Search Guest Houses in St. Michaels

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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Guest Houses in St. Michaels

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

Sandaway Suites & Beach

3.0 star property
9.4 out of 10, Exceptional, (144)
"Beautiful historic building and rooms. Scenic, quiet grounds, calming views of the bay. A true gem !"
$244 nightly
The price is $269
Aug 12 - Aug 13
Total includes taxes and fees
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, (194)
"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
TV, fireplace, offices

Riverview Retreat on Warehouse Creek - sleeps 6

10.0 out of 10, Exceptional, (25)
"Very clean, quiet, they provided everything. It was beautiful and peaceful. I would love to stay there again. "
$399 nightly
The price is $431
Aug 26 - Aug 27
Total includes taxes and fees
Riverview Retreat on Warehouse Creek - sleeps 6
Newly Renovated Guest House located in Oxford MD
Fridge, microwave, oven, stovetop

Newly Renovated Guest House located in Oxford MD

9.8 out of 10, Exceptional, (22)
"Clean and somewhat comfortable. "
Newly Renovated Guest House located in Oxford MD
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, (18)
"Loved the stay here. Such a nice cute spot and so close to everything we needed."
$278 nightly
The price is $317
Aug 6 - Aug 7
Total includes taxes and fees
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, (8)
"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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Great visit "
Chris 6-night trip
Posted 19 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What is the nightly rate for a guest house in St. Michaels?
Rates for St. Michaels guest houses vary, but travelers can find great-value prices from $269 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at St. Michaels guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a St. Michaels guest house and a B&B?
A guest house in St. Michaels is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.