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Guest Houses in St. Michaels

Our top choices for St. Michaels guest houses

Sandaway Suites & Beach
Private beach, sun loungers, kayaking, fishing

Sandaway Suites & Beach

3.0 star property
9.4 out of 10, Exceptional, (152)
"Stunning property and a wonderful place to stay in Oxford. We will be back soon. "
Sandaway Suites & Beach
Island Life! Kent Island Waterfront with Pool-Bring your boat!
3 bedrooms, iron/ironing board, travel crib, free WiFi

Island Life! Kent Island Waterfront with Pool-Bring your boat!

10.0 out of 10, Exceptional, (197)
"Wonderful house with great water access. Great place to relax and visit and recreate "
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Riverview Retreat on Warehouse Creek - sleeps 6
Outdoor dining

Riverview Retreat on Warehouse Creek - sleeps 6

10.0 out of 10, Exceptional, (29)
"Very clean, quiet, they provided everything. It was beautiful and peaceful. I would love to stay there again. "
Riverview Retreat on Warehouse Creek - sleeps 6
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Fridge, microwave, oven, stovetop

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

10.0 out of 10, Exceptional, (19)
"Loved the stay here. Such a nice cute spot and so close to everything we needed."
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Calico Cottage Guest House
Terrace/patio

Calico Cottage Guest House

10.0 out of 10, Exceptional, (9)
"This tiny house is tastefully furnished and, coupled with the quiet neighborhood, provides a relaxing, peaceful environment."
Calico Cottage Guest House
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

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!

10/10 Excellent
"Beautifully restored historic home, in a quaint neighborhood, near the water and downtown. We loved it!"
Michael S. 2-night trip
Posted 1 day ago
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!