St. Michaels holiday lettings

We found 198 holiday rentals — enter your dates for availability

Select from 34 homes, 14 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.

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Why visit St. Michaels

  • Charming historical streets: St. Michaels boasts picturesque streets rich in history, perfect for leisurely strolls.
  • Outdoor activities: Enjoy a variety of outdoor pursuits, from boating to cycling, in a stunning natural setting.
  • Cultural experiences: Explore local attractions such as the history museum and environmental centre for enriching insights.
  • Family-friendly excursions: Discover attractions suitable for all ages, making it an ideal destination for families.
  • Comfortable accommodations: Choose from charming cottages and stylish apartments for a relaxing stay.

Popular types of accommodation in St. Michaels

If you’re pondering the ideal accommodation for your getaway in St. Michaels, look no further. Our most sought-after options include houses, charming cottages, and stylish apartments. Whether you’re searching for St. Michaels holiday rentals or house rentals, we aim to provide a selection that ensures comfort and relaxation. Explore our vacation rentals and discover your perfect home away from home in this delightful destination.

  • Houses: The top choice for visitors in St. Michaels, offering spacious accommodations perfect for families, friends, or couples seeking a home-like experience.
  • Cottages: A delightful option for a quaint and cosy stay, ideal for those who appreciate charm and a touch of tranquillity.
  • Apartments: Convenient and versatile, these lodgings provide a modern living space for those wanting easy access to local amenities.
  • Condos: A popular choice with added comforts, perfect for guests looking for a blend of luxury and convenience.
  • Cabins: Offering a rustic escape, these are perfect for nature enthusiasts wanting to immerse themselves in the great outdoors.**

Top attractions in and around St. Michaels

St. Michaels, Maryland, is an idyllic destination for outdoor enthusiasts, families, and romantic getaways. Visitors can explore a range of attractions, including the local history museum, marina, and environmental centre, all of which provide enriching cultural experiences. Don't miss the opportunity to delve into the historic charm of St. Michaels, making it a perfect spot for a memorable holiday.

  • Chesapeake Bay Maritime Museum: An engaging maritime museum that celebrates the rich maritime heritage of the Chesapeake Bay. Visitors can explore historic vessels, interactive exhibits, and enjoy beautiful waterfront views that reflect the area's culture.
  • St. Michaels Museum: A charming history museum that showcases the local history of St. Michaels and its surrounding areas. The museum features artefacts and exhibits that provide insight into the town's cultural heritage.
  • Pickering Creek Audubon Center: An eco-friendly environmental centre located 4.3km from St. Michaels, dedicated to conservation and education. Visitors can enjoy nature trails, birdwatching, and various programmes focused on local wildlife and ecosystems.

Things to do recommended for couples

St. Michaels offers delightful couple experiences, from wine tasting at the charming St. Michaels Winery to indulging in relaxation at Talbot Massage, just 5.6km away. For adventure lovers, the Annapolis Sailing School, 11.2km distant, promises thrilling outdoor escapades on the water.

Things to do recommended for families

Families visiting St. Michaels, Maryland, can have a splashing good time at Chesapeake Beach Water Park, located 11.2km away. This vibrant waterpark offers an array of entertainment and adventure, perfect for creating lasting memories together.

Things to do recommended for groups

Enjoy a cultural evening at the Avalon Theatre, only 5.0km from St. Michaels, or challenge your friends at Hog Neck Golf Course, 5.6km away. For a shopping spree, head to Queenstown Premium Outlets, 8.7km distant, offering a variety of shops and family-friendly fun.

What do I need to keep in mind when booking a vacation in 'St. Michaels

If you’re travelling with a group, with family, bringing your pets, or seeking extended stays, be sure to refine your search according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to St. Michaels with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to St. Michaels with young kids: Travelling with young children can present its own set of challenges. It’s important to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it would be wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to St. Michaels: For many, a family holiday wouldn’t feel complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting St. Michaels: If you're in search of holiday rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in and around St. Michaels

St. Michaels offers a delightful blend of outdoor adventures and romantic escapes, perfect for families or a memorable getaway. Explore the charming streets steeped in history, enjoy sunny weather, and savour the relaxing atmosphere of this picturesque town. Nearby, you'll find family-friendly attractions and excursions that cater to all ages, making it an ideal destination for long stays and unforgettable experiences. Discover the allure of St. Michaels, where every moment is a cherished memory waiting to be made.

  • Easton: Situated 5.0km from St. Michaels, Easton is a charming city known for its vibrant outdoor activities and family-friendly atmosphere. Visitors can enjoy a stroll along the scenic boardwalk, indulge in retail therapy at the shopping centre or mall, and take in the local sights. Notable attractions include the family beach, where you can relax and soak up the sun, and historical monuments that narrate the area’s rich heritage. Easton’s blend of romance and adventure makes it a delightful day trip for couples and families alike.
  • Bozman: Located just 1.9km away, Bozman is a picturesque city perfect for those seeking outdoor escapades and romantic scenery. With its inviting recreational areas and serene boardwalks, Bozman offers a peaceful retreat into nature. The proximity to both a family beach and a tranquil lake presents ample opportunities for swimming, picnicking, or simply enjoying the stunning views. Whether you're a nature enthusiast or a couple looking for a romantic getaway, Bozman’s idyllic landscape is sure to captivate your heart.
  • Claiborne: Nestled within the St. Michaels area, Claiborne is a quaint village that invites visitors to explore its natural beauty and historic charm. The serene surroundings are ideal for outdoor pursuits, with a lovely beach and a picturesque lake nearby. History buffs will appreciate the historic house that adds character to this small community. Claiborne’s tranquil ambiance and scenic vistas create a perfect backdrop for a romantic escape or a leisurely day spent in nature.

Best time to go to St. Michaels

If you're planning a trip to St. Michaels, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.3°F (2.4°C)Light RainMostly SunnyModerately LowSlightly Low
February38.8°F (3.8°C)Light RainMostly SunnyAverageSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyAverageSlightly Low
April55.6°F (13.1°C)Light RainMostly SunnyModerately HighAverage
May64.6°F (18.1°C)Light RainMostly SunnyAverageAverage
June73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
July78.4°F (25.8°C)Light RainMostly SunnyModerately HighSlightly High
August76.8°F (24.9°C)Light RainMostly SunnyAverageSlightly High
September71.1°F (21.7°C)Light RainMostly SunnyAverageAverage
October61.0°F (16.1°C)Light RainMostly SunnyAverageAverage
November49.5°F (9.7°C)Light RainMostly SunnyModerately LowAverage
December42.3°F (5.7°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming journey? We recommend considering flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the ideal Vrbo property that suits your budget, feel free to utilise our filters to organise results by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy area for you to plan new journeys, resume your previous arrangements, or manage your travel plans effectively. You can easily find the properties you’ve saved or booked, organised into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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 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)
  • Hog Neck Golf Course (9.4 mi / 15.1 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)
  • Northern Chesapeake Bay (13.9 mi / 22.4 km)
  • Triton Beach (15.9 mi / 25.6 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)

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.
How much does it cost to rent a holiday home in St Michaels?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in St Michaels to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for St Michaels holiday house rentals?
You can find great discounts on house rentals in St Michaels on Vrbo, 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.
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.
Can I find long-stay holiday rentals in St Michaels?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any St Michaels holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a St Michaels holiday rental?
Book your St Michaels holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my St Michaels home rental booking on Vrbo?
To find St Michaels holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the St Michaels holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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