St. Michaels Vacation Rentals

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Our top choices for St. Michaels vacation rentals

10.0 out of 10, Exceptional, (17)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
$292 nightly
The price is $322
Jan 11 - Jan 12, 2026
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
9.8 out of 10, Exceptional, (11)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
$314 nightly
The price is $333
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
$2,753 nightly
The price is $3,138
Dec 25 - Dec 26
Total with taxes and fees
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
10.0 out of 10, Exceptional, (7)
$245 nightly
The price is $260
Jan 14 - Jan 15, 2026
Total with taxes and fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
9.6 out of 10, Exceptional, (20)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
$322 nightly
The price is $341
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
$327 nightly
The price is $347
Jan 5 - Jan 6, 2026
Total with taxes and fees
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
$269 nightly
The price is $285
Dec 30 - Dec 31
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$260 nightly
The price is $275
Jan 5 - Jan 6, 2026
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
$240 nightly
The price is $254
Dec 26 - Dec 27
Total with taxes and fees
Sailwinds Loft at Cambridge Creek

Condo in Arundel on the Bay

Cozy Retreat w/Private Beach Access
2.0 star property
$146 nightly
The price is $167
Dec 30 - Dec 31
Total with taxes and fees
Cozy Retreat w/Private Beach Access
8.4 out of 10, Very Good, (6)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
$269 nightly
The price is $285
Jan 12 - Jan 13, 2026
Total with taxes and fees
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Condo in Historic District

Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
$529 nightly
The price is $603
Jan 1 - Jan 2, 2026
Total with taxes and fees
Upscale Condo in Annapolis
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
$260 nightly
The price is $276
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$369 nightly
The price is $407
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
$352 nightly
The price is $373
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Dec 29 - Dec 30
Total with taxes and fees
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
$420 nightly
The price is $445
Jan 5 - Jan 6, 2026
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
10.0 out of 10, Exceptional, (1)
$189 nightly
The price is $192
Jan 21 - Jan 22, 2026
Total with taxes and fees
Sailboat Experience in Annapolis
10.0 out of 10, Exceptional, (1)
"Great stay, host was super amazing and we had the best time!!"
United States
Kirstyn I.
$264 nightly
The price is $269
Jan 21 - Jan 22, 2026
Total with taxes and fees
Annapolis Boat Life - Overnight Stays

Vacation Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
$263 nightly
The price is $279
Dec 25 - Dec 26
Total with taxes and fees
Waterfront Getaway with Dock
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top St. Michaels Hotel Reviews

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit St. Michaels in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $1,306 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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: Visitors like this St. Michaels vacation home rental. It 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.