St. Michaels Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for St. Michaels vacation rentals

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is CA $241
CA $540 total
includes taxes & fees
Mar 30 - Mar 31
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD
Downtown Cambridge
10.0 out of 10, Exceptional, (7 reviews)
"The property was clean, accurate to the listing and to prior feedback from other visitors. We loved the area; very quaint and cute. We enjoyed our stay and would recommend it to anyone looking for a cozy place to stay. "
United States
Amanda S.
The price is CA $204
CA $495 total
includes taxes & fees
Mar 26 - Mar 27
Station House East: Upscale Loft in the Historic District Cambridge, MD

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (12 reviews)
"Host was personally accessible during stay, responded quickly, and went the extra mile with wonderful touches left around the place."
United States
John S.
The price is CA $241
CA $540 total
includes taxes & fees
Mar 29 - Mar 30
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Downtown Cambridge
10.0 out of 10, Exceptional, (10 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is CA $255
CA $556 total
includes taxes & fees
Mar 30 - Mar 31
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is CA $344
CA $581 total
includes taxes & fees
Mar 26 - Mar 27
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very good, (6 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is CA $193
CA $441 total
includes taxes & fees
Mar 26 - Mar 27
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
8.8 out of 10, Excellent, (10 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is CA $428
CA $850 total
includes taxes & fees
Mar 26 - Mar 27
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (24 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is CA $213
CA $347 total
includes taxes & fees
Mar 27 - Mar 28
Sailwinds Loft at Cambridge Creek

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is CA $237
CA $664 total
includes taxes & fees
Mar 26 - Mar 27
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is CA $285
CA $566 total
includes taxes & fees
Mar 26 - Mar 27
Waterfront Oasis of Annapolis Star

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is CA $162
CA $395 total
includes taxes & fees
Mar 26 - Mar 27
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is CA $179
CA $449 total
includes taxes & fees
Apr 12 - Apr 13
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is CA $165
CA $432 total
includes taxes & fees
Apr 8 - Apr 9
Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.8 out of 10, Exceptional, (12 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is CA $409
CA $842 total
includes taxes & fees
Mar 29 - Mar 30
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $234
CA $609 total
includes taxes & fees
Mar 26 - Mar 27
Family Beach House: Spacious Deck, Grill & Views

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is CA $241
CA $495 total
includes taxes & fees
Apr 13 - Apr 14
Bayside Cottage steps from Rock Hall Harbor

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is CA $365
CA $737 total
includes taxes & fees
Mar 29 - Mar 30
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (53 reviews)
"Great place, will stay again"
United States
Matt S.
The price is CA $317
CA $382 total
includes taxes & fees
Mar 26 - Mar 27
Waterfront Getaway with Dock

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (43 reviews)
"Clean, quiet, comfy"
United Kingdom
Deborah V.
The price is CA $421
CA $529 total
includes taxes & fees
Apr 12 - Apr 13
Sunset Breezes - quiet waterfront retreat

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is CA $290
CA $734 total
includes taxes & fees
Apr 5 - Apr 6
Charming Pet-Friendly Stay - Near Bay & Beaches.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top St. Michaels Hotel Reviews

Find out more about St. Michaels

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with St. Michaels. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: You might want to consider this vacation home rental near St. Michaels, which is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals are there in St. Michaels?

Expedia has 34 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.