124+ Private Villas and Holiday Rentals in St. Michaels |
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St. Michaels Holiday Rentals

About Casai's Private Villas and Holiday Rentals in St. Michaels

Discover more than 124 vacation rentals available in St. Michaels. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in St. Michaels.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in St. Michaels, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near St. Michaels. On average, places to stay near St. Michaels offer 1193.13 ft², with nightly prices averaging US $687.

With Casai, finding and comparing holiday rentals in St. Michaels is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in St. Michaels

Type Count
Vacation Homes 76
Cottages 22
Holiday Apartments 7
Villas 1

Use these Quick Filters to Find a Holiday Rental in St. Michaels

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in St. Michaels.

Weather in St. Michaels, MD

View the weather forecast for St. Michaels before booking your St. Michaels Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around St. Michaels, MD

Casai offers a large selection of top attractions around St. Michaels . Research things to do on your vacation before you visit St. Michaels.


St. Michaels Winery
Chesapeake Bay Maritime Museum
St. Michaels Museum
U.S. Naval Academy
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Chesapeake Beach Water Park
Anne Arundel Medical Center
Maryland State House
Navy-Marine Corps Memorial Stadium
Rod n Reel Charter Fishing
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
Queenstown Premium Outlets
Annapolis Maritime Museum
Great Marsh Park
Harriet Tubman Museum and Educational Center
Oxford Museum

Other Places to Stay in St. Michaels, MD


Claiborne 124 Properties
St. Michaels Winery 92 Properties
Bozman 90 Properties
St. Michaels Museum 90 Properties
Rio Vista 88 Properties
Chesapeake Bay Maritime Museum 87 Properties

Frequently Asked Questions About St. Michaels?

What are the top holiday rentals in St. Michaels?

With numerous options available in St. Michaels, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in St. Michaels:

How many holiday rentals have private pools in St. Michaels?

Discover a selection of holiday rentals with private pools near St. Michaels with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in St. Michaels are best for families?

If you're searching for a family-friendly holiday home in St. Michaels, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in St. Michaels:

How many Casai.com holiday rentals are available in St. Michaels?

As of 2025, Casai boasts over 124 properties listed in the St. Michaels area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in St. Michaels.

Nearby Neighborhood (1) 
Neighborhood Property Count
Rio Vista Vacation Rentals in St. Michaels, Maryland 88

People Also Ask

There are 124 St. Michaels, MD Holiday Rentals

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