quack 2 - A Taste of the Chesapeake Bay!

ToddRating, 5 stars1 week ago

The Wise Quack 2 is a cozy, clean Airbnb steps from the Chesapeake Bay, perfect for a relaxing getaway. Sidco’s warm hospitality, comfy beds, and thoughtful touches like the deep tub and hammock make it a gem. The quiet Shady Side location and quick host responses ensure a delightful stay.

Townhouse in Tilghman Island

5 out of 5 average rating, 44 reviews

Tilghman Island Waterfront Home w/Stunning Sunsets

Maggie Rating, 5 stars1 month ago

We loved it so much we are hoping to return again…hopefully sooner rather than later! It is PERFECT!