St. Michaels Rentals
From $372 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 $372 per night (USD)VRBO
From $591 per night (USD)Expedia
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Recently renovated and newly furnished, this lovely in-town cottage is close to all the amenities and charms of historic ...
From $591 per night (USD)Expedia
From $358 per night (USD)VRBO
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
The truly special and recently restored historic Thomas Blades House is centrally located in the Historic District of St ...
From $358 per night (USD)VRBO
From $251 per night (USD)Expedia
Dollhouse in Central Historic St Michaels
- Bedrooms:
- 2
- 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 $251 per night (USD)Expedia
From $327 per night (USD)VRBO
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
The extraordinary fully restored historic John Bruff House, located on the Town park and harbor, has magnificent St. Mic ...
From $327 per night (USD)VRBO
From $294 per night (USD)Expedia
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
The recently restored historic Washington Melson House, located at 206 Locust St. is a 2 bedroom vacation cottage that i ...
From $294 per night (USD)Expedia
From $319 per night (USD)VRBO
Walk to Everything House
- Bedrooms:
- 2
- 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 $319 per night (USD)VRBO
From $384 per night (USD)Expedia
Charming 1-bedroom cottage in downtown Saint Michaels
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Stay comfortably in Saint Michaels at this 1-bedroom cottage. Nestled in a beautiful and peaceful setting, this brillian ...
From $384 per night (USD)Expedia
From $675 per night (USD)VRBO
St. Michael's Premier In-Town Rental with heated pool-opens 4\/22
- 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 $675 per night (USD)VRBO
From $462 per night (USD)VRBO
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 9
The historic yet fully updated Thomas Harrison House is the premier vacation rental home in St. Michaels and has been re ...
From $462 per night (USD)VRBO
From $318 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 $318 per night (USD)VRBO
From $537 per night (USD)Expedia
St Michaels is waiting for you. Join us at CoCo's
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: **Welcome to Coco's Nest: Your Intimate Retreat in Saint Michaels** Nestled in the charming historic district ...
From $537 per night (USD)Expedia
From $624 per night (USD)VRBO
Grace Cottage, Saint Michaels Walk to everything!
- Bedrooms:
- 3
- 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 $432 per night (USD)Expedia
Join Us In St Michaels, Book Spring\/Summer Now
- 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 $432 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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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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From $739 per night (USD)VRBO
Delightful Close to town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stay near Saint Michaels and enjoy a wonderful town and a great stay. There is lots to do and shop for in the quaint tow ...
From $739 per night (USD)VRBO
From $371 per night (USD)VRBO
The heart of St Michaels awaits.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
Summary: Nestled in the vibrant heart of the St. Michaels historic district, this stunning one-bedroom, one-and-a-half-b ...
From $371 per night (USD)VRBO
From $801 per night (USD)VRBO
Downtown St. Michaels | Bikes | Kayaks | Private Pier
- Bedrooms:
- 3
- 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 $801 per night (USD)VRBO
From $1399 per night (USD)Expedia
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
- Bedrooms:
- 5
- 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 $1399 per night (USD)Expedia
From $693 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 $693 per night (USD)VRBO
From $600 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 $600 per night (USD)Expedia
From $1416 per night (USD)VRBO
Classic Eastern Shore Waterfront Manor House - ST-936
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Quintessential Eastern Shore experience on 30 acres 1.5 miles from downtown St. Michaels. Original house dates to the e ...
From $1416 per night (USD)VRBO
From $342 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 $342 per night (USD)VRBO
From $966 per night (USD)VRBO
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 8
TREMEZZO STAY - SPENCER CREEK CABIN Our properties are owned, managed, and hosted by us. We deliver personally hosted ...
From $966 per night (USD)VRBO
From $1316 per night (USD)VRBO
ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FANTASTIC LOCATION- ONLY A MILE TO THE TOWN OF ST MICHAELS. The Harbor Shuttle can even pick you up from your private d ...
From $1316 per night (USD)VRBO
From $811 per night (USD)VRBO
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Eastern Shore Vacation Rentals presents Crew's Quarters. Step into this idyllic, uniquely Eastern Shore Nanticoke mid- c ...
From $811 per night (USD)VRBO
From $689 per night (USD)VRBO
An Afternoon Nap in the Hammock is a Must.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: This beautiful home is minutes from historic St Michaels. Enjoy your morning coffee on the covered deck. Days c ...
From $689 per night (USD)VRBO
From $1458 per night (USD)VRBO
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
The impressive 6BR, 5.5BA St. Michaels waterfront getaway has recently been remodeled throughout with your comfort in mi ...
From $1458 per night (USD)VRBO
From $1472 per night (USD)Expedia
Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Licensed by Talbot Co MD STRN-23-11. Mimimum 7 night reservations only - Sat to Sat. Our property is ideally suited for ...
From $1472 per night (USD)Expedia
From $451 per night (USD)VRBO
Charming Stay, Just Minutes from Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: A stylish home that has all one needs for a fabulous getaway. Our quaint town has a bustling main street filled ...
From $451 per night (USD)VRBO
From $480 per night (USD)VRBO
Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet Friendly. A VIP Vacation Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
License # STN-23-39...(3 night minimum off season.) A long, driveway on two, private acres, leads to this updated and ch ...
From $480 per night (USD)VRBO
From $281 per night (USD)VRBO
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 $281 per night (USD)VRBO
From $774 per night (USD)VRBO
2025 Renovation Beautiful Waterfront Home w\/ Pool In St. Michaels
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful house with spectacular views from almost every room. Private large pool (salt water) and dock. Location is a c ...
From $774 per night (USD)VRBO
From $1268 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 $1268 per night (USD)VRBO