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
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City MarinaCambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
Traci C.
The price is CA $310
CA $626 total
includes taxes & fees
May 26 - May 27
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGECambridge
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! "
Mr.
The price is CA $454
CA $871 total
includes taxes & fees
May 27 - May 28
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Great overnight stay for a wedding nearby. Would highly recommend!"
Kevin F.
The price is CA $344
CA $581 total
includes taxes & fees
May 26 - May 27
Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great response time, the place is quite, house is huge and a lot of sleeping places."
Luccas C.
The price is CA $170
CA $439 total
includes taxes & fees
May 25 - May 26
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, (44 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
Brian
The price is CA $220
CA $497 total
includes taxes & fees
Jun 2 - Jun 3
Bayside Cottage steps from Rock Hall Harbor
Bayside Cottage steps from Rock Hall HarborRock Hall
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!"
Dorothy R.
The price is CA $241
CA $499 total
includes taxes & fees
Jun 10 - Jun 11
Waterfront Getaway with Dock
Waterfront Getaway with DockWoolford
10.0 out of 10, Exceptional, (57 reviews)
"Great place, will stay again"
Matt S.
The price is CA $317
CA $380 total
includes taxes & fees
May 27 - May 28
Sunset Breezes - quiet waterfront retreat
Sunset Breezes - quiet waterfront retreatDorchester County
10.0 out of 10, Exceptional, (44 reviews)
"Comfortable, roomy, awesome views!"
John C.
The price is CA $514
CA $642 total
includes taxes & fees
May 27 - May 28
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
Country Inn & Suites by Radisson, Annapolis, MD
8/10 Good
Find out more about St. Michaels
St. Michaels Vacation Homes information
Number of reviews | 403 |
|---|---|
Accommodation | 653 Vacation Homes |
Lowest Price | CA $380 |
Highest Price | CA $1,146 |
Explore a world of travel with Expedia
- 4 Star Hotels in Eastern Shore
- 5 Star Hotels in Eastern Shore
- Hotels near Avalon Theatre
- Apartments in Bellevue
- Condo Rentals in Bellevue
- Motels in Bellevue
- Bozman Hotels
- Lodges in Bozman
- B&B in Claiborne
- Claiborne Hotels
- B&B in Eastern Shore
- Cabin Rentals in Eastern Shore
- Condo Rentals in Eastern Shore
- Cottages in Eastern Shore
- Beach Hotel Hotels in Eastern Shore
- Luxury Hotels in Eastern Shore
- Oceanfront Hotels in Eastern Shore
- Romantic Hotels in Eastern Shore
- Spa Hotels in Eastern Shore
- Eastern Shore Hotels
- Motels in Eastern Shore
- Farmstay in Easton
- B&B in Easton
- Beach Hotel Hotels in Easton
- Boutique Hotels in Easton
- Cheap Hotels in Easton
- Luxury Hotels in Easton
- Pet-Friendly Hotels in Easton
- Spa Hotels in Easton
- Easton Hotels
- Inns in Easton
- Neavitt Hotels
- Farmstay in Oxford
- Aparthotels in Oxford
- Apartments in Oxford
- B&B in Oxford
- Beach Hotel Hotels in Oxford
- Casino Hotels in Oxford
- Family Hotels in Oxford
- Historic Hotels in Oxford
- Luxury Hotels in Oxford
- Pet-Friendly Hotels in Oxford
- Spa Hotels in Oxford
- Oxford Hotels
- B&B in Royal Oak
- Guest Houses in Royal Oak
- Cheap Hotels in Royal Oak
- Hotels & Resorts for Couples in Royal Oak
- Luxury Hotels in Royal Oak
- Spa Hotels in Royal Oak
- Hotel Wedding Venues Hotels in Royal Oak
- Royal Oak Hotels
- Inns in Royal Oak
- Lodges in Royal Oak
- Motels in Royal Oak
- Aparthotels in Sherwood
- B&B in Sherwood
- Chalets in Sherwood
- Boutique Hotels in Sherwood
- Cheap Hotels in Sherwood
- Hotels with smoking rooms in Sherwood
- Pet-Friendly Hotels in Sherwood
- Romantic Hotels in Sherwood
- Sherwood Hotels
- Inns in Sherwood
- Lodges in Sherwood
- Resorts in Sherwood
- Hotels near St. Michaels Museum
- Hotels near St. Michaels Winery
- Condo Rentals in Tilghman
- Cottages in Tilghman
- Beach Hotel Hotels in Tilghman
- Golf Hotels in Tilghman
- Lgbt Friendly Hotels in Tilghman
- Luxury Hotels in Tilghman
- Pet-Friendly Hotels in Tilghman
- Tilghman Hotels
- Wittman Hotels
- Flights to Eastern Shore
- Flights from Bozman
- Flights from Allentown (ABE) to Easton (ESN)
- Flights from Cincinnati (CVG) to Easton (ESN)
- Flights from Washington (DCA) to Easton (ESN)
- Flights from Dallas (DFW) to Easton (ESN)
- Flights from New York (JFK) to Easton (ESN)
- Flights from Los Angeles (LAX) to Easton (ESN)
- Flights from West Palm Beach (PBI) to Easton (ESN)