Search Guest Houses in St. Michaels

    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
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 6 Guest Houses in St. Michaels with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (186)
"The place was very clean , had all the things in the home to make your stay wonderful!!!! Kitchen stocked with cooking equipment, towels for the pool, and the was owner was a great host."
Island Life! Kent Island Waterfront with Pool-Bring your boat!

Newly Renovated Guest House located in Oxford MD

9.8 out of 10, Exceptional, (20)
"We had a lovely time staying in this well situated VRBO. Everything was very clear and easy with check in/out and our stay in general. We love Oxford and know it well, and this location was well suited to visiting family. We would stay here again!"
Newly Renovated Guest House located in Oxford MD

Sandaway Suites & Beach

3.0 star property
9.2 out of 10, Wonderful, (134)
"It was a very relaxing stay!!"
The price is AED 1,088
AED 1,196 total
includes taxes & fees
28 May - 29 May
Sandaway Suites & Beach

Riverview Retreat on Warehouse Creek

10.0 out of 10, Exceptional, (22)
"Very clean, quiet, they provided everything. It was beautiful and peaceful. I would love to stay there again. "
The price is AED 771
AED 1,684 total
includes taxes & fees
9 Jun - 10 Jun
Riverview Retreat on Warehouse Creek

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

10.0 out of 10, Exceptional, (15)
"Very convenient! We really enjoyed our stay and the hosts were very accommodating! "
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

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.
Don't see what you're looking for?
See all available properties in St. Michaels
Save an average of 15% on thousands of hotels when you're signed in

Other property types in St. Michaels

Waterfront Property, kayaks, private dock, near town

9.8 out of 10, Exceptional, (150)
"Wonderful! Cranbrook is beautifully decorated, is in an amazing location and the views are spectacular!. Lots of period pieces with descriptions - great historical info. Large dining room and additional eating area, nice sitting areas, kitchen is well appointed. Stairs to bedrooms but a pullout on main level. Historic house so bedrooms are walk thru but fine with us! Room for multiple remote work stations. We’ll be back."
Waterfront Property, kayaks, private dock, near town

The heart of St Michaels awaits.

10.0 out of 10, Exceptional, (35)
"We really enjoyed our stay. Accommodations were exactly as expected and advertised. Would certainly stay here again."
The heart of St Michaels awaits.

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (37)
"Very clean, great location"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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.