St. Michaels Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for St. Michaels vacation rentals

Marina

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, (21 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is ￥41,410
￥78,673 total
includes taxes & fees
Jun 2 - Jun 3
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Exterior

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, (45 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is ￥17,345
￥45,904 total
includes taxes & fees
Jun 2 - Jun 3
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina

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

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
7.8 out of 10, Good, (7 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is ￥31,058
￥61,115 total
includes taxes & fees
Jun 1 - Jun 2
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (29 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is ￥24,684
￥40,345 total
includes taxes & fees
Jun 10 - Jun 11
Sailwinds Loft at Cambridge Creek
Beach

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, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is ￥18,762
￥45,675 total
includes taxes & fees
May 31 - Jun 1
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (57 reviews)
"Great place, will stay again"
United States
Matt S.
The price is ￥36,632
￥44,232 total
includes taxes & fees
Jun 2 - Jun 3
Waterfront Getaway with Dock
Marina

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, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is ￥40,614
￥77,323 total
includes taxes & fees
Jun 3 - Jun 4
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina

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, (11 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is ￥43,003
￥80,193 total
includes taxes & fees
Jun 3 - Jun 4
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Dining

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)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
The price is ￥39,813
￥66,678 total
includes taxes & fees
Jun 1 - Jun 2
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
1 bedroom, iron/ironing board, WiFi, bed sheets

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is ￥22,935
￥41,700 total
includes taxes & fees
Jun 23 - Jun 24
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Exterior

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 response time, the place is quite, house is huge and a lot of sleeping places."
United States
Luccas C.
The price is ￥19,710
￥48,412 total
includes taxes & fees
Jun 3 - Jun 4
Charming Coastal/Country Home w/3 Acres & Sauna!
Smart TV

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 ￥49,511
￥98,402 total
includes taxes & fees
Jun 1 - Jun 2
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Smart TV

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 ￥27,872
￥57,907 total
includes taxes & fees
Jun 15 - Jun 16
Bayside Cottage steps from Rock Hall Harbor
Outdoor pool, a heated pool

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 ￥38,703
￥73,354 total
includes taxes & fees
Jun 1 - Jun 2
Waterfront Oasis of Annapolis Star
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (20 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is ￥13,715
￥52,602 total
includes taxes & fees
Jun 1 - Jun 2
Walk to Beach! King Bed & Free Beach Passes
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
The price is ￥42,860
￥93,345 total
includes taxes & fees
Jun 10 - Jun 11
Charming Annapolis WaterVIEW Home
Outdoor dining

Waterfront Unit | Dock, Kayaks & SUPs Included

Waterfront Unit | Dock, Kayaks & SUPs Included
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is ￥30,898
￥73,716 total
includes taxes & fees
May 31 - Jun 1
Waterfront Unit | Dock, Kayaks & SUPs Included
Pool

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 ￥30,580
￥81,454 total
includes taxes & fees
May 31 - Jun 1
Family Beach House: Spacious Deck, Grill & Views
Fridge, microwave, oven, stovetop

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is ￥33,287
￥78,618 total
includes taxes & fees
Jun 10 - Jun 11
Pool Loft Suite | Bay Access & Beach Passes
Beach

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Edgewater
8.6 out of 10, Excellent, (8 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is ￥35,836
￥56,286 total
includes taxes & fees
May 31 - Jun 1
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
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

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Always a great location and nice staff. Only reason I did not give a 5 star is because the coffee maker in the room did not work."
Lewis 1-night trip
Posted less than an hour ago
Historic Inns of Annapolis

Find out more about St. Michaels

Search for holiday rentals in St. Michaels on Expedia! You can easily find your home rentals, villas, holiday apartments in St. Michaels using one of the methods below:

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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?

Dollhouse in Central Historic St Michaels: Visitors like this St. Michaels vacation home rental. It offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in St. Michaels?

Expedia has 35 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.