St. Michaels vacation rentals

We found 199 vacation rentals — enter your dates for availability

Select from 34 homes, 14 cottages, and other vacation rentals in St. Michaels to find one that's perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the amenities you expect for your stay, which might include a fireplace and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about St. Michaels

Why visit St. Michaels

  • Outdoor Adventures: St. Michaels is perfect for kayaking, biking, and exploring the beautiful waterfront views.
  • Historical Excursions: Dive into the rich history with visits to local museums and historic sites.
  • Romantic Getaways: Enjoy cozy accommodations and scenic spots ideal for couples to unwind.
  • Family-Friendly Activities: The town offers a variety of attractions suitable for all ages, making it great for family trips.
  • Picturesque Surroundings: Experience the charm of this coastal town with its stunning natural landscapes.

Popular types of accommodation in St. Michaels

Planning a getaway to St. Michaels? You're in for a treat. This charming destination offers a variety of vacation rentals, including houses, cozy cottages, and stylish apartments. Whether you're searching for the best St. Michaels vacation rentals or friendly house rentals, you'll find the perfect spot to relax and enjoy the picturesque surroundings. Explore our selection of Saint Michaels vacation rentals and make your trip unforgettable.

  • Houses: These are the top choice for visitors, offering spacious and comfortable accommodations ideal for families or groups seeking a home-like atmosphere in St. Michaels.
  • Cottages: Charming and cozy, these quaint retreats provide a delightful escape, perfect for couples or small families wanting a picturesque setting.
  • Apartments: These versatile options are great for those looking for a convenient and flexible stay, often located near local attractions.
  • Condos: Providing amenities and often stunning views, condos are a popular choice for travelers seeking a blend of luxury and comfort.
  • Cabins: Rustic and inviting, cabins offer an authentic experience for nature lovers wanting to immerse themselves in the surrounding beauty.**

Top attractions in St. Michaels

St. Michaels, Maryland, is perfect for outdoor adventures and romantic getaways, offering a family-friendly atmosphere. Visitors can enjoy a variety of attractions, including marinas, history museums, and urban parks. Whether you're seeking cultural experiences or outdoor activities, St. Michaels has something for everyone. Explore the local charm and create lasting memories with your loved ones in this picturesque town.

  • Chesapeake Bay Maritime Museum: This engaging maritime museum showcases the rich maritime heritage of the Chesapeake Bay. Explore interactive exhibits, historic boats, and scenic waterfront views that highlight the region's culture and connection to the water.
  • St. Michaels Museum: Dive into local history at this charming museum, featuring artifacts and exhibits that tell the story of St. Michaels and its residents. The museum's cultural vibes provide a fascinating glimpse into the town's past.
  • Perry Cabin Park: A beautiful urban park perfect for families, offering walking trails, picnic spots, and stunning views of the harbor. It's an ideal place to relax outdoors and enjoy the vibrant atmosphere of St. Michaels.

Things to do recommended for couples

Ready for a romantic getaway in St. Michaels? Savor the charm at St. Michaels Winery, indulge in relaxation at Talbot Massage just 9 miles away, or embark on an adventure with Annapolis Sailing School 18 miles from town. Each experience promises unforgettable moments together.

Things to do recommended for families

Families visiting St. Michaels can enjoy an exciting day at Chesapeake Beach Water Park, located 18 miles away. This vibrant waterpark offers entertainment and adventure, making it a perfect spot for family fun and memorable experiences together.

Things to do recommended for groups

Explore the charming Saint Michaels Village for unique shopping experiences, enjoy a show at the nearby Avalon Theatre for a dose of culture and entertainment, and hit the links at Hog Neck Golf Course for a fun day of outdoor sports with your group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, pets, or planning an extended stay, be sure to use the appropriate filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to St. Michaels with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to St. Michaels with young kids: Traveling with young kids can be tough. It’s important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly activities.
  • Taking your pets with you to St. Michaels: For many families, a vacation isn’t truly finished without their furry companion by their side. If that resonates with you, explore Vrbo listings 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 vacation rentals that offer discounts 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 rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around St. Michaels

St. Michaels, Maryland, offers a delightful blend of outdoor adventures, romantic getaways, and family-friendly activities. Nestled on the Eastern Shore, this charming town is known for its picturesque spots and stunning natural surroundings. Explore beautiful waterfront views, indulge in historical excursions, and soak in the coastal feel. Nearby cities and neighborhoods provide a sunny, relaxing atmosphere, making St. Michaels a perfect destination for a memorable vacation experience.

  • Easton: Located 8 miles from St. Michaels, Easton is a vibrant city that offers a delightful mix of outdoor activities and family-friendly experiences. Visitors can enjoy leisurely strolls along the scenic boardwalk or explore the charming shopping centers and malls that dot the area. Easton is known for its beautiful local landmarks, including family beaches and historical monuments, making it a perfect destination for romantic getaways or fun-filled family vacations.
  • Bozman: Situated only 3 miles from St. Michaels, Bozman is a hidden gem that invites travelers to immerse themselves in nature. Known for its stunning scenery, this quaint city is ideal for outdoor enthusiasts and couples seeking a romantic escape. Bozman features picturesque recreational areas and inviting boardwalks that lead to serene beaches and tranquil lakes. It's a perfect spot to unwind and appreciate the natural beauty of Maryland's Eastern Shore.
  • Claiborne: Nestled in the vicinity of St. Michaels, Claiborne is a charming village that offers a peaceful retreat for visitors. Known for its scenic landscapes, this community is perfect for those who love outdoor activities. With access to beautiful lakes and inviting beaches, Claiborne provides a tranquil setting for relaxation and exploration. Don't miss the opportunity to visit the historic houses that tell the story of the area's rich heritage, making it an enriching stop on your journey.

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 a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can really help, as prices often vary. Additionally, booking a longer stay typically leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn all the OneKeyCash on your booking. Being the planner definitely has its perks. By signing up for our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash on eligible reservations. Join us today and start enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume previous ones, or manage your travel arrangements. You’ll find your saved or booked properties neatly organized into three categories: Potential, Upcoming, and Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Head to the historic city of St. Michaels

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

Sightseeing in and around St. Michaels

Are you searching for attractions to see during your stay? Venture out of your cozy vacation rental and experience everything that makes St. Michaels a one-of-a-kind vacation spot. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Paul Reed Smith Guitars (14.7 mi / 23.7 km)
  • Chesapeake Beach Water Park (18 mi / 29 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 appreciate the scenery, you'll be sure to find the perfect setting for your vacation in St. Michaels. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Chesapeake Bay Environmental Center (11.2 mi / 18 km)
  • 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)

Transportation 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 center. If you're unable to find a flight that fits your schedule, you can also fly into 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, Maryland, United States of America when booking a vacation rental?
When looking for the best area to stay in St. Michaels, Maryland, you might consider the charming neighborhoods near the waterfront. The area is known for its picturesque scenery and a relaxed atmosphere, making it ideal for a vacation rental. One popular neighborhood is close to the harbor, where you'll find a lovely selection of vacation homes that offer stunning views of the Chesapeake Bay.

Staying in this area gives you easy access to top attractions like the Chesapeake Bay Maritime Museum, which showcases the region's rich maritime history and features beautiful exhibits and outdoor spaces. Another delightful point of interest nearby is the iconic St. Michaels lighthouse, superb for a leisurely stroll and some unforgettable photo opportunities.

In terms of properties, there are a variety of vacation rentals available, ranging from cozy cottages to luxurious waterfront homes. This diversity allows visitors to choose accommodations that best fit their needs and preferences.
How much does it cost to rent a vacation home in St Michaels?
Prices for vacation 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 vacation 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, travelers should explore the waterfront areas along the Miles River, particularly near the historic downtown area. This charming town offers a variety of vacation rentals that feature picturesque views of the water and convenient access to boating and fishing activities. Many properties come equipped with amenities such as private docks, outdoor seating areas, and full kitchens, making them superb for families or groups looking to enjoy a relaxing getaway.

Additionally, the neighborhoods surrounding the St. Michaels Museum and the Chesapeake Bay Maritime Museum provide an enticing blend of history and recreation. Rentals in this area often include features like spacious decks for entertaining, fire pits for evening gatherings, and easy access to local shops and restaurants. The proximity to the scenic bike paths and walking trails along the water enhances the overall experience for visitors looking to immerse themselves in the natural beauty of the region.

For those interested in exploring the nearby natural attractions, properties located near the St. Michaels Nature Trail offer a peaceful retreat with the opportunity for hiking and birdwatching. These rentals may come with private gardens or outdoor spaces ideal for enjoying the serene surroundings.
What is the most popular type of vacation rental accomodation in St Michaels?
In St. Michaels, vacation houses are the most popular rental option, with about 32 available throughout the charming waterfront town. These houses typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them great for families or groups. Many of these properties also come with outdoor spaces such as decks or patios, allowing guests to enjoy the picturesque views of the Chesapeake Bay.

Additionally, there are around 13 cottages that provide a more quaint and cozy atmosphere, often located near the historic district and local attractions. These cottages usually have unique character and charm, featuring amenities like fireplaces and private gardens. While there are several apartments available, they tend to be less common than houses and cottages.
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 is known for its picturesque waterfront and rich maritime history, making it an ideal spot for families looking to enjoy a relaxing getaway. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play or enjoy a barbecue.

Visitors can find homes with amenities like Wi-Fi, air conditioning, and some even offer private docks for easy access to the water. The town is also close to attractions such as the Chesapeake Bay Maritime Museum and local shops and restaurants, allowing families to immerse themselves in the local culture. See all family-friendly rentals in St Michaels.
Can I rent a vacation home with a pool or hot tub in St Michaels?
In St. Michaels, Maryland, there are several vacation homes available for rent that feature pools and hot tubs, with around 23 options to choose from. This charming waterfront town is known for its picturesque harbor and rich maritime history, making it an appealing destination for travelers seeking relaxation.

Many of the vacation rentals in St. Michaels come with amenities such as private pools, hot tubs, outdoor patios, and fully equipped kitchens, superb for families or groups looking to unwind after a day of exploring. Some properties may also include features like fire pits, spacious living areas, and access to nearby attractions, enhancing the overall experience.
Can I find long-stay vacation rentals in St Michaels?
A long-stay vacation rental in St Michaels is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in St Michaels?
In St. Michaels, there are several pet-friendly house rentals available, with a total of 28 options for travelers. Many of these properties are situated along the picturesque waterfront, offering stunning views of the Chesapeake Bay. Travelers can expect a variety of amenities, such as fully equipped kitchens, spacious living areas, and outdoor spaces that are superb for enjoying the pleasant Maryland weather. Some rentals may also include features like private docks, patios, and fire pits, making them ideal for families or groups traveling with pets.

The town itself is known for its charming atmosphere, and pet owners will appreciate the nearby parks and walking trails, which provide ample opportunities for outdoor exploration with their furry companions.
Are there any remote work vacation rentals in St Michaels?
In St. Michaels, Maryland, there are numerous remote work-friendly vacation rentals available, with about 48 options to choose from. This charming waterfront town offers a blend of scenic views and a peaceful atmosphere, making it an ideal spot for those looking to balance work and leisure. Many of the rentals come equipped with amenities tailored for remote work, such as high-speed internet, Wi-Fi access, and dedicated office spaces or desks in the units.

Travelers can expect comfortable living arrangements, often featuring fully equipped kitchens, spacious living areas, and outdoor spaces to enjoy the beautiful surroundings. St. Michaels is known for its picturesque historic district, quaint boutiques, and local eateries, providing plenty of opportunities for relaxation and exploration after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any St Michaels vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in St Michaels with parking available—perfect for families or travelers 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 rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals and enjoy home-cooked dining during their stay. Onsite parking is also a common feature, making it convenient for guests with vehicles. Many rentals offer coffee and tea makers, superb for starting the day with a warm beverage. Outdoor spaces such as decks or patios are prevalent, providing a lovely area to relax and take in the scenic views of the area. Additionally, some properties are pet-friendly, allowing travelers to bring their furry companions along for the trip.
When is the best time to visit St Michaels for a vacation rental?
The best time to book a vacation rental in St. Michaels is during the peak season from June to August, especially in July when the town comes alive with vibrant energy and numerous outdoor activities. This summer period is ideal for travelers seeking a mix of relaxation and adventure, as the warm weather invites you to explore the picturesque waterfront, indulge in fresh seafood, and enjoy various festivals and events.

During these months, you can expect temperatures to range from the mid-70s to low 90s Fahrenheit, making it great for sailing, kayaking, or simply lounging by the Chesapeake Bay. The charming streets of St. Michaels are bustling with visitors, offering a lively option where you can mingle with both locals and fellow travelers.

If you're looking for a more budget-friendly experience, consider visiting in November. This month provides a quieter retreat, allowing you to appreciate the serene beauty of St. Michaels without the hustle and bustle of the summer crowds. The crisp autumn air is great for scenic walks along the waterfront and exploring the region's rich history at local museums.

Ultimately, your choice will depend on whether you crave the lively summer ambiance full of activities or the peaceful charm of the fall season.
How early should I book a St Michaels vacation rental?
Book your St Michaels vacation 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 vacation 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, Maryland, United States of America?
In St. Michaels, visitors can engage in a charming maritime atmosphere while exploring a variety of attractions. The St. Michaels Museum offers a glimpse into the town's rich history and heritage, showcasing artifacts and exhibits related to the area's maritime past.

The Chesapeake Bay Maritime Museum is another highlight, featuring interactive exhibits, historic vessels, and beautiful waterfront views, making it a superb spot for families and history enthusiasts alike.

For outdoor lovers, the nearby Miles River provides opportunities for kayaking, sailing, and fishing, with several rental options available along the waterfront.

St. Michaels is also home to quaint shops, art galleries, and local restaurants that reflect the region's culinary scene, particularly its famous seafood.
Can I change or cancel my St Michaels home rental booking on Vrbo?
To find St Michaels vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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