Vacation rentals in St. Michaels
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Vacation rentals in St. Michaels
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Saint Michaels MD
0.13 km from city centre
Stay at this apartment in St. Michaels. Enjoy a garden, laundry facilities, and balconies. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina are located nearby.
Kitchen
Washer
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
St Michaels MD
0.2 km from city centre
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and patios. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina are located nearby.
Pool
Kitchen
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
St Michaels MD
0.18 km from city centre
Book a stay at this family-friendly cottage in St. Michaels. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina are located nearby.
Pool
Kitchen
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
St. Michaels MD
0.11 km from city centre
Stay at this vacation home in St. Michaels. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina are located nearby.
Kitchen
Washer
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Stevensville MD
17.99 km from city centre
Book a stay at this golf vacation home in Stevensville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Matapeake State Park and Northern Chesapeake Bay are located nearby.
Kitchen
Washer
Floating 2 bed 2 bath condo stunning views of the bay
Stevensville MD
18.78 km from city centre
Stay at this houseboat in Stevensville. Enjoy a beach locale and an in-room coffeemaker. Popular attractions Matapeake State Park and Romancoke Wharf County Park are located nearby.
Kitchen
Pet-friendly
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Annapolis MD
33.61 km from city centre
Stay at this vacation home in Annapolis. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Sandy Point State Park and Bay Hills Golf Club are located nearby.
Pool
Kitchen
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Annapolis MD
31.35 km from city centre
Stay at this vacation home in Annapolis. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Ellen O. Moyer Nature Park at Back Creek and Maryland Federation of Art are located nearby.
Kitchen
Washer
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
31.65 km from city centre
Stay at this vacation home in Woolford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad National Historical Park are located nearby.
Kitchen
Washer
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Cambridge MD
26.77 km from city centre
Book a stay at this family-friendly vacation home in Cambridge. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Spocott Windmill and Ragged Island are located nearby.
Pool
Hot tub
Million Dollar View of the Chesapeake Bay
Deale MD
28.15 km from city centre
Book a stay at this family-friendly vacation home in Deale. Enjoy free WiFi, a water park, and a garden. Popular attractions Upper Yough River and Franklin Point State Park are located nearby.
Kitchen
Washer
Cass-N-Reel Luxury Houseboat
Grasonville MD
20.43 km from city centre
Stay at this houseboat in Grasonville. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chesapeake Bay Environmental Center and Paul Reed Smith Guitars are located nearby.
Kitchen
Free WiFi
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Easton MD
4.99 km from city centre
Book a stay at this beach vacation home in Easton. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Saint Michaels Village and 1879 Hooper Straight Lighthouse are located nearby.
Pool
Kitchen
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
stevensville MD
28.44 km from city centre
Book a stay at this beach vacation home in Stevensville. Enjoy free WiFi, a beach locale, and private hot tubs. Our guests praise the helpful staff in our reviews. Popular attractions Love Point State Park and Paul Reed Smith Guitars are located nearby.
Kitchen
Washer
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Annapolis MD
31.11 km from city centre
The price is CA $1,022 per night
CA $1,022
CA $1,796 total
Jan 21 - Jan 22, 2026
includes taxes & fees
Stay at this vacation home in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Maynard-Burgess House and Kunta Kinte Plaque & Alex Haley Memorial are located nearby.
Kitchen
Washer
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.
