St. Michaels Rentals
From $765 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 $765 per night (USD)VRBO
From $327 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 $327 per night (USD)VRBO
From $631 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 $631 per night (USD)VRBO
From $311 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 $311 per night (USD)VRBO
From $360 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 $360 per night (USD)VRBO
From $754 per night (USD)VRBO
Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The Two Oysters House finished renovations in 2025, featuring spectacular views from almost every room, a large private ...
From $754 per night (USD)VRBO
From $407 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 $407 per night (USD)VRBO
From $1550 per night (USD)Expedia
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Fantastic Family Compound Just 1/2 Mile to Historic District! Located just on the outskirts of St. Michaels, this fanta ...
From $1550 per night (USD)Expedia
From $687 per night (USD)VRBO
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Charming Waterfront Cottage Within Minutes to Historic St. Michaels. Kayaks and Bikes Included! Comfortably furnished an ...
From $687 per night (USD)VRBO
From $1279 per night (USD)VRBO
LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Come slip away and enjoy Perry Point—a custom built nautical farmhouse that provides the best combination of luxury acco ...
From $1279 per night (USD)VRBO
From $295 per night (USD)VRBO
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)VRBO
From $757 per night (USD)Expedia
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 $757 per night (USD)Expedia
From $359 per night (USD)VRBO
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)VRBO
From $294 per night (USD)Expedia
Modern Flat in the Heart of St. Michaels – Walk Everywhere
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Welcome to Flat 207, your private retreat in the heart of beautiful St. Michaels. Located just steps from the h ...
From $294 per night (USD)Expedia
From $304 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 $304 per night (USD)VRBO
From $353 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 $353 per night (USD)Expedia
From $296 per night (USD)VRBO
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 $296 per night (USD)VRBO
From $1002 per night (USD)VRBO
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
TREMEZZO STAY - SPENCER CREEK CABIN Our properties are owned, managed, and hosted by us. We deliver personally hosted ...
From $1002 per night (USD)VRBO
From $258 per night (USD)VRBO
Harbor View Suite\nTalbot County License Number STRN-25-58
- 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 $258 per night (USD)VRBO
From $1355 per night (USD)VRBO
ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
YOUR CHESAPEAKE DREAM GETAWAY-SPECIAL NIGHTLY RATE OF $950 FOR BOOKINGS MAY 26-30,JULY 16-19 and JULY 27-8/2 Fantastic ...
From $1355 per night (USD)VRBO
From $284 per night (USD)VRBO
Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Stay steps from Saint Michaels’ best shops, dining, and waterfront views! This stylish studio blends historic c ...
From $284 per night (USD)VRBO
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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 ...
Click For PricingExpedia
From $605 per night (USD)VRBO
St. Michaels Escape | Pool, Hot Tub & Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to The Kipsy, your private waterfront oasis on Porters Creek, just minutes from charming St. Michaels. ...
From $605 per night (USD)VRBO
From $389 per night (USD)VRBO
Downtown Retreat with Bikes, Fire Pit & Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Just minutes from downtown St. Michaels, this stylish 2-bedroom retreat combines modern design with thoughtful ...
From $389 per night (USD)VRBO
From $517 per night (USD)VRBO
Very cosy and nicely appointed Waterfront Cottage with gorgeous views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
License # STRN-24-69...A long, driveway leads to this updated and charming 1930's St. Michaels Cottage situated on two a ...
From $517 per night (USD)VRBO
From $480 per night (USD)Expedia
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)Expedia
From $499 per night (USD)VRBO
Elegant 2-Bedroom Retreat in Historic Saint Michaels – Walk to Dining & Shops
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to Coco’s Nest, your intimate escape in the charming historic district of Saint Michaels, Maryland. Per ...
From $499 per night (USD)VRBO
From $336 per night (USD)Expedia
3 Bedroom St. Michaels Retreat | 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 $336 per night (USD)Expedia
From $331 per night (USD)VRBO
The Snuggery Inn & Suites Sea Grass Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This stylish place is within steps of all the shopping, dining, nightlife and museums. The Snuggery Inn & Suites offers ...
From $331 per night (USD)VRBO
From $446 per night (USD)Expedia
The Snuggery Inn & Suites Captain`s Quarters
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This stylish place is within steps of all the shopping, dining, nightlife and museums. The Snuggery Inn & Suites offers ...
From $446 per night (USD)Expedia
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Downtown St. Michaels | Porch + Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Stay in the heart of St. Michaels at this stylish 3-bedroom retreat, just steps from boutique shops, waterfront ...
Click For PricingVRBO