St. Michaels holiday rentals

We found 198 holiday rentals — enter your dates for availability
Discover a selection of 35 homes and other holiday rentals in St. Michaels that are 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.

Holiday rentals with weekly discounts – St. Michaels

Showing deals for:25 Dec - 1 Jan

Dining table- seats 10!
Pool
screened porch
View from Foyer into Great Room
Exceptional
(146 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

8% off
AU$11,041
for 7 nights, 1 home
AU$1,577 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Thomas Harrison House looking from St. Michaels Town Harbor
View of Side of Harrison House and St. Michaels Harbor from Locust Street
View of St. Michaels Harbor from Town Park in front of Thomas Harrison House
Rear Porch for relaxing or for barbecues!
Exceptional
(145 reviews)

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

St. Michaels

8% off
AU$8,621
for 7 nights, 1 home
AU$1,232 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Interior
The view off of the point, breathtaking.
Pool
Interior
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
AU$6,686
for 7 nights, 1 home
AU$955 per night
includes taxes & fees
Grandview- Main House
Living area
Dining
Private kitchen
Private kitchen
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
AU$5,387
for 7 nights, 1 cottage
AU$770 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Custom kitchen
View down the lane
Living Room with flat screen TV and sleeper sofa
Sit and stay a while!
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,819
for 7 nights, 1 cottage
AU$403 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Exterior
Living area
Interior
Private kitchen
Exceptional
(51 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

8% off
AU$9,051
for 7 nights, 1 home
AU$1,293 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Interior
Private kitchen
Property grounds
Interior
Exceptional
(7 reviews)

Arcadia Shores on the Cove.

Easton

8% off
AU$6,791
for 7 nights, 1 home
AU$970 per night
includes taxes & fees
Arcadia Shores on the Cove.
Interior
Be ready to float! Bring your own inner tubes and tennis shoes!
Exterior detail
Living area
Exceptional
(144 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
AU$2,886
for 7 nights, 1 cottage
AU$412 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Private kitchen
Exterior
Living area
Property grounds
Exceptional
(25 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman

8% off
AU$4,084
for 7 nights, 1 cottage
AU$583 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Private kitchen
Living area
Interior
Property grounds
Exceptional
(415 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

17% off
AU$2,860
for 7 nights, 1 home
AU$409 per night
includes taxes & fees
Stay in the HEART of Saint Michaels!

  • 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 (14.4 mi / 23.1 km)
  • Chesapeake Beach Water Park (18 mi / 29 km)
  • Paul Reed Smith Guitars (14.7 mi / 23.7 km)
  • U.S. Naval Academy Golf Club (19.4 mi / 31.2 km)
  • Phillips Wharf Environmental Center (7.5 mi / 12.1 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:

  • Northern Chesapeake Bay (13.9 mi / 22.4 km)
  • Gerry Boyle Park at Great Marsh (16 mi / 25.8 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)
  • Sandy Point Beach (18.1 mi / 29.1 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 rental?
When looking for the best area to stay in St Michaels, Maryland, a delightful choice is the historic downtown district. This charming area is characterised by its picturesque streets, quaint boutiques, and waterfront views, making it an ideal setting for a relaxing holiday. You'll find a range of holiday rentals here, from cosy cottages to elegant homes, offering a variety of options to suit different preferences.St Michaels is renowned for its maritime heritage, and staying in the downtown area puts you within walking distance of the Chesapeake Bay Maritime Museum, which is a top attraction that showcases the region's rich nautical history. Additionally, the nearby waterfront parks, such as the charming Muskrat Park, provide lovely spots for picnics and leisurely strolls.Another appealing neighbourhood to consider is the area surrounding the beautiful St Michaels Harbour. This location offers a mix of waterfront properties and easy access to various dining options, allowing guests to enjoy the local cuisine. The scenic views of the water and the opportunity for boating activities enhance the overall experience.
Where are the best areas for renting a beach house in St Michaels?
For renting a beach house in St Michaels, consider the picturesque waterfront along the Chesapeake Bay. The area near the St Michaels Harbour Inn offers beautiful holiday rentals with stunning views of the water, often featuring amenities such as private balconies, outdoor dining areas, and fully equipped kitchens, superb for families or groups looking to enjoy a relaxing getaway.Additionally, properties located close to the historic downtown area provide easy access to charming shops, art galleries, and local eateries, enhancing the overall experience. Many of these rentals come with features like private docks, allowing guests to explore the bay by boat or kayak.The nearby Chesapeake Bay Maritime Museum is a must-visit for those interested in the local maritime heritage, and many accommodations are within walking distance to this cultural landmark.
What is the most popular type of holiday rental accomodation in St Michaels?
In St Michaels, holiday houses are the most popular type of holiday rental, with around 128 available across the charming town. These houses often come with spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios, ideal for enjoying the picturesque views of the Chesapeake Bay. Additionally, there are approximately 52 cottages, which provide a quaint and cosy atmosphere, typically featuring rustic decor and amenities like fireplaces and gardens. For those preferring a more compact option, about 20 apartments can be found, usually offering modern conveniences including kitchen facilities and living areas.
Are there any family house rentals in St Michaels?
In St Michaels, Maryland, there are numerous family-friendly house rentals available, with around 38 options to choose from. This charming town, located along the Eastern Shore, offers a delightful mix of waterfront views and historical charm, making it an ideal destination for families.Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to play and explore. Visitors can enjoy amenities such as private patios, BBQ grills, and sometimes even access to docks for boating adventures.The neighbourhood is close to points of interest like the Chesapeake Bay Maritime Museum, where families can learn about the local maritime history, and the scenic St Michaels waterfront, which is great for leisurely strolls or bike rides. Additionally, the area boasts various shops and eateries, allowing families to immerse themselves in local culture while enjoying a relaxing holiday.
Can I rent a holiday home with a pool or hot tub in St Michaels?
In St Michaels, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 23 options to choose from. This charming town, situated on Maryland's Eastern Shore, offers a delightful blend of waterfront views and quaint historic charm. Many of these properties come equipped with private pools, inviting hot tubs, and spacious outdoor areas, superb for enjoying the pleasant climate.Travellers can expect amenities such as fully equipped kitchens, comfortable living spaces, and often outdoor dining areas, which enhance the experience of relaxation and leisure.
Are there pet-friendly house rentals in St Michaels?
In St Michaels, there are a variety of pet-friendly house rentals available, with around 28 options to choose from. This charming waterfront town offers holiday homes that often feature spacious interiors, outdoor patios, and fully equipped kitchens, making them great for families and groups travelling with pets. Many properties are situated close to the picturesque St Michaels Harbour, providing stunning views and easy access to the water.The area is also known for its delightful parks and outdoor spaces, such as the nearby Chesapeake Bay Maritime Museum grounds, which are great for leisurely walks with pets. Additionally, the town has a number of pet-friendly restaurants and cafes, allowing visitors to enjoy local cuisine while accommodating their furry companions.
Are there any remote work holiday rentals in St Michaels?
In St Michaels, Maryland, there is a wide selection of remote work holiday rentals available, with around 192 options for travellers to choose from. This charming town, known for its picturesque waterfront and rich maritime history, offers a variety of properties suitable for those looking to work remotely while enjoying a relaxing getaway. Many of these rentals come equipped with high-speed internet and free Wi-Fi, ensuring that guests can stay connected and productive during their stay.Expect to find comfortable living spaces with dedicated work areas, as well as inviting amenities such as fully equipped kitchens, spacious dining areas, and outdoor patios for taking breaks and enjoying the beautiful surroundings. St Michaels is also home to local attractions like the Chesapeake Bay Maritime Museum, scenic parks, and delightful shops and restaurants, which offer opportunities for leisure and exploration during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in St Michaels?
In St Michaels, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals and enjoy the local flavours of Maryland. Many properties also offer onsite parking, making it convenient for those travelling by car. For a refreshing start to the day, rentals typically feature coffee and tea makers, ensuring that guests can enjoy their morning beverages at leisure. Additionally, many accommodations come with decks or patios, providing lovely outdoor spaces to relax and take in the scenic surroundings. Some properties even permit pets, making it easier for travellers to bring their furry friends along for the stay.
When is the best time to visit St Michaels for a holiday rental?
The best time to visit St Michaels for a holiday rental is during the peak season from June to August, with July being the most popular month. This summer period draws in visitors keen to enjoy the charming atmosphere, warm weather, and vibrant local events. It's an ideal time for outdoor activities such as boating on the Chesapeake Bay, exploring the picturesque streets lined with historic buildings, or indulging in the local seafood cuisine.Temperatures in St Michaels during these months typically range from the mid-teens to high twenties Celsius, providing a comfortable climate for sightseeing and relaxation. The town comes alive with festivals, art shows, and live music, making it a superb destination for those looking to immerse themselves in the local culture while enjoying the scenic waterfront.For those seeking a more budget-friendly option, consider visiting in November. This month offers a quieter experience, allowing you to explore the area's natural beauty and historical sites without the crowds. You can enjoy peaceful walks along the waterfront and take in the stunning autumn scenery, which has its own unique charm.Ultimately, your choice of when to visit St Michaels should align with your preferences for lively summer activities or a more tranquil autumn getaway.
What are the top attractions in St Michaels?
In St Michaels, visitors can enjoy a variety of attractions that highlight the area's rich maritime history and charming coastal atmosphere. The Chesapeake Bay Maritime Museum is a must-see, offering insights into the local culture and history, along with beautiful views of the waterfront. The museum is conveniently located near many holiday rentals, making it easy for guests to explore.The picturesque streets of St Michaels are lined with quaint shops and art galleries, great for leisurely strolls. The town's historic district features lovely architecture and several waterfront dining options where guests can savour fresh seafood while enjoying views of the bay.For those interested in outdoor activities, the nearby St. Michaels Nature Park offers trails for walking and birdwatching, while the surrounding waters provide opportunities for kayaking and sailing.
Are all fees included in the St. Michaels holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any St. Michaels holiday homes with parking?
Stayz offers a wide selection of holiday homes in St. Michaels with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for St. Michaels holiday homes?
You can find great discounts on holiday homes in St. Michaels on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my St. Michaels holiday home booking on Stayz?
To find St. Michaels holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in St. Michaels?
A long-stay holiday home in St. Michaels is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a St. Michaels holiday home?
Book your St. Michaels holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in St. Michaels?
Prices for holiday homes in St. Michaels vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in St. Michaels to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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