Home Vacation Rentals By Owner In Saint Michaels, MD

Showing 51 Of 51 Vacation Rentals
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Exceptional(60)

$1056.33

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Private Vacation Home

Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels

Saint Michaels, Maryland, United States

The Two Oysters House finished renovations in 2025, featuring spectacular views from almost every room, a large private pool 18x 26ft (salt water), and a dock. The location is a couple of miles from the center of St. Michaels (Museum and Inn at Perry Cabin)- close enough to bike into town and just far enough for privacy. Bikes, kayaks, fresh linen, and bath towels are included in the rental rate. brbr***Weekly rentals are preferred in the summer. (July and August) br 3nt.min stay sleeps 8. Talbot County license ST-797-HOP 2019brbrThinking vacation should be watching sailboats from the pool, kayaking to a nearby island with a sand beach, biking into town for ice cream, or napping on the hammock. Boating options and sunset cruises are available in the town of St. Michaels May-Oct. brbrThe Two Oysters house is a short bike ride to the museum/lighthouse, restaurant, quaint shops, ice-cream parlors, cafes, bistros, brewery, and winery. You're welcome to use bikes and kayaks at the house (4-6 adult bikes 2-3 kid bikes, 4 adult kayaks and 2 kid water kayak) or feel free to bring yours. brbrThe house is on 6 acres of wooded retreat located right on the Chesapeake Bay (San Domingo Creek) with a new private pool (18x36 ft) with a spa. Spa heating options may be available with an additional utility fee. Please ask before booking. The pool/spa opens in May and closes in September.brbrThe house layout makes you feel like you are outdoors in almost every room overlooking the water and beautiful tall pine trees. View of amazing sunrise from house and dock every morning. 2 master bedrooms with private baths. 4 bedroom total (3 full bathrooms). Separate additional den/tv room. br brWhether lounging by the pool overlooking the bay, crabbing on the dock, kayaking, biking, or exploring the 6 acres of woods, there is something for everyone of all ages. brbrNo parties, weddings, rehearsal dinners, receptions, banquets, corporate retreats, or similar activities are allowed at the house. brbrKeywords: St. Michaels, waterfront, house, cottage, bay, pool, spa, dock, hot tub, bike, kayak, boat, fish, crab, in-ground pool,brFor security purposes, the owners will never ask you to make any payments via wire transfer. Beware of any response seeking payment via wire transfer.
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Bath 3

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Sleep 8

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Exceptional(138)

$810.34

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Private Vacation Home

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

Saint Michaels, Maryland, United States

The historic yet fully updated Thomas Harrison House is the premier vacation rental home in St. Michaels and has been rented as such since 1992. It is the only large vacation rental in the Town. The 18th century house (built while George Washington was President) is located on the harbor and the town park in the center of St. Michaels. The house has beautiful water views and is situated within walking distance of all museums, shops (including grocery stores and drug stores), restaurants, farmer's market, town pool, tennis courts, library, and other attractions. Rates vary by season, and whether stay is weeknight or weekend. Stays of a week or longer are discounted, as are last minute bookings.brbrA perfect location for family, families, or a group of friends vacationing, or attending weddings, reunions, or other events in St. Michaels and its surrounding areas.brbrBuilt around 1795 by Thomas Harrison Jr., 'house carpenter,' the two-story side hall/parlor clapboard house is the oldest two story dwelling in St. Michaels. It stands prominently on the town harbor adjacent the town PARK. The house is fitted with late eighteenth century style woodwork. The floors are wide plank heart of pine, and the windows have very old glass. The federal style stair, the raised six panel doors, and the period chair rails are original features. brThe house is furnished with antique and reproduction furniture in keeping with the historic nature of the house.br brA floor plan is available upon request.brbrOn the first floor of the original or 'Harrison House' are the side hall (foyer) and a large PARLOR (living room) with plenty of seating and a spectacular view of St. Michaels Harbor. To the rear of the living room is the LIBRARY having a fireplace, books, a television, stereo, games, cards and puzzles, and the DINING ROOM which can comfortably seat ten. To the rear of the dining room is a one story wing which houses a large, fully equipped KITCHEN. Also on the first floor is a DEN having a queen sleep sofa, a fireplace and a half bath. brbrFor relaxing outside on the property, the house offers a brick PATIO facing the harbor and the Miles River, and a covered PORCH facing the white picket fence enclosed back yard and gardens. br brThe second floor of the Harrison house includes the MASTER BEDROOM having a queen size poster bed and a twin trundle bed, a full bath, and an adjacent small sitting or READING ROOM which has a twin sofa bed. The second story of the rear portion of the house includes the BLUE ROOM having a queen bed, an adjacent 7X7 room with a twin bed, a full bath, and the 8X8 PEACH ROOM having a twin bed. Up a private spiral staircase from the DEN is the 15X11 WING BEDROOM with dormer windows, having a full size converted (mattress and box spring) rope bed and a full bath. brbrThe third floor of the Harrison House is the ATTIC having two rooms including one full bed. brbrThere are water views from almost every room of the house. brbrAlso available for rent are four early 19th century two bedroom fully restored cottages located within one block of the the Thomas Harrison House. brbrSeasonal, week and weekend rentals available all year-round.brbrKeywords: House
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Exceptional(148)

$409.2

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Cottage

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Saint Michaels, Maryland, United States

The truly special and recently restored historic Thomas Blades House is centrally located in the Historic District of St. Michaels, a few steps from the Town Park with magnificent waterviews. It is a 2 bedroom, 1.5 bathroom vacation cottage. Rates vary by season, and whether stay is weeknight or weekend. Stays of a week or longer are discounted, as are last minute bookings.brbrMuseums, shops (including grocery stores and a drug store), restaurants, churches, parks, tennis courts, Town pool. library, the weekly farmer's market, and other attractions are within walking distance of the house! brbrThe house is very comfortable and beautifully decorated with period and reproduction furniture. Perfectly suited for a small family or one or two couples. The house is also an ideal romantic getaway for a couple. The large family room and big back porch create an ideal environment for relaxing!brbrThe house was built around 1850 by Thomas Blades, a young sailor. brbrThe first floor of the original portion of the Blades House includes a LIVING ROOM and a DINING ROOM. To the rear of the original house on the first floor is a KITCHEN area connected to a large wood paneled FAMILY ROOM. There is a half bath off of the family room.The rear of the family room opens up by French doors to a large outdoor PORCH with ceiling fan and dining area. There is a deck to the rear of the porch for outdoor grilling.brbrThe second floor of the original portion of the Blades house includes a large BEDROOM with a queen size bed and an antique child's bed (cot size). The second floor to the rear of the house contains the large MASTER BEDROOM with a king size bed. Off of a hall between the two bedrooms is the master bathroom.brbrAn additional cottage and large waterfront house are also available for rent. brbrbrKeywords: Cottage
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Sleep 5

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Exceptional(33)

$325.77

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Apartment

Downtown St. Michaels Studio – Walk to Waterfront, Dining & Shops

Saint Michaels, Maryland, United States

Summary:brbrStay steps from Saint Michaels’ best shops, dining, and waterfront views! This stylish studio blends historic charm with modern comfort—perfect for a romantic getaway or solo escape.brbrbrbrThe Space:brbrEnjoy the charm and convenience of staying in the heart of downtown St. Michaels. This well-appointed studio is within walking distance to the waterfront, restaurants, shops, coffee shops, and local attractions, making it the perfect home base for a weekend getaway, wedding weekend, or mid-week escape.brbrbrbrThe studio is thoughtfully designed to provide everything you need for a comfortable and easy stay, all in one of the most desirable locations in town. Many guests arrive, park their car, and walk everywhere for the rest of their stay.brbrbrbrOne of the best features of this property is the location. You are within walking distance to:brbr- The St. Michaels waterfrontbrbr- Restaurants and barsbrbr- Coffee shopsbrbr- Boutique shoppingbrbr-The Chesapeake Bay Maritime Museumbrbr- Local wedding venuesbrbr- Seasonal festivals and eventsbrbrbrbrThis is a great option for guests attending weddings, visiting for a weekend getaway, or looking for a relaxing few days on the Eastern Shore.brbrbrbrCurated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your hosts.brbrbrbrGuest Access:brbrThis property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.brbrbrbrThe Neighborhood:brbrYou’re truly in the center of it all—quaint boutiques, delicious seafood spots, harbor strolls, and live music venues are just steps away. St. Michaels’ rich history and vibrant culture are yours to explore.brbrbrbrGetting Around:brbrWalk everywhere in town, or rent a bike for a scenic ride. Free private parking makes exploring the Eastern Shore a breeze.
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Exceptional(7)

$1378.15

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Country House

LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL, DOCK, GOURMET KITCHEN

Saint Michaels, Maryland, United States

Come slip away and enjoy Perry Point—a custom built nautical farmhouse that provides the best combination of luxury accommodations, an ideal location, and spectacular views from every room. Highlights are the 150+-year-old random width oak floors, chef's kitchen, gas fireplace, steam room and jacuzzi, oversized screen porch, a second floor great room with shuffleboard, and a large second floor porch. Outside you'll find a heated pool, custom outdoor pizza oven, dock, fire pit, kayaks, paddle board, two bikes and two hammocks to enjoy the amazing views of the wraparound coves of Porters Creek and the Miles River. The historic two acre elevated and professionally landscaped property provides plenty of room for bocce, croquet, and badminton. A nature oasis, Perry Point is the perfect place to observe migrating birds, resident eagles, osprey, blue herons, and turtles. Catch crabs from the pier and fish from the dock. One mile from downtown Saint Michaels, Perry Point is an easy bike or boat ride away from Saint Michael's harbor. This perfect river retreat is waiting for you!brbrbrDisclosure: per county regulations there is a standard lease agreement that will be sent following the acceptance of your booking.brProp ID:2793465brSTRN-22-40
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Bath 4

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Sleep 6

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Exceptional(22)

$924.91

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Private Vacation Home

Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!

Saint Michaels, Maryland, United States

Talbot County MD License #STN-24-6brbrWater front home nestled in quaint village of Bozman with dock/pier for fishing, crabbing or just enjoying what the Eastern Shore has to offer - sipping your beverage of choice from the deck just off the gathering room where there is a fireplace and comfy seating and shelves of games and more. The breakfast nook, counter seating and large custom kitchen make cooking meals a delight . A second space where adults can watch their shows or read a good book is tucked off the foyer as well as the large dining room with seating for all. We have included a child size table for two , AS WELL. All on the first floor. The second floor sleeps EIGHT very comfortably in bedroom with day bed w/trundle and its two king bedrooms and one bedroom with two double size beds, one in suite bathroom and one hall bathroom. Don't forget the breezy covered front porch reminding you of days gone by.brAll this just a short drive to St. Michaels for shopping and museums or Tilghman Island and a glimpse of the mighty Chesapeake Bay and a look at life in a fisherman's village.brbr24 AMP DEDICATED CAR CHARGER EQUIPPED FOR TESLA
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Sleep 8

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Exceptional(1)

$315.09

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Bed & Breakfast

The Snuggery Inn & Suites Sea Grass Room

Saint Michaels, Maryland, United States

This stylish place is within steps of all the shopping, dining, nightlife and museums. The Snuggery Inn & Suites offers a unique blend of luxury, adventure, and cultural immersion in a picturesque setting. Though meals are not provided; upon your arrival you`ll find that your mini refrigerator is stocked with breakfast parfaits, OJ, bottled water and creamer for the coffee maker. For the safety and comfort of our residents with severe allergies, no pets of any kind are permitted on the premises.brbrbrbrThe Sea Grass Room is a second floor room with a queen bed and private en suite bathroom. The room includes use of the West Parlor. This is the parlor that all guests enter into when they walk through the front door. brbrHowever, it is the seating area intended only for the Sea Grass guests and the innkeeper. There is only one other guest room in this part of the property and those guests have their own parlor.
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Exceptional(2)

$446.24

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Bed & Breakfast

The Snuggery Inn & Suites Captain`s Quarters

Saint Michaels, Maryland, United States

This stylish place is within steps of all the shopping, dining, nightlife and museums. The Snuggery Inn & Suites offers a unique blend of luxury, adventure, and cultural immersion in a picturesque setting. Though meals are not provided; upon your arrival you`ll find that your mini refrigerator is stocked with breakfast parfaits, oj, bottled water and creamer for the coffee maker. For the safety and comfort of our residents with severe allergies, no pets of any kind are permitted on the premises.
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Exceptional(4)

$790.88

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Apartment

Downtown St. Michaels | Porch + Pet-Friendly

Saint Michaels, Maryland, United States

Summary:brStay in the heart of St. Michaels at this stylish 3-bedroom retreat, just steps from boutique shops, waterfront dining, and historic charm. Relax on the private porch, enjoy a spacious open layout, and bring your pup along — dogs are welcome here! Whether it’s a romantic getaway, friends’ weekend, or family trip, this walkable downtown escape blends modern comfort with small-town charm for an unforgettable stay on Maryland’s Eastern Shore.brbrThe Space:brWelcome to your St. Michaels getaway, a thoughtfully designed 3-bedroom apartment where comfort meets convenience. Situated right in the heart of downtown, this retreat allows you to park once and explore everything on foot. Inside, you’ll find a bright, open-concept living room with cozy seating and abundant natural light, a fully equipped kitchen with modern appliances and all the essentials for cooking or entertaining, and three spacious bedrooms featuring plush bedding and carefully curated décor for restful nights. The full bathroom is stocked with fresh towels, and the private porch offers the perfect spot for morning coffee or unwinding with a glass of wine after dinner in town. Whether visiting for a long weekend or an extended stay, this apartment is designed to feel like home while giving you the best of downtown living.brbrWhat you'll bring:br- Walk to waterfront restaurants, boutique shops, and historic attractions.br- Dog-friendly (with pet fee) — bring your pup along!br- Private porch for coffee or cocktails,br- Central downtown location, yet peaceful and welcoming.br- Stylish interiors with modern comfort.brbrCurated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your hosts.brbrGuest Access:brThis property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.brbrThe Neighborhood:brSt. Michaels is known for its charming harbor, local wineries, sailing excursions, and boutique shopping. From this home, you’re just steps away from the best restaurants, galleries, and waterfront spots. Spend the day exploring town, book a boat tour, or simply relax on the porch and enjoy the small-town vibe.brbrGetting Around:brWalk everywhere in town, or rent a bike for a scenic ride. Free private parking makes exploring the Eastern Shore a breeze.brbrOther Things to Note:brThere is stairs to enter the apartment. We offer a starter supply of toilet paper and paper towel, we recommend bringing more for longer stays. We can welcome your furry friend for a nonrefundable pet fee of $200.
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Exceptional(150)

$920.43

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Cottage

St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3

Saint Michaels, Maryland, United States

brAs Saint Michael's Premier STR, we take this title very seriously, so read on to see what we've done this off season. Harbor Hideaway's in town location is just steps away from everything that St. Michael's has to offer. We've added a pool with a heater for guest stays in the spring and fall. The pool is quite large and the heater does help bring the water to around 80 degrees, but it can still feel cool is the temps are chilly. *Please understand before you book, the pool is only for our reserved guests staying at the cottage and never for pets. brThe 1.5 story cottage was built in the 1940's. It was completely torn apart and remodeled in the the 90's. HH has been lucky with its owners. When owners actually use their property, (vs just as a rental investment) they care about it, and care FOR it. HH has been continually updated. Our current owners have beautiful designer taste, I call it Serena and Lily coastal....which makes it feel so good to spend time there. Our reviews often speak of our comfort and cleanliness, this remains a top priority for us. Again, this season, I fully expect many of our guests will speak of their love for the new coastal look! If you haven't seen our continued changes, it's time you booked! HH could be a photo shoot for S&L furnishings, it's that beautiful! brThe off-season is always used to continue updates to HH. Besides the smaller things like new paint in and out; new windows, ceiling fans, and headboards in the bedrooms, mattresses, the bathrooms got a great new fabulous changes and the kitchen! A chef driven design with a stove you'll want to take home with you. New tile floors that look like whitewashed, patterned wood, new cabinets. We will continue to help you get the sleep that every getaway should offer with our new deluxe mattresses made up with resort quality, freshly pressed linens. We think you'll find this beautiful new look of the interior, in addition to the pool and patio, will make your stay feel like you just spent time at a high end resort. We hope all the updates please you, make you smile as you see them, and that they will make you want to come back time after time. brHarbor Hideaway is perfect for 1 to 2 couples, a girls' wknd, a small family, or anyone just in need of a relaxing getaway. HH is also set up for remote work with high speed internet for those looking for a multi-tasking getaway. Our guests have the best of the Eastern Shore living, with restaurants and shops in Saint Michaels, fresh crab from local watermen, delightful boat tours and skipjack rides, the nearby Chesapeake Bay Maritime Museum and abundant history and charm all around- all while staying in a quaint residential neighborhood.brHH guests also enjoy:brKayaking through the harbor and out onto the Miles River or San Domingo Creek and following one of several kayaking pathways ( 2 boat ramps are near the cottage and available for easy entry) * HH has two kayaks for guest use. 1 single and 1 tandem plus life jackets.brbrTaking a ride about town on one of the 4 provided bikes.brBrowse the Bookhound for your next read!brTossing a game of cornholebrWatching the crab boats harvest the Bay's bountybrTaking a well-deserved nap on one of the two queen beds with new and comfy mattresses.brEnjoying one of the many in-town restaurants, or cook in HH's well-equipped kitchen or outdoor charcoal grill. When you don't want to cook- Simpatico now offers delicious meals to go.brCracking crabs at one of the any restaurants or bringing them home to enjoy.brTaking an evening walk and stopping for ice cream.brEnding your evening by the firepit making s'mores.brSipping coffee or cocktails poolside or on a rocker on the front porch while people watching.brTrying a craft beer and locally made spirits at the top of the street.brGoing wine tasting a few blocks away- The Mill near Gina's (delicious margarita's)brIndulging in a cigar at the Old Mill (2 min walk)brPicking up nautical antiques and luxe home decor.brIndulging in a spa treatment (or two)brTry drinks at Fool's LanternbrEastern Shore Brewery - The Gallerybr208 Talbot- new management in 2024brRuse. Corah's Corner for seafood brSimpaticobrLemoncello
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Exceptional(14)

$658.97

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Private Vacation Home

Grace Cottage, Saint Michaels Walk to everything!

Saint Michaels, Maryland, United States

This property is under new ownership. Please go to https://Vrbo.com/5093945/ to book your stay at Grace Cottage. If you have a current reservation ..don't worry! You are still booked. I'll be reaching out to have your rebooked on new link. Thank you! Michelle
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Home Most popular vacation rentals in Saint Michaels

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Exceptional(14)

$315.09

/ Nightly
Bed & breakfast

The Snuggery Inn & Suites Sea Grass Room

Saint Michaels, Maryland, United States

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Sleep 2

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Exceptional(14)

$468.41

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Private vacation home

Downtown Retreat with Bikes, Fire Pit & Kayaks

Saint Michaels, Maryland, United States

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Sleep 4

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Exceptional(14)

$446.24

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Bed & breakfast

The Snuggery Inn & Suites Captain`s Quarters

Saint Michaels, Maryland, United States

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Sleep 2

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Exceptional(14)

$402.60

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Private vacation home

Walk to Everything House

Saint Michaels, Maryland, United States

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Sleep 6

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Exceptional(14)

$371.33

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Cottage

Cottage #8 Herons Nest Lg 2 rooms Under Main House

Saint Michaels, Maryland, United States

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Sleep 6

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Exceptional(14)

$325.77

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Downtown St. Michaels Studio – Walk to Waterfront, Dining & Shops

Saint Michaels, Maryland, United States

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Exceptional(14)

$294.33

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Cottage

#2 Egret Cottage Harris Cove

Saint Michaels, Maryland, United States

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Exceptional(14)

$278.10

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Private vacation home

Nice home in Polaca with private swimming pool, can be inside or outside

Polaca, Polaca, Croatia

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Exceptional(14)

$294.33

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Cottage

#3 Mallard Cottage (located 3rd down drive)

Saint Michaels, Maryland, United States

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Exceptional(14)

$1905.56

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Private vacation home

TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool

Saint Michaels, Maryland, United States

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Bath 3

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