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

Search St. Michaels Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for St. Michaels cottages

A covered porch with wooden flooring, two wicker chairs with cushions, a small table, and a potted plant.

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.
$507 nightly
The price is $560
Oct 25 - Oct 26
Total with taxes and fees
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.
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A covered patio with a table and chairs, large windows, and an American flag.

3. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
$429 nightly
The price is $474
Oct 23 - Oct 24
Total with taxes and fees
Plum Point Cottage #17
An outdoor dining area with a wooden table and chairs, a bottle of wine, and a vase of flowers.

4. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
$534 nightly
The price is $590
Oct 23 - Oct 24
Total with taxes and fees
Plum Point Cottage #15
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, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
$714 nightly
The price is $814
Nov 8 - Nov 9
Total with taxes and fees
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.
View all properties
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Very pleasant surprise! Great price for studio apartment- way better than the Marriott I just checked out of!"
Rhonda 1-night trip
Posted 1 hour ago
Sonesta ES Suites Annapolis

Find out more about St. Michaels

St. Michaels Cottages information

Number of reviews
125
Accommodation
97 Cottages
Lowest Price
$474
Highest Price
$814

Frequently asked questions

How much do cottages in St. Michaels cost?
Expect to pay between $474 and $814 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 97 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.
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.

Explore a world of travel with Expedia