Photo by Lin R

St. Michaels Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Jan - 14 Jan
Tomorrow
14 Jan - 15 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for St. Michaels holiday rentals

Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Holiday Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (17 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$549
HK$2,416 total
includes taxes & fees
15 Jan - 16 Jan
Walk to Beach! King Bed & Free Beach Passes
Marina
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Condo in Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
9.8 out of 10, Exceptional, (11 reviews)
"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$1,092
HK$2,671 total
includes taxes & fees
9 Feb - 10 Feb
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Interior
Upscale Condo in Annapolis

Condo in Historic District

Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (2 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is HK$1,465
HK$3,741 total
includes taxes & fees
22 Jan - 23 Jan
Upscale Condo in Annapolis
Exterior
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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$632
HK$2,041 total
includes taxes & fees
19 Jan - 20 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City 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 clean, and very comfortable beds."
United States
Edward R.
The price is HK$1,131
HK$2,752 total
includes taxes & fees
26 Jan - 27 Jan
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Condo in Downtown Cambridge

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
2.5 star property
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$1,131
HK$2,752 total
includes taxes & fees
2 Feb - 3 Feb
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Exterior
Charming Coastal/Country Home w/3 Acres & Sauna!

Holiday Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (32 reviews)
"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$716
HK$2,122 total
includes taxes & fees
18 Jan - 19 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD

Condo in Downtown Cambridge

Station House East: Upscale Loft in the Historic District Cambridge, MD
10.0 out of 10, Exceptional, (7 reviews)
"Location very convenient, flat beautiful, clean, very friendly, respo sive and accommodating hostess! Thank you!"
United States
Solveig S.
The price is HK$1,158
HK$2,781 total
includes taxes & fees
16 Jan - 17 Jan
Station House East: Upscale Loft in the Historic District Cambridge, MD
Exterior detail
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Cottage in North Beach

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
9.6 out of 10, Exceptional, (4 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is HK$1,123
HK$2,306 total
includes taxes & fees
15 Jan - 16 Jan
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Outdoor dining
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Holiday Home in North Beach

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$909
HK$3,346 total
includes taxes & fees
21 Jan - 22 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Private kitchen
Sailwinds Loft at Cambridge Creek

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24 reviews)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is HK$1,208
HK$1,983 total
includes taxes & fees
15 Jan - 16 Jan
Sailwinds Loft at Cambridge Creek
Marina
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Houseboat in Edgewater

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
The price is HK$16,841
HK$24,362 total
includes taxes & fees
15 Jan - 16 Jan
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!

Holiday Home in Cambridge

Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (50 reviews)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is HK$1,228
HK$2,905 total
includes taxes & fees
18 Jan - 19 Jan
Beautiful Waterfront Retreat in Cambridge!
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

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$936
HK$2,215 total
includes taxes & fees
15 Jan - 16 Jan
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment in Rock Hall

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (17 reviews)
"Clean, comfortable and convenient! "
United States
Jill J.
The price is HK$918
HK$2,211 total
includes taxes & fees
15 Jan - 16 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
TV, books, offices
Holly Hill Haven - Sleeps 10

Holiday Home in Edgewater

Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,154
HK$4,364 total
includes taxes & fees
3 Feb - 4 Feb
Holly Hill Haven - Sleeps 10
Fridge, microwave, dishwasher, coffee/tea maker
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Holiday Home in Centreville

HGTV quality, private guest suite, country getaway with hot tub & fire pit
10.0 out of 10, Exceptional, (8 reviews)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is HK$1,537
HK$3,480 total
includes taxes & fees
20 Jan - 21 Jan
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Interior
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Holiday Home in Historic District

Historic Row Home | Hot Tub - 1 Block from Gate 1!
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is HK$1,240
HK$5,768 total
includes taxes & fees
19 Jan - 20 Jan
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Holiday Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is HK$1,333
HK$4,322 total
includes taxes & fees
15 Jan - 16 Jan
Cute bungalow blocks to Stadium
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

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$1,614
HK$3,226 total
includes taxes & fees
15 Jan - 16 Jan
Waterfront Oasis of Annapolis Star
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top St. Michaels Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"H"
William 2-night trip
Posted 6 days 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:

  • View our selection of featured holiday rentals in St. Michaels
  • Use the map to find apartments and other holiday homes in the St. Michaels neighbourhood you prefer
  • 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?

St. Michaels Escape | Pool, Hot Tub & Fire Pit: This highly rated holiday home rental in St. Michaels is located on a river, and has a fireplace, a balcony 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.