St. Michaels Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for St. Michaels holiday rentals

Marina

Holiday Home in Cambridge

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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$1,174
HK$2,820 total
includes taxes & fees
2 Mar - 3 Mar
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Condo in Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic 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 HK$1,115
HK$2,741 total
includes taxes & fees
4 Mar - 5 Mar
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina

Condo in Downtown Cambridge

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
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$978
HK$2,272 total
includes taxes & fees
3 Mar - 4 Mar
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Marina

Condo in Downtown Cambridge

Station House East: Upscale Loft in the Historic District Cambridge, MD
10.0 out of 10, Exceptional, (7 reviews)
"The apartment was exceptionally clean and comfortable."
United States
Beth T.
The price is HK$1,162
HK$2,799 total
includes taxes & fees
2 Mar - 3 Mar
Station House East: Upscale Loft in the Historic District Cambridge, MD
Marina

Condo in Downtown Cambridge

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
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 HK$1,369
HK$3,052 total
includes taxes & fees
17 Mar - 18 Mar
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Dining

Holiday Home in Grasonville

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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 HK$1,956
HK$3,292 total
includes taxes & fees
2 Mar - 3 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Private kitchen

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is HK$1,213
HK$1,990 total
includes taxes & fees
3 Mar - 4 Mar
Sailwinds Loft at Cambridge Creek
Smart TV

Holiday Home in Cambridge

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF 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$2,432
HK$4,833 total
includes taxes & fees
2 Mar - 3 Mar
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Exterior

Holiday Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (33 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is HK$554
HK$1,964 total
includes taxes & fees
4 Mar - 5 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!
Outdoor pool, a heated pool

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,619
HK$3,237 total
includes taxes & fees
2 Mar - 3 Mar
Waterfront Oasis of Annapolis Star
Exterior

Holiday Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is HK$469
HK$1,816 total
includes taxes & fees
2 Mar - 3 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina

Holiday Home in Annapolis

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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$1,348
HK$3,793 total
includes taxes & fees
2 Mar - 3 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Beach

Apartment in Rock Hall

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is HK$922
HK$2,235 total
includes taxes & fees
2 Mar - 3 Mar
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach nearby

Holiday Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (19 reviews)
"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.
The price is HK$529
HK$2,398 total
includes taxes & fees
3 Mar - 4 Mar
Walk to Beach! King Bed & Free Beach Passes
Fridge, microwave, oven, stovetop

Holiday Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is HK$1,166
HK$4,122 total
includes taxes & fees
2 Mar - 3 Mar
Cute bungalow blocks to Stadium
TV, offices

Holiday Home in Annapolis

Wright's Cottage- Pet's Welcome & EV Charging
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is HK$1,293
HK$2,794 total
includes taxes & fees
9 Mar - 10 Mar
Wright's Cottage- Pet's Welcome & EV Charging
Fridge, microwave, oven, stovetop

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (53 reviews)
"Great place, will stay again"
United States
Matt S.
The price is HK$1,799
HK$2,131 total
includes taxes & fees
2 Mar - 3 Mar
Waterfront Getaway with Dock
Pool

Holiday Home in Chesapeak beach

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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$1,330
HK$3,431 total
includes taxes & fees
18 Mar - 19 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Smart TV

Holiday Home in Rock Hall

Bayside Cottage steps from Rock Hall Harbor
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$1,494
HK$2,944 total
includes taxes & fees
1 Apr - 2 Apr
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop

Holiday Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
The price is HK$1,174
HK$4,415 total
includes taxes & fees
2 Mar - 3 Mar
Neptune by the Water - Pet Friendly Fenced Yard
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Perfect location, comfortable bed, clean and spacious room, cheap parking around the corner that was recommended by the staff. "
Erika 2-night trip
Posted 2 days ago
Hilton Garden Inn Annapolis Downtown

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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  • Enter your travel dates to view the best deals on holiday rentals in St. Michaels while they last

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?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This holiday home rental outside of St. Michaels is located on the waterfront, and has an outdoor pool, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals are there in St. Michaels?

Expedia has 34 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.