Vacation Rentals Places to Explore in St Michaels, MD
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Places To Stay, Vacation Rentals, Pool, Waterfront | 205 S Talbot St, St Michaels, MD 21663, USA
Flaneur, The Vacation Rental Company
The idea for Flaneur, The Vacation Rental Company, came from observing the vast differences in the guest expectation and what they were actually receiving in Maryland vacation r…
Explore placePlaces To Stay, Amenities, Pet-friendly, Pool, Waterfront, Vacation Rentals | 108 N Talbot St, St Michaels, MD 21663, USA
Chesapeake Bay Real Estate Plus
Find your perfect escape on Maryland’s Eastern Shore.
Explore placeLodging, Places To Stay, Vacation Rentals | 217 S Morris St, Oxford, MD 21654, USA
Nichols House
This lovely guest cottage is located in the historic district of Oxford, walkable to town attractions and restaurants. While the main house is a registered historical property b…
Explore placeVacation Rentals, Places To Stay | 201 Green St, St Michaels, MD 21663, USA
A Historic St Michaels Vacation
The vacation rental properties of A Historic St. Michaels Vacation are a group of five fully restored historic houses of various sizes clustered around the harbor in the histori…
Explore placePlaces To Stay, Amenities, Waterfront, Vacation Rentals | 8080 Bozman Neavitt Rd, St Michaels, MD 21663, USA
Harris Cove Cottages Bed 'N Boat
​Waterfront cottages with beautiful views and boat access.​
Explore placePlaces To Stay, Amenities, Group-ready, Pool, Waterfront, Vacation Rentals, Plan, Event Spaces | 6670 Cedar Cove Rd, Royal Oak, MD 21662, USA
Moofy's Farmhouse
Moofy's Farmhouse is located on one of the Eastern shore's most coveted waterfront parcels, providing a perfect mix of seclusion and access. Enjoy the quiet sounds of natu…
Explore placeAmenities, Pool, Places To Stay, Waterfront, Vacation Rentals | 6601 Bozman Neavitt Rd, Bozman, MD 21612, USA
Grandview at Pleasure Point
​1,300 feet of waterfront, grand view, plus piers, pool, and row boats.​
Explore placePlaces To Stay, Pool, Waterfront, Vacation Rentals, Amenities | 6448 Partridge Ln, Royal Oak, MD 21662, USA
Tremezzo Stay
Personally owned, managed, and hosted luxury rental homes in the St. Michaels area. Named after the owner's favorite trip to Lake Como, Italy, their mission is to bring yo…
Explore placeAmenities, Vacation Rentals, Places To Stay, Waterfront, Pool | 719 Goldsborough St, Easton, MD 21601, USA
Eastern Shore Vacation Rentals
Rental service offering fine vacation homes on the Eastern Shore.
Explore placeVacation Rentals, Places To Stay | 716 Long Ln, St Michaels, MD 21663, USA
Long Lane Lodge
Located in the historic neighborhood of St. Michaels, this home is yards from the Miles River and St Michaels harbor inlets. Craft breweries, wineries, restaurants, shops, and m…
Explore placePoint of Interest, Establishment, Places To Stay, Vacation Rentals, Inns And Hotels, Bed & Breakfasts | 203 Cherry St, St Michaels, MD 21663, USA
The Snuggery Inn & Suites
​Experience elegance in the heart of historic Saint Michaels, Maryland, where a unique blend of luxury, adventure, and cultural immersion come together in a picturesque set…
Explore placeVacation Rentals, Places To Stay, Waterfront, Pet-friendly | Ferry Bridge Rd, Easton, MD 21601, USA
Ferry Bridge House
A unique waterfront getaway on a private peninsula.
Explore placePlaces To Stay, Vacation Rentals | 938 Calvert Ave, St Michaels, MD 21663, USA
Nauti Hideaway
Chalet-Style Home Nestled In A Wooded SurroundingThe house is a short walk to historic downtown St. Michaels & 2 blocks from the peaceful Miles River. St. Michaels is a hist…
Explore placePlaces To Stay, Pet-friendly, Vacation Rentals, Amenities | 7634 Wales Ln, St Michaels, MD 21663, USA
Wales Family Cabin
Wales Family Cabin is a thoughtfully designed, spacious log cabin offering a peaceful nature escape just minutes from historic downtown St. Michaels. Set beside a freshwater pon…
Explore placePlaces To Stay, Inns And Hotels, Vacation Rentals | 203 Cherry St, St Michaels, MD 21663, USA
Snuggery Inn & Suites
Experience elegance in the heart of historic Saint Michaels, Maryland, where a unique blend of luxury, adventure, and cultural immersion come together in a picturesque setting.
Explore placePlaces To Stay, Vacation Rentals | 203 S Morris St, Oxford, MD 21654, USA
Oxford Market Room Rental
Our space is a cozy Oxford getaway. The studio apartment comes equipped with a full kitchen, king-sized​ bed, full size sleeper sofa and a rollaway cot. Great for small family o…
Explore placePlaces To Stay, Amenities, Group-ready, Pet-friendly, Pool, Waterfront, Vacation Rentals | 6909 Thorneton Rd, Easton, MD 21601, USA
Thorneton Point Estate
Nestled on its own private peninsula in the picturesque region of Easton, Maryland, Thorneton Point Estate offers a perfect blend of seclusion and convenience, making it an idea…
Explore placePlaces To Stay, Amenities, Group-ready, Pet-friendly, Pool, Waterfront, Vacation Rentals | 5855 Elston Shore Rd, Neavitt, MD 21652, USA
Durham-Hythe Estate
Originally built in 1942 on the scenic grounds of a former corn farm, Durham-Hythe Estate is a remarkable haven that reflects the beauty and history of Maryland’s Eastern Shore….
Explore placePlaces To Stay, Vacation Rentals | St Michaels, MD 21663, USA
Two Swan Cottages
The Two Swan Cottages are historic restored waterman's cottages located in the heart of historic St. Michaels, on Carpenter Street, only one half block from the harborfront. The…
Explore placePlaces To Stay, Amenities, Waterfront, Vacation Rentals | Tilghman, Tilghman Island, MD, USA
Tilghman Landing
Located on the Chesapeake Bay side of Tilghman Island, this beautiful property is host to several cottages that are available for rent throughout the year. The cottages have stu…
Explore placePlaces To Stay, Amenities, Pool, Waterfront, Pet-friendly, Vacation Rentals | St Michaels, MD 21663, USA
VIP Vacation Rentals
Find your perfect vacation rental through VIP Properties.
Explore placeAmenities, Vacation Rentals, Places To Stay, Plan, Event Spaces, Group-ready, Pet-friendly, Pool, Waterfront | St Michaels, MD 21663, USA
Tidewater Vacations
Offering an inventory of waterfront and stylish vacation rental homes.
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