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Cottages in St. Michaels

Our top choices for St. Michaels cottages

6 Mi to Dtwn: Family-friendly Home in Annapolis!
Interior

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
North Beach Cottage - Walk to Chesapeake Bay
Cottage (3 Bedrooms) | Interior

North Beach Cottage - Walk to Chesapeake Bay

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house condition was very cleran,beautiful. we appreciate the house owner's guidance&help. we made very good memories!"
North Beach Cottage - Walk to Chesapeake Bay
Waterfront North Beach Home ~ 2 Mi to Beach!
House (2 Bedrooms) | Interior

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!
Tilghman Island Retreat By Knapps Narrows!
House (2 Bedrooms) | Front of property

Tilghman Island Retreat By Knapps Narrows!

3.0 star property
Tilghman Island Retreat By Knapps Narrows!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Exterior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Cottage (2 Bedrooms) | Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very Good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Waterfront Annapolis Home: Fire Pit & Fishing Pier
House (3 Bedrooms) | Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
House (4 Bedrooms) | Interior

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

3.0 star property
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
House (4 Bedrooms) | Interior

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

3.0 star property
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Updated North Beach Cottage: Pet Friendly!
Cottage (3 Bedrooms) | Front of property

Updated North Beach Cottage: Pet Friendly!

3.0 star property
6.0 out of 10, (1)
"The property needs a severe cleaning. The floors were filthy. "
Updated North Beach Cottage: Pet Friendly!
Bayfront Gem w/ Amazing Water Views + Pond!
Front of property

Bayfront Gem w/ Amazing Water Views + Pond!

3.0 star property
Bayfront Gem w/ Amazing Water Views + Pond!
Annapolis Home Near Beach & Quiet Waters Park!
Terrace/patio

Annapolis Home Near Beach & Quiet Waters Park!

3.0 star property
Annapolis Home Near Beach & Quiet Waters Park!
Grasonville Home w/ Private Pool on the Water
House (3 Bedrooms) | Interior

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville Home w/ Private Pool on the Water
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
House (1 Bedroom) | Interior

Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit

3.0 star property
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Bayfront Maryland Retreat w/ Deck, Near Beaches!
House (3 Bedrooms) | Front of property

Bayfront Maryland Retreat w/ Deck, Near Beaches!

3.0 star property
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Beautiful Colonial Home on the Choptank River
House (4 Bedrooms) | Interior

Beautiful Colonial Home on the Choptank River

3.0 star property
Beautiful Colonial Home on the Choptank River
Waterfront Retreat < 4 Mi to Dtwn Cambridge!
House (4 Bedrooms) | Front of property

Waterfront Retreat < 4 Mi to Dtwn Cambridge!

3.0 star property
Waterfront Retreat < 4 Mi to Dtwn Cambridge!
Waterfront Home w/ Hot Tub in Bozman Village!
House (4 Bedrooms) | Interior

Waterfront Home w/ Hot Tub in Bozman Village!

3.0 star property
Waterfront Home w/ Hot Tub in Bozman Village!
Water-view Deale Home: Walk to Marina, Restaurants
House (5 Bedrooms) | Interior

Water-view Deale Home: Walk to Marina, Restaurants

3.0 star property
Water-view Deale Home: Walk to Marina, Restaurants
Waterfront Cambridge Home: Pool & Dock!
House (4 Bedrooms) | Interior

Waterfront Cambridge Home: Pool & Dock!

3.0 star property
Waterfront Cambridge Home: Pool & Dock!
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

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

10/10 Excellent
"Friendly clean and secure place "
Tina 2-night trip
Posted 2 days ago
Candlewood Suites Annapolis by IHG

Find out more about St. Michaels

Find out more about St. Michaels

St. Michaels Cottages information

Number of reviews
3
Accommodation
41 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in St. Michaels cost?
Expect to pay between and 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 41 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.

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