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St. Michaels holiday rentals

We found 207 holiday rentals — enter your dates for availability

Select from 35 homes, 10 cottages and other holiday rentals in St. Michaels to find one that's perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you expect for your stay, which might include cable TV and a washer and dryer. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Head to the historical city of St. Michaels

The area's museums and history are just some of the reasons to come on holiday to St. Michaels. Travellers to this romantic city praise the boating, seafood restaurants and shopping. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around St. Michaels

Do you want to find attractions to see while you're in town? Venture out of your holiday home and experience everything that makes St. Michaels a fun spot to go on holiday. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • St. Michaels Winery (0.4 mi / 0.6 km)
  • Queenstown Harbor Golf Links (14.3 mi / 23.1 km)
  • Queenstown Harbor Golf Club (14.4 mi / 23.1 km)
  • Chesapeake Beach Water Park (18 mi / 29 km)
  • U.S. Naval Academy Golf Club (19.4 mi / 31.2 km)
  • Easton Cycle and Sport (8.8 mi / 14.1 km)

Exploring the natural features in St. Michaels

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, St. Michaels is a great place to get out in nature. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Chesapeake Bay Environmental Center (11.2 mi / 18 km)
  • Gerry Boyle Park at Great Marsh (16 mi / 25.8 km)
  • Shadyside Park (16.2 mi / 26.1 km)
  • Long Wharf Park (16.6 mi / 26.8 km)
  • Bay Ridge Beach (16.7 mi / 26.9 km)
  • Eastern Neck National Wildlife Refuge (16.9 mi / 27.2 km)

Transport to and around St. Michaels

The nearest airport is in Easton, MD (ESN-Easton - Newnam), located 8.8 mi (14.1 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Fort Meade, MD (FME-Tipton), which is 35.5 mi (57.2 km) away.

Frequently asked questions

What is the best area to stay in St. Michaels when booking a holiday home?
Among the more in-demand neighbourhoods for a St. Michaels holiday home is Claiborne. When you lock in your holiday property, you can look forward to having the entire place to yourself. So you won’t have to share it with anybody other than your people.
What is the most popular type of holiday home accommodation in St. Michaels?
Cottages are the most popular kind of holiday home in St. Michaels, according to our data. Even if you’ve got something different in mind, Stayz has holiday homes in a variety of shapes and sizes. Filter our options to find your perfect match.
How much does it cost to rent a holiday home in St. Michaels?
Season, length of stay and property type are among the factors that can determine the price of a holiday home. Simply click on your travel dates to find your perfect fit. From cosy country cottages to expansive villas, all Stayz holiday homes provide unbeatable value.
How much does it cost to rent a beach house in St. Michaels?
When you travel and the size and style of the property will influence the cost of your beachside stay. Put in your St. Michaels travel dates to see all your options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the amenities and features you want in your beach house.
Are there pet-friendly holiday homes in St. Michaels?
You’re in luck! There are. You’ll have your pick of eight holiday homes that cater to pets in St. Michaels. Plenty of our pet-friendly holiday homes have a garden for your fur child to have fun in, complimentary treats, special dog beds and proximity to parks. Apply the “Pets allowed” filter to find a pad that’ll get tails wagging on Stayz.
Can I rent a house with a pool in St. Michaels?
Add a whole new level of fun to your adventure by staying in one of the seven houses with a private pool in St. Michaels. Use our handy search filter to find the kind of property you want on Stayz, and then spend leisurely days splishing and splashing in a swimming pool that’s all your own.
What are popular home amenities in St. Michaels?
A fireplace, a nearby waterfront and a swimming pool are rated the most popular home amenities in St. Michaels. Whether you’re travelling as a party of one, with your significant other or as a family group, Stayz will help you find a holiday home that fits your style with all the conveniences you’re looking for.
Are there large group holiday homes in St. Michaels?
With five St. Michaels holiday homes that can accommodate five or more people, you can invite a few extra family members or buddies along. Whether you’re planning an informal get-together or a special event, we’ll help you find a comfy space to fit the occasion.
Are there holiday homes in St. Michaels that welcome kids?
St. Michaels has eight family-friendly holiday homes to pick from. And booking a stay that welcomes children is super easy with our “Properties good for families” filter. On top of having the entire place to yourselves, you’ll also get perks and conveniences such as extra bedrooms, full kitchens and private pools.
What are the top attractions for families in St. Michaels?
Keep your kids busy at these top family-friendly attractions in St. Michaels:

  • Chesapeake Bay Maritime Museum
  • St. Michaels Museum
  • Historical Society of Talbot County

Can I find two-bedroom holiday homes in St. Michaels?
Take off with your besties and relax in total privacy and comfort in one of the five two-bedroom holiday properties St. Michaels has to offer.
Are there holiday homes with WiFi in St. Michaels?
Whether you’d like to keep up with the latest news, check emails or update your social media, there are two holiday homes with WiFi in St. Michaels. Check the “WiFi” box when searching on Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in St. Michaels?
Decide on your travel dates and then make use of our filters to locate holiday homes with air conditioning in St. Michaels on Stayz. With eight air-conditioned properties on offer here, you can enjoy a comfy and cool stay.
How old do you have to be to rent a holiday home in St. Michaels?
The minimum age requirements can differ between properties on Stayz, so be sure to look at the rules of the holiday home in St. Michaels you’re interested in. But normally, it’s 16, 18 or 21.
How long can I rent a holiday home in St. Michaels for?
The amount of time you can stay in a St. Michaels holiday home for varies depending on the property. Just put in your preferred travel dates to see available options that offer long-term stays. They come with all you need to make your extended holiday more comfortable and convenient, such as kitchens and air conditioning. Some holiday homes may also offer weekly or monthly discounts, so you can stay even longer for less.

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