St. Michaels vacation rentals

We found 202 vacation rentals — enter your dates for availability

Select from 33 homes, 15 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.

Vacation rentals with weekly discounts - St. Michaels

Showing deals for:May 1 - May 8

Image gallery for Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

House and Garage as seen from above (pool on left)
10 out of 10, Exceptional, (91 reviews)
Exceptional
(91 reviews)

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Royal Oak

9% off
Price is $2,374
$16,618 for 7 nights
All fees included
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

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 Club (14.4 mi / 23.1 km)
  • Chesapeake Beach Water Park (18 mi / 29 km)
  • Hog Neck Golf Course (9.4 mi / 15.1 km)
  • Queenstown Harbor Golf Links (14.3 mi / 23.1 km)
  • Paul Reed Smith Guitars (14.7 mi / 23.7 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)
  • 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)

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 when booking a vacation rental?
When considering a vacation rental in St. Michaels, Maryland, a popular area to stay is the waterfront district, particularly near the harbor. This charming neighborhood not only offers stunning views of the Chesapeake Bay but also provides easy access to several top attractions, such as the Chesapeake Bay Maritime Museum, where you can immerse yourself in local maritime history and culture. The picturesque streets are lined with boutique shops, art galleries, and delightful restaurants, making it a great spot for leisurely strolls.

Another great option is the area around Talbot Street, which is known for its quaint ambiance and proximity to the St. Michaels Museum. This neighborhood boasts a variety of vacation rentals, so you are likely to find a range of properties that suit different preferences and budgets. The vibrant community atmosphere and the easy access to nearby parks and walking trails enhance the appeal of this area, providing a great blend of relaxation and exploration during your stay.
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, Maryland, travelers should consider properties along the waterfront near the charming downtown area, which is known for its historic architecture and vibrant local culture. This region offers a selection of waterfront rentals with stunning views of the Chesapeake Bay. Many of these houses feature amenities such as private docks, outdoor decks, and spacious living areas, making them great for families or groups eager to enjoy the serene waters and surrounding nature.

Additionally, the area around St. Michaels is rich in recreational options. Vacation rentals near the St. Michaels Museum often come with easy access to biking and walking trails, providing opportunities for exploring the picturesque scenery. Many properties in this vicinity may also include kayaks or bicycles for guest use, enhancing the experience of the area's natural beauty.

For those interested in dining and shopping, the downtown St. Michaels area is home to boutique shops, art galleries, and a variety of restaurants serving fresh seafood and local cuisine. Rentals near this area tend to offer convenient access to these amenities while providing a cozy retreat to unwind after a day of exploration. Find your rental near the beach in St Michaels.
What is the most popular type of vacation rental accomodation in St Michaels?
In St. Michaels, vacation houses are the most popular type of rental, with about 35 available throughout the charming town. These houses often offer spacious living areas, fully equipped kitchens, and outdoor spaces like porches or decks, superb for enjoying the picturesque views of the Chesapeake Bay.

Additionally, there are around 13 cottages that provide a cozy and quaint atmosphere, ideal for couples or small families looking for a more intimate setting. While apartments, cabins, and villas are less common, several options are available for those seeking different experiences.
Are there any family house rentals in St Michaels?
In St. Michaels, Maryland, families will find a variety of suitable vacation rentals, with around 35 options available throughout the area. The charming town, located along the Chesapeake Bay, offers a picturesque backdrop for family getaways. Many homes come equipped with spacious living areas, fully stocked kitchens for preparing meals, and outdoor spaces ideal for barbecues or relaxing evenings under the stars.

Visitors can also expect amenities like Wi-Fi, air conditioning, and sometimes even game rooms or private docks, superb for those looking to explore the water. The town's proximity to attractions like the Chesapeake Bay Maritime Museum and the scenic St. Michaels Harbor enhances the experience, providing opportunities for educational outings and leisurely strolls. 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, you can find a variety of vacation homes available for rent that feature pools and hot tubs, with around 25 options to choose from. This picturesque town, located along the Chesapeake Bay, offers a charming setting with beautiful waterfront views. Many of these rentals provide amenities such as private pools, inviting hot tubs, spacious outdoor decks, and fully equipped kitchens, making them great for families or groups looking to relax and unwind.

Travelers can also enjoy proximity to local attractions, including quaint shops, delicious restaurants, and scenic marinas, enhancing the overall experience. Find your rental in St Michaels with a pool or a hot tub.
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, offering a charming escape on the Eastern Shore of Maryland. Many of these rentals feature amenities such as spacious outdoor decks, fully equipped kitchens, and cozy living areas, making them ideal for families traveling with pets. Some properties provide fenced yards, allowing pets to roam safely while enjoying the beautiful surroundings.

The picturesque town is near the waterfront, with easy access to local parks and pet-friendly areas. For example, St. Michaels Park offers open spaces and walking trails, superb for leisurely strolls with your furry friends. See all pet-friendly rentals in St Michaels.
Are there any remote work vacation rentals in St Michaels?
In St. Michaels, Maryland, there are numerous remote work vacation rentals available, with around 46 options to choose from. This picturesque waterfront town offers a serene environment superb for combining work and relaxation. Many of these rentals come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated office spaces, desks, and comfortable desk chairs, ensuring that you can stay productive during your stay.

The charming historic district of St. Michaels features quaint shops, local eateries, and stunning views of the Chesapeake Bay, providing a great backdrop for breaks from work. Additionally, the area offers opportunities for outdoor activities, such as kayaking and biking, allowing you to unwind after a productive day. 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 vacation rental amenities include WiFi, kitchens, and coffee/tea makers, which are essential for travelers looking for convenience and comfort during their stay. Many rentals also feature private pools, providing a great spot for relaxation after a day of exploring the charming waterfront town. Onsite parking is another common amenity, making it easier for guests to navigate the area and visit nearby attractions, such as the Chesapeake Bay Maritime Museum and local shops.
When is the best time to visit St Michaels for a vacation rental?
The best time to visit St. Michaels for a vacation rental is during the peak season from June to August. This vibrant period attracts travelers seeking sun-soaked days along the Chesapeake Bay, with July being the most popular month. Visitors can experience firsthand a variety of outdoor activities, such as boating, kayaking, or simply enjoying leisurely strolls along the charming waterfront.

During the summer, temperatures typically range from the mid-70s to mid-90s Fahrenheit, providing a warm and inviting climate great for exploration and relaxation. The lively atmosphere is complemented by local festivals and events, making it an exceptional time for families and friends to create lasting memories together.

For those looking for a more budget-friendly option, consider planning your visit in November. While the weather may be cooler, with temperatures averaging in the low to mid-50s Fahrenheit, this month offers a unique opportunity to experience St. Michaels in a quieter, more peaceful setting.
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?
In St. Michaels, visitors can enjoy a charming selection of attractions throughout the town. The St. Michaels Museum offers insights into local history and culture, showcasing artifacts and exhibits related to the area's maritime heritage. Nearby, the Chesapeake Bay Maritime Museum presents a deeper dive into the region's connection to the water, featuring historic vessels and interactive displays.

The picturesque waterfront makes the downtown area ideal for leisurely strolls, where travelers can discover unique shops, art galleries, and local restaurants serving fresh seafood. The nearby Miles River provides opportunities for boating and kayaking, adding to the outdoor experience.

For those interested in nature and wildlife, the St. Michaels area is close to the beautiful Chesapeake Bay, where visitors can explore scenic trails and birdwatching spots.
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.

More Vacation Ideas