Holiday Homes in St. Michaels

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Featured Holiday Homes in St. Michaels and around

Chesapeake Bay Harbor View in a central location to events/restaurants
Outdoor dining

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
The price is €189
includes taxes & fees
9 Oct - 10 Oct
Chesapeake Bay Harbor View in a central location to events/restaurants
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Property grounds

Adorable two-bedroom retreat close to Easton, Denton, Centreville

10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
The price is €278
includes taxes & fees
9 Oct - 10 Oct
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (15)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is €361
includes taxes & fees
9 Oct - 10 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (47)
"Property was as listed. We enjoyed are stay."
The price is €344
includes taxes & fees
12 Oct - 13 Oct
Beautiful Waterfront Retreat in Cambridge!
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is €309
includes taxes & fees
9 Oct - 10 Oct
Bayside Cottage steps from Rock Hall Harbor
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
The price is €360
includes taxes & fees
9 Oct - 10 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
The price is €246
includes taxes & fees
20 Oct - 21 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Marina

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (30)
"Nice and peaceful stay for a quick local getaway. "
The price is €231
includes taxes & fees
15 Oct - 16 Oct
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
The price is €413
includes taxes & fees
27 Oct - 28 Oct
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (51)
"Great location with everything you may need. It is close to restaurants and Emily’s produce.2nd time staying and will be back again. "
The price is €245
includes taxes & fees
12 Oct - 13 Oct
Waterfront Getaway with Dock
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Pool

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is €361
includes taxes & fees
16 Oct - 17 Oct
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Exterior

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (2)
"The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side."
The price is €368
includes taxes & fees
9 Oct - 10 Oct
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Wright's Cottage- Pet's Welcome & EV Charging
TV, offices

Wright's Cottage- Pet's Welcome & EV Charging

9.0 out of 10, Wonderful, (14)
"The property was well cleaned and communication with owner was excellent. Would stay again"
The price is €358
includes taxes & fees
12 Oct - 13 Oct
Wright's Cottage- Pet's Welcome & EV Charging
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Interior

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

8.8 out of 10, Excellent, (9)
"This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay."
The price is €579
includes taxes & fees
21 Oct - 22 Oct
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

10.0 out of 10, Exceptional, (14)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is €522
includes taxes & fees
21 Oct - 22 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach nearby, sun-loungers, beach towels

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (30)
"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "
The price is €444
includes taxes & fees
3 Nov - 4 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Holly Hill Haven - Sleeps 10
TV, books, offices

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is €457
includes taxes & fees
3 Nov - 4 Nov
Holly Hill Haven - Sleeps 10
Charming Pet-Friendly Stay - Near Bay & Beaches.
Interior

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (5)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
The price is €545
includes taxes & fees
9 Oct - 10 Oct
Charming Pet-Friendly Stay - Near Bay & Beaches.
Cute bungalow blocks to Stadium
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
The price is €487
includes taxes & fees
13 Oct - 14 Oct
Cute bungalow blocks to Stadium
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Terrace/patio

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

10.0 out of 10, Exceptional, (10)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is €448
includes taxes & fees
15 Oct - 16 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful hotel in the heart of Annapolis. Lots of charm "
Sara 1-night trip
Posted 5 days ago
Historic Inns of Annapolis

Find out more about St. Michaels

Find out more about St. Michaels

St. Michaels Holiday Homes information

Number of reviews
308
Accommodation
723 Holiday Homes
Lowest Price
€231
Highest Price
€579

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