St. Michaels Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for St. Michaels holiday 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, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is HK$1,762
HK$3,561 total
includes taxes & fees
26 May - 27 May
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, (44 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 HK$1,357
HK$2,916 total
includes taxes & fees
1 Jun - 2 Jun
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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 HK$1,957
HK$3,278 total
includes taxes & fees
18 May - 19 May
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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 HK$1,762
HK$3,545 total
includes taxes & fees
19 May - 20 May
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Third-party on-site parking

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)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is HK$1,645
HK$3,404 total
includes taxes & fees
19 May - 20 May
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
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 HK$2,519
HK$4,936 total
includes taxes & fees
17 May - 18 May
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (27 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is HK$1,214
HK$1,992 total
includes taxes & fees
17 May - 18 May
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 HK$971
HK$2,266 total
includes taxes & fees
18 May - 19 May
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Marina

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 HK$1,527
HK$3,022 total
includes taxes & fees
27 May - 28 May
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
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 stay, would do it again."
United States
Brandon D.
The price is HK$1,442
HK$3,006 total
includes taxes & fees
27 May - 28 May
Charming Coastal/Country Home w/3 Acres & Sauna!
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 HK$1,582
HK$3,087 total
includes taxes & fees
2 Jun - 3 Jun
Bayside Cottage steps from Rock Hall Harbor
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 HK$994
HK$1,909 total
includes taxes & fees
18 May - 19 May
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Pool

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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 HK$1,331
HK$3,813 total
includes taxes & fees
19 May - 20 May
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Marina

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 HK$1,350
HK$3,780 total
includes taxes & fees
26 May - 27 May
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is HK$845
HK$2,775 total
includes taxes & fees
20 May - 21 May
Walk to Beach! King Bed & Free Beach Passes
Dining

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 HK$1,651
HK$4,176 total
includes taxes & fees
18 May - 19 May
Charming Pet-Friendly Stay - Near Bay & Beaches.
Property grounds

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 HK$2,387
HK$4,531 total
includes taxes & fees
17 May - 18 May
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (44 reviews)
"The place was vey clean, whic is of upmost improtance to me. We loved the veiw and the location."
United States
Crystal H.
The price is HK$3,061
HK$3,805 total
includes taxes & fees
27 May - 28 May
Sunset Breezes - quiet waterfront retreat
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (3 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is HK$1,895
HK$3,909 total
includes taxes & fees
26 May - 27 May
Sunset Cottage - West River Access and Views!
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 HK$1,801
HK$2,183 total
includes taxes & fees
2 Jun - 3 Jun
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Cortney. The Bartender was amazing."
Mario 1-night trip
Posted 2 hours ago
Crowne Plaza Annapolis by IHG

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:

  • View our selection of featured holiday rentals in St. Michaels
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Look no further and take a look at our great range of rental properties in St. Michaels!

Frequently asked questions

Are there holiday rentals in St. Michaels?

Yes, there are holiday rentals in St. Michaels close to Chesapeake Bay Maritime Museum, or you can select 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 holiday rentals that St. Michaels has to offer?

NEW! Charming Farm House in Historic Kent Island : This holiday home rental outside of St. Michaels is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in St. Michaels?

Expedia has 35 holiday 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 holiday rental in St. Michaels like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in St. Michaels. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.