Search Cottages in St. Michaels

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Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for St. Michaels cottages

Microwave, oven, stovetop, dishwasher
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Cottage in North Beach

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is €242
includes taxes & fees
1 Jan - 2 Jan 2026
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Cottage in Stevensville

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is €772
includes taxes & fees
22 Jan - 23 Jan 2026
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16)
"Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer."
United States
Michael C.
The price is €528
includes taxes & fees
21 Jan - 22 Jan 2026
Secluded Cozy Cottage in Historic Downtown
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

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Beautiful and perfect location"
Lauren 1-night trip
Posted 1 day ago
The Westin Annapolis

Find out more about St. Michaels

St. Michaels Cottages information

Number of reviews
19
Accommodation
98 Cottages
Lowest Price
€242
Highest Price
€772

Frequently asked questions

How much do cottages in St. Michaels cost?
Expect to pay between €242 and €772 per night for cottages in St. Michaels. No matter your budget, an excellent stay is only clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in St. Michaels?
Choose from 98 cottages in St. Michaels. No matter if you're holidaying with the family or organising a weekend escape with your besties, Expedia can help you find the right space to reconnect with nature.
Why book your cottage in St. Michaels with Expedia?
Expedia has some superb cottages in St. Michaels, so start packing for a memorable stay close to nature. If you have a budget, select how much you want to spend and the star rating of your property. Or, make use of our filters to search for cottages with a hot tub or free WiFi. We'll help you find the perfect fit whatever your plans or bank balance.
How can I find cheap cottages in St. Michaels?
A wonderful way to get cheap cottages in St. Michaels is with Expedia's user-friendly filter tool. Refine your search by budget, amenities and star rating to snag awesome prices in just a few clicks.
What is there to do in St. Michaels near my cottage?
After you've unpacked your bags and settled in, venture out and discover the cool things St. Michaels has for you to experience. St. Michaels Winery is a top attraction to add to your to-do list.

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