
St. Michaels Vacation Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for St. Michaels vacation homes

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach AccessShady Side
The price is CA $223
CA $499 total
includes taxes & fees
Jul 20 - Jul 21

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven Peaceful, Spacious, 3 Bedroom RetreatRose Haven
The price is CA $388
CA $995 total
includes taxes & fees
Jul 19 - Jul 20
The price is CA $382
CA $648 total
includes taxes & fees
Jul 19 - Jul 20

Chapel Gate 3BR Steps to City Dock & Naval Academy
Chapel Gate 3BR Steps to City Dock & Naval AcademyHistoric District
The price is CA $303
CA $756 total
includes taxes & fees
Aug 10 - Aug 11
The price is CA $275
CA $815 total
includes taxes & fees
Jul 21 - Jul 22

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Annapolis Gem- Tranquil 4 BR Murray Hill VictorianHistoric District
10.0 out of 10, Exceptional, (1 review)
The price is CA $439
CA $1,112 total
includes taxes & fees
Jul 20 - Jul 21

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, (47 reviews)
The price is CA $164
CA $443 total
includes taxes & fees
Jul 22 - Jul 23

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Cozy 3BR Annapolis sleeps 6 Private Deck, ParkingAnnapolis
The price is CA $346
CA $880 total
includes taxes & fees
Aug 17 - Aug 18
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.
Find vacation rentals that suit your style
Cottages
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top St. Michaels Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection
10/10 Excellent
Find out more about St. Michaels
St. Michaels Vacation Homes information
Number of reviews | |
|---|---|
Accommodation | Vacation Homes |
Lowest Price | |
Highest Price |
Explore a world of travel with Expedia
- Vacation Homes in Kent Island
- Wades Point Inn
- Highland Beach Hotels
- Cambridge Hotels
- Condo Rentals in Edgewater
- Robert Morris Inn
- Houseboats in Queenstown
- Cabin Rentals in Woolford
- Apartments in Edgewater
- Queenstown Waterfront
- Motels in Royal Oak
- Hotels with Waterslides in Cambridge
- Cottages in Harwood
- Maryland Hotels
- Minutes from Downtown St. Michaels
- B&B in Maryland
- Washington Hotels
- Baltimore Hotels
- Waterfront Bliss: Ultimate Tilghman Retreat 4 Bedroom Home by RedAwning
- Cottages in Maryland
- Lowes Wharf Marina Inn
- Houseboats in Churchton
- Oxford Hotels
- Apartments in Maryland
- Motels in Secretary
- Hilton Hotels in Eastern Shore
- Kent Island Resort
- St. Michaels Hotels
- Marriott Hotels & Resorts in St. Michaels
- Queenstown Hotels
- Hotels with an Indoor Pool in Kent Narrows
- Easton Hotels
- Hyatt Hotels in St. Michaels
- Cabin Rentals in Churchton
- Rv Parks in Maryland
- Grasonville Hotels
- Cabin Rentals in Newcomb
- Condo Rentals in Annapolis
- B&B in Royal Oak
- Lgbt Friendly Hotels in Tilghman
- Beach Hotel Hotels in Tilghman
- B&B in Preston
- Lodges in Woolford
- Cass
- Annapolis Hotels
- Motels in Maryland
- Apartments in Oxford
- Stevensville Hotels
- Vacation Homes in Odyssey
- Cabin Rentals in Maryland
- 4 Star Hotels in Algonquin
- Adults Only Resorts & in Eastern Shore
- B&B in Woolford
- Cabin Rentals in Eastern Shore
- Cottages in Linkwood
- Pet-Friendly Hotels in Kent Island
- Oceanfront Hotels in Eastern Shore
- Arundel on the Bay Hotels
- Hotels near Avalon Theatre
- Chalets in Centreville
- Cottages in Tilghman
- Motels in Eastern Shore
- Minutes from Downtown St. Michaels
- Condo Rentals in Maryland
- Flights from Allentown (ABE) to Easton (ESN)
- Flights from Montreal (YUL) to Baltimore (BWI)
- Flights from Vancouver (YVR) to Baltimore (BWI)
- Flights to St. Michaels
- Flights from Toronto (YYZ) to Baltimore (BWI)
- Flights from Washington (DCA) to Easton (ESN)
- Flights to Maryland
- Flights from Calgary (YYC) to Baltimore (BWI)
- Flights to Eastern Shore
- Flights from Buffalo (BUF) to Baltimore (BWI)
- Flights to Baltimore
- Flights from Cincinnati (CVG) to Easton (ESN)
- Flights from Winnipeg (YWG) to Baltimore (BWI)
- Flights to Kent Island
- Flights from Edmonton (YEG) to Baltimore (BWI)
- Flights to Washington
- Flights from Los Angeles (LAX) to Easton (ESN)

















































































