St. Michaels Vacation Rentals from CA $137: Short-Term Rentals for 2025

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Vacation Rentals in St. Michaels

Our top choices for St. Michaels vacation rentals

"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "

"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"

"Good location, clean house, easy check in and check out process."

"We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage."

"Clean and nice place to stay"

"We had 14 family members join us to celebrate my son’s graduation from the Naval Academy. The house is clean, the rooms were great, the property was beautiful, and it was close to USNA. Our family loved the open concept. "

"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."

"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."

CA $684 total

includes taxes & fees

Aug 26 - Aug 27

"Next time we will wait until its a little warmer! Safe and clean marina. Great views! Peaceful and quiet. "

"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "

"We really enjoyed our stay. Looking forward to staying again!"

CA $369 total

includes taxes & fees

Sep 7 - Sep 8

"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "

CA $523 total

includes taxes & fees

Aug 26 - Aug 27

"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"

"Just perfect for a 4 night stay."

"Loved the location and the pristine condition of the house. "

"This exceptional property was our best homestay experience yet across several states and countries. The unit has so many customized features that make it stand out, from the fire pit (fire already built) and sauna (water bucket already filled) to the kitchen and bedrooms, where no detail has been missed. The owners were extremely proactive and responsive throughout our stay, and we look forward to booking again soon. "

"Excellent location, Excellent property, Excellent owners!"

"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"

"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."

"Very roomy and lots of amenities. Superb location and private. Easy check-in and check-out. Guest contact was awesome - very responsive! Thanks so much!"

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Top St. Michaels Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"Great "

Hampton Inn & Suites Annapolis

10/10 Excellent

"It's poorly maintained. Baseboard in room coming off corner into the bathroom. Paint peeling off the bathroom door. Bathroom faucet was loose. The toilet seat was loose. Toilet runs on and off all the time. It was a very dark room, low wattage light bulbs and one of the lamps didn't work. There's a leak somewhere from the tub even when the shower curtain is closed and leaves a puddle. The Staff was very friendly though the lobby was old and dirty. We were supposed to stay there 6 days but left after the first night."

Courtyard by Marriott Annapolis

10/10 Excellent

"The staff was very friendly, our room and surrounding areas (hallway, courtyard, parking lot) were very clean. But somehow water would leak out of the shower and make a puddle on the floor. The carpet outside the tile in front of the closet would also get wet. We couldn't figure out how."

Sonesta ES Suites Annapolis

10/10 Excellent

"I wish we discovered this place 3 years ago. We have been coming in Us Naval Academy for the past 3 years and if I have found this place earlier, we would stayed in this hotel. My husband and I enjoyed our overnight stay. We will definitely consider this hotel again in our future visit in Annapolis."

Find out more about St. Michaels

Everything you need to know about St. Michaels vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the St. Michaels vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect St. Michaels vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

St. Michaels vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in St. Michaels. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A St. Michaels vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of St. Michaels vacation rentals we have selected for you start as low as CA $137 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on St. Michaels rentals

At Expedia, we put the best St. Michaels vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top St. Michaels rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream St. Michaels vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around St. Michaels. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in St. Michaels?

Yes, we have vacation rentals in St. Michaels close to Chesapeake Bay Maritime Museum, or you can choose a more secluded option if you're looking for a relaxing stay. The waterfront and shops are just a few reasons why tourists like St. Michaels. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best vacation rentals in St. Michaels?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: You might want to consider this vacation home rental near St. Michaels, which offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in St. Michaels?

Expedia has 33 vacation rentals for your stay in St. Michaels.

What’s there to see and do in St. Michaels?

Cultural attractions include Chesapeake Bay Maritime Museum and St. Michaels Museum, whereas Church Cove Park and CL Open Field are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include St. Michaels Marina and St. Michaels Winery.

What’s a vacation rental in St. Michaels like?

Vacation rentals are private properties where you can stay for short or long periods in St. Michaels. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.

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St. Michaels Vacation Rentals

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Vacation Rentals in St. Michaels

Our top choices for St. Michaels vacation rentals

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Walk to Everything House

Walk to Everything House

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

Waterfront Getaway, Dock Your Boat & Play!

Waterfront Getaway, Dock Your Boat & Play!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Chesapeake Houseboat Getaway on Kent Island, Maryland

Chesapeake Houseboat Getaway on Kent Island, Maryland

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

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

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Private Cottage on gated estate

Private Cottage on gated estate

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Bay views with kayaks, bikes, fire pit, crabbing and more

Bay views with kayaks, bikes, fire pit, crabbing and more

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Top St. Michaels Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Find out more about St. Michaels

Find out more about St. Michaels

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Explore a world of travel with Expedia

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