Eastern Shore Land Conservancy - Canton Farm Conservation Reserve Enhancement Program Easement Rentals
From $415 per night (USD)VRBO
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The recently renovated Carpenter St. Cottage is centrally located in village of St. Michaels. The house is a 2 bedroom 2 ...
From $415 per night (USD)VRBO
From $677 per night (USD)Expedia
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cottage in Center of Historic St. Michaels This lovely in-town cottage is close to all the amenities and charms of hist ...
From $677 per night (USD)Expedia
From $1751 per night (USD)VRBO
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County STR License #ST-102-WEI Located just on the outskirts of St. Michaels, this fantastic family vacation com ...
From $1751 per night (USD)VRBO
From $1026 per night (USD)Expedia
Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 9
Eastern Shore Vacation Rentals presents The Water House. Beautifully appointed with artwork and antiques, The Water Hous ...
From $1026 per night (USD)Expedia
From $691 per night (USD)VRBO
Minutes from Downtown St. Michaels | Private Dock | Kayaks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Easy, One-Level Living Let go of your cares and enjoy the respite of this Covey Creek waterfront home. Let the kids play ...
From $691 per night (USD)VRBO
From $295 per night (USD)Expedia
Dollhouse in Central Historic St Michaels
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Dollhouse is a fully updated two story centrally located 1870s historic house with 2 bedrooms and 1.5 baths. The ho ...
From $295 per night (USD)Expedia
From $761 per night (USD)VRBO
Downtown St. Michaels | Bikes | Kayaks | Private Pier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming Waterfront Cottage in St Michaels Begin your day at Riverview Retreat with a beautiful sunrise and be amazed wi ...
From $761 per night (USD)VRBO
From $359 per night (USD)Expedia
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The extraordinary fully restored historic John Bruff House, located on the Town park and harbor, has magnificent St. Mic ...
From $359 per night (USD)Expedia
From $331 per night (USD)VRBO
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The recently restored historic Washington Melson House, located at 206 Locust St. is a 2 bedroom vacation cottage that i ...
From $331 per night (USD)VRBO
From $358 per night (USD)Expedia
Walk to Everything House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The historic house which was restored from 2016-2020, is conveniently located on a quiet street near the Blue Crab coffe ...
From $358 per night (USD)Expedia
From $363 per night (USD)VRBO
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The truly special and recently restored historic Thomas Blades House is centrally located in the Historic District of St ...
From $363 per night (USD)VRBO
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Waterfront St Michaels Vacation Rental w/ Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Wake up on the water with a stay at this stylish 3-bedroom, 3.5-bath, St Michaels vacation rental! Relax, recharge, and ...
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From $480 per night (USD)VRBO
Bateau Cabin one of three Cove Cabins in St Michaels
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover unparalleled relaxation and tranquility at The Bateau Cabin, our beautifully designed waterfront retreat. Locat ...
From $480 per night (USD)VRBO
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Charming 1-bedroom cottage in downtown Saint Michaels
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay comfortably in Saint Michaels at this 1-bedroom cottage. Nestled in a beautiful and peaceful setting, this brillian ...
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From $772 per night (USD)VRBO
St. Michael's Premier In-Town Rental with heated pool.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
As Saint Michael's Premier STR, we take this title very seriously, so read on to see what we've done this off season. H ...
From $772 per night (USD)VRBO
From $392 per night (USD)VRBO
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Less than a mile to the town center, this property is a perfect location for those seeking a tranquil Eastern Shore esca ...
From $392 per night (USD)VRBO
From $701 per night (USD)VRBO
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 9
The historic yet fully updated Thomas Harrison House is the premier vacation rental home in St. Michaels and has been re ...
From $701 per night (USD)VRBO
From $316 per night (USD)VRBO
Stay in the HEART of Saint Michaels!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stunning and completely renovated 1940s bungalow in the heart of Saint Michaels! Located just steps from shopping, resta ...
From $316 per night (USD)VRBO
From $544 per night (USD)VRBO
Apartment in Downtown – Walk to Everything!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to Coco's Nest: Your Intimate Retreat in Saint Michaels Nestled in the charming historic district of ...
From $544 per night (USD)VRBO
From $377 per night (USD)Expedia
St. Michaels Escape – Walk to Town!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Easy walking and biking distance to the heart of St. Michaels. Enjoy shops, restaurants, and waterfront charm j ...
From $377 per night (USD)Expedia
From $857 per night (USD)VRBO
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License STN-22-27 This 4-bedroom, 1.5-bathroom waterfront getaway features a character-filled interio ...
From $857 per night (USD)VRBO
From $909 per night (USD)Expedia
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Eastern Shore Vacation Rentals presents Crew's Quarters. Step into this idyllic, uniquely Eastern Shore Nanticoke mid- c ...
From $909 per night (USD)Expedia
From $624 per night (USD)VRBO
Grace Cottage, Saint Michaels Walk to everything!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About this space Welcome to Grace Street Cottage in the heart of Saint Michaels. Walk to shops, restaurants and experien ...
From $624 per night (USD)VRBO
From $294 per night (USD)Expedia
Studio in Downtown – Walk to Everything!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Spring and Summer weekends are filling fast with guest coming to explore our fabulous little town. Welcome ...
From $294 per night (USD)Expedia
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Seasonal Rental: Artisan designed 3 bedroom home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Kick back and relax St Michaels' style in this seasonal rental. This area of St Michaels requires a 4 month minimum stay ...
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From $2969 per night (USD)Expedia
Minutes from St. Michaels | Newly Renovated | Pool | Private Dock | Kayaks | Bik
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Your Unforgettable Waterfront Retreat! Escape to the unparalleled luxury of Eventide Farm, a waterfront retreat in St. ...
From $2969 per night (USD)Expedia
From $1477 per night (USD)VRBO
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
The impressive 6BR, 5.5BA St. Michaels waterfront getaway has recently been remodeled throughout with your comfort in mi ...
From $1477 per night (USD)VRBO
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Vacation Rental in Historic St. Michaels
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right ab ...
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Spacious Family Getaway – Summer Ready!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: Pack your bags and gather the crew—this bright and welcoming 4-bedroom, 4.5-bath home is everything a summer ge ...
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From $301 per night (USD)Expedia
Cottage downtown on a quiet street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
In search of a cottage in downtown St. Michaels for a nice weekend? Located on a quiet street, yet steps away from shopp ...
From $301 per night (USD)Expedia
From $907 per night (USD)VRBO
Beautiful Large 3 Bdrm Luxury suites with outdoor pool & spa, close walk to town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County Short-Term Rental License STN-23-2 Villa estates ...
From $907 per night (USD)VRBO
From $259 per night (USD)Expedia
Harbor View Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This unique space has amazing appeal. Within walking distance of every point of interest in Saint Michaels; including th ...
From $259 per night (USD)Expedia
From $315 per night (USD)VRBO
The heart of St Michaels awaits.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Nestled in the vibrant heart of the St. Michaels historic district, this stunning one-bedroom, one-and-a-half-b ...
From $315 per night (USD)VRBO
From $923 per night (USD)VRBO
Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Two Oysters House finished renovations in 2025, featuring spectacular views from almost every room, a large private ...
From $923 per night (USD)VRBO