St. Michaels Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in St. Michaels

Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
9.8 out of 10, Exceptional, (44)
"This cottage is adorable. Great amenities and great location. We thoroughly enjoyed our time in St Michael’s."
United States
Audra B.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels
9.6 out of 10, Exceptional, (122)
"The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!"
United States
Kimberly L.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels
9.6 out of 10, Exceptional, (146)
"Perfect place to stay for a cousins reunion, Central location to all the shops and restaurants."
United States
Amh S.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels
9.6 out of 10, Exceptional, (125)
"Beautiful little cottage! Location is perfect."
United States
John B.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels
9.8 out of 10, Exceptional, (56)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
United States
Michael L.
Dollhouse in Central Historic St Michaels
Fridge, microwave, oven, stovetop
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic District
10.0 out of 10, Exceptional, (32)
"The location is fabulous. We could walk wherever we wanted to go. The room to bathroom ration was also great. We would stay here again. "
United States
Diana L.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Marina
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
Stevensville
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville
10.0 out of 10, Exceptional, (15)
"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."
United States
Tammy S.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Marina
Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

Grasonville
10.0 out of 10, Exceptional, (45)
"If you’re looking for a great view sitting on the water, with a modern look, convenient to everything, you need to stay on the Cass-and-Reel Luxury Houseboat!!"
United States
Karen B.
Cass-N-Reel Luxury Houseboat
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$2,204 total
includes taxes & fees
16 Nov - 17 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Fridge, microwave, oven, stovetop
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Historic District
9.4 out of 10, Exceptional, (18)
"The gigantic house was perfect for our quick Army-Navy Football game weekend. We hope to come back when it’s warm to take advantage of the great gathering spaces outdoors. Go Navy! Beat Army!!"
United States
Elizabeth B.
The price is HK$4,910
HK$9,025 total
includes taxes & fees
16 Nov - 17 Nov
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
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$2,397 total
includes taxes & fees
16 Nov - 17 Nov
Waterfront Getaway, Dock Your Boat & Play!
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
9.8 out of 10, Exceptional, (50)
"The house was so beautiful from top to bottom! It was incredibly well stocked on everything that we needed and we had an incredible weekend! The hosts were very responsive when needed and we can't speak higher about how wonderful this property is! We will certainly be back! "
United States
Julie S.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Exterior
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge
10.0 out of 10, Exceptional, (262)
"Our stay was great and Rob and Clarissa were very welcoming!"
United States
Allison L.
Family and Pet-Friendly, Waterfront with Pier
Outdoor pool
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge
9.8 out of 10, Exceptional, (7)
"The property was perfect for our family get together. We had a baby, toddler, preschooler, elementary and teens, moms, dads and grandparents. There was a place for everyone. Having a pack n’ play available would have been nice, but we procured one elsewhere. The property was large and felt very private, but Cambridge was just a quick drive."
United States
Jacqueline M.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge
10.0 out of 10, Exceptional, (14)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
United States
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (1)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is HK$1,749
HK$2,118 total
includes taxes & fees
16 Nov - 17 Nov
Chesapeake Bay Harbor View in a central location to events/restaurants
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford
9.6 out of 10, Exceptional, (21)
"The house was very nice, the host was very responsive! The outside was nice, only down side lots of mosquitos but that’s expected. "
United States
Elizabeth M.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge
10.0 out of 10, Exceptional, (79)
"Good stay overall"
United States
Bill C.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville
10.0 out of 10, Exceptional, (196)
"We had a great time with friends on our annual MD golf trip. Hal was great and the place was perfect for our group."
United States
Jason R.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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

10/10 Excellent
"Every aspect of my stay was excellent. The staff was exceptional."
Susan 3-night trip
Posted 1 day 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 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.