A waterfront street lined with trees and a white building with a balcony.

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for St. Michaels cottages

14

1. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is AED 1,256
AED 1,967 total
includes taxes & fees
9 Nov - 10 Nov
Plum Point Cottage #14
A house with a red door, a small porch, and a view of a river with a bridge in the background.

2. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is AED 1,304
AED 1,800 total
includes taxes & fees
5 Nov - 6 Nov
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
Fire pit (2)

3. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is AED 1,252
AED 2,072 total
includes taxes & fees
4 Nov - 5 Nov
Plum Point Cottage #15
A covered patio with a table and chairs, large windows, and an American flag.

4. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AED 1,047
AED 1,662 total
includes taxes & fees
4 Nov - 5 Nov
Plum Point Cottage #17
A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

5. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (24 reviews)
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."
United States
Bridget C.
The price is AED 1,653
AED 2,496 total
includes taxes & fees
8 Nov - 9 Nov
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"The rooms were nice, the towels were nice and full. The morning breakfast was perfect enough food and nice coffee. We'll make this our go-to in Annapolis."
Jackie 1-night trip
Posted 4 hours ago
Sonesta ES Suites Annapolis

Frequently asked questions

How much do cottages in St. Michaels cost?
Expect to pay between AED 1,662 and AED 2,496 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 101 cottages in St. Michaels. No matter if you're vacationing with the family or organizing 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.

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