St. Michaels Holiday Rentals

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Check prices for these dates

Tonight
12 Nov - 13 Nov
Tomorrow
13 Nov - 14 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Holiday Rentals in St. Michaels

Marina
#2 Egret Cottage Harris Cove

#2 Egret Cottage Harris Cove

Saint Michaels
10.0 out of 10, Exceptional, (1)
The price is HK$2,021
HK$2,982 total
includes taxes & fees
20 Nov - 21 Nov
#2 Egret Cottage Harris Cove
Property grounds
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Edgewater
The price is HK$16,787
HK$23,523 total
includes taxes & fees
13 Nov - 14 Nov
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!

Waterfront Getaway, Dock Your Boat & Play!

Edgewater
10.0 out of 10, Exceptional, (3)
"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 HK$769
HK$2,388 total
includes taxes & fees
13 Nov - 14 Nov
Waterfront Getaway, Dock Your Boat & Play!
Fridge, microwave, oven, stovetop
Annapolis Boat Life - Overnight Stays

Annapolis Boat Life - Overnight Stays

ANNAPOLIS
10.0 out of 10, Exceptional, (1)
"Great stay, host was super amazing and we had the best time!!"
United States
Kirstyn I.
The price is HK$1,404
HK$1,816 total
includes taxes & fees
3 Dec - 4 Dec
Annapolis Boat Life - Overnight Stays
Terrace/patio
Historic Downtown Luxury • USNA • Waterfront

Historic Downtown Luxury • USNA • Waterfront

Historic District
The price is HK$2,782
HK$6,158 total
includes taxes & fees
13 Nov - 14 Nov
Historic Downtown Luxury • USNA • Waterfront
Marina
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

Stevensville
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
The price is HK$530
HK$1,930 total
includes taxes & fees
13 Nov - 14 Nov
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Marina
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
Downtown Cambridge
9.6 out of 10, Exceptional, (10)
"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.
The price is HK$1,049
HK$2,677 total
includes taxes & fees
18 Nov - 19 Nov
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

2.0 star property
North Beach
10.0 out of 10, Exceptional, (1)
"Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! "
United States
Georgina P.
The price is HK$995
HK$2,150 total
includes taxes & fees
14 Nov - 15 Nov
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
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, (19)
"Great well-furnished townhouse in a great location and a super responsive host. What’s not to like?!?!"
United States
Lynn
The price is HK$1,127
HK$2,743 total
includes taxes & fees
8 Dec - 9 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is HK$612
HK$2,041 total
includes taxes & fees
17 Nov - 18 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
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, (16)
"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$823
HK$2,745 total
includes taxes & fees
1 Dec - 2 Dec
Walk to Beach! King Bed & Free Beach Passes
Interior
Upscale Condo in Annapolis

Upscale Condo in Annapolis

Historic District
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.
The price is HK$2,223
HK$4,722 total
includes taxes & fees
26 Nov - 27 Nov
Upscale Condo in Annapolis
Interior
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Wonderful stay. The Crab Shack and dock were the highlights. We spent most of our time there. It was awesome. Highly recommend. "
United States
Christopher D.
The price is HK$1,399
HK$3,106 total
includes taxes & fees
16 Nov - 17 Nov
Beautiful Waterfront Retreat in Cambridge!
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, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is HK$916
HK$2,212 total
includes taxes & fees
13 Nov - 14 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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, (2)
"The apartment was exceptionally clean and comfortable."
United States
Beth T.
The price is HK$420
HK$1,920 total
includes taxes & fees
17 Nov - 18 Nov
Station House East: Upscale Loft in the Historic District Cambridge, MD
Private kitchen
Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek

Cambridge
9.8 out of 10, Exceptional, (19)
"The location and apartment were perfect. "
United States
Christina B.
The price is HK$1,205
HK$1,977 total
includes taxes & fees
7 Dec - 8 Dec
Sailwinds Loft at Cambridge Creek
Marina
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

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

2.5 star property
Downtown Cambridge
10.0 out of 10, Exceptional, (10)
"Property was located in heart of Cambridge restaurant district. Easy access to great restaurants. Parking easy and plentiful. Condo was as beautiful as advertised! Stunning penthouse 2 bedroom apartment!"
United States
Robert
The price is HK$1,127
HK$2,776 total
includes taxes & fees
18 Nov - 19 Nov
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

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

Downtown Cambridge
8.8 out of 10, Excellent, (5)
"Should provide assigned parking space. The location is not near the water or close to the water compared to the photo you see when booking. "
United States
Felicia
The price is HK$894
HK$2,266 total
includes taxes & fees
18 Nov - 19 Nov
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,788
HK$3,447 total
includes taxes & fees
1 Dec - 2 Dec
Waterfront Oasis of Annapolis Star
Beach nearby, sun-loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach
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.
The price is HK$1,267
HK$3,786 total
includes taxes & fees
3 Dec - 4 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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
"Great location. Every employee was so friendly and seemed happy to be there. Room was clean. Everything in the room was in good, working order. "
Courtney 2-night trip
Posted 4 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:

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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?

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife: This highly rated holiday home rental in St. Michaels offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable 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 33 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.