St. Michaels Rentals
From $374 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 $374 per night (USD)VRBO
From $413 per night (USD)Expedia
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 $413 per night (USD)Expedia
From $971 per night (USD)VRBO
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 $971 per night (USD)VRBO
From $329 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 $329 per night (USD)Expedia
From $374 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 $374 per night (USD)VRBO
From $329 per night (USD)Expedia
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 $329 per night (USD)Expedia
From $361 per night (USD)VRBO
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 $361 per night (USD)VRBO
From $747 per night (USD)Expedia
Grace Cottage, St Michaels Walk to everything!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Grace Street Cottage, a charming retreat in the heart of the historic district of St. Michaels. Grace Cottag ...
From $747 per night (USD)Expedia
From $488 per night (USD)VRBO
Downtown Flat • Walk to Dining & Shops • Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This 1-bedroom home is jam-packed with amenities & has EVERYTHING you need for an amazing vacation in St. Mich ...
From $488 per night (USD)VRBO
From $563 per night (USD)Expedia
Downtown St. Michaels | Porch + Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Stay in the heart of downtown St. Michaels in this charming, professionally managed studio apartment, perfectl ...
From $563 per night (USD)Expedia
From $516 per night (USD)VRBO
St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27
- 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 $516 per night (USD)VRBO
From $741 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 $741 per night (USD)VRBO
From $382 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 $382 per night (USD)VRBO
From $694 per night (USD)Expedia
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. Pe ...
From $694 per night (USD)Expedia
From $239 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 $239 per night (USD)VRBO
From $321 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 $321 per night (USD)Expedia
From $372 per night (USD)VRBO
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 ...
From $372 per night (USD)VRBO
From $975 per night (USD)Expedia
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 ...
From $975 per night (USD)Expedia
From $630 per night (USD)VRBO
Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover your home away from home in the heart of historic St. Michaels. Located on a peaceful residential street, this ...
From $630 per night (USD)VRBO
From $937 per night (USD)Expedia
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
1/2 Mile to Historic District, Pickleball Court, 3 Private Suites! Step into this idyllic, uniquely Eastern Shore Nanti ...
From $937 per night (USD)Expedia
From $1297 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 $1297 per night (USD)VRBO
From $1567 per night (USD)Expedia
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
No expense spared! The impressive 6BR, 5.5BA St. Michaels waterfront getaway has recently been remodeled throughout wit ...
From $1567 per night (USD)Expedia
From $582 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 thoughtfu ...
From $582 per night (USD)VRBO