Search Guest Houses in St. Michaels from CA $155

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select 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, (145)
"Beautiful historic building and rooms. Scenic, quiet grounds, calming views of the bay. A true gem !"
The price is CA $394
CA $434 total
includes taxes & fees
Aug 21 - Aug 22
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, (195)
"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, (26)
"Very clean, quiet, they provided everything. It was beautiful and peaceful. I would love to stay there again. "
The price is CA $223
CA $570 total
includes taxes & fees
Aug 26 - Aug 27
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, (23)
"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."
The price is CA $155
CA $463 total
includes taxes & fees
Aug 19 - Aug 20
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top St. Michaels Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Nice place to stay when visiting Annapolis! Cost-effective, clean, a "want to assist" staff and close to Main Street and The Dock! Could not have selected a better place for a weekend stay with friends!"
Carolynn 3-night trip
Posted 13 hours ago
Country Inn & Suites by Radisson, Annapolis, MD