Aerial panorama of shipyard and lighthouse in St. Michaels harbor in Maryland in the Chesapeake Bay

Holiday Homes in St. Michaels

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Our top choices for St. Michaels holiday homes

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (21 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is AU$726
includes taxes & fees
7 July - 8 July
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is AU$419
includes taxes & fees
15 June - 16 June
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (57 reviews)
"Great place, will stay again"
United States
Matt S.
The price is AU$397
includes taxes & fees
15 June - 16 June
Waterfront Getaway with Dock

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

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (14 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is AU$589
includes taxes & fees
19 June - 20 June
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (36 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is AU$518
includes taxes & fees
21 June - 22 June
Charming Coastal/Country Home w/3 Acres & Sauna!

Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our weekend getaway at the beautiful gated community. Great water views and a walkable community. The townhouse met all our needs. Fully stocked with essential items. The added bonus is a the workout room with top of the line equipment. A nice touch! Two great decks overlooking the marina. The owners are very responsive."
United States
Melissa
The price is AU$1,148
includes taxes & fees
15 June - 16 June
Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8

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

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (12 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is AU$912
includes taxes & fees
24 June - 25 June
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Edgewater
8.6 out of 10, Excellent, (9 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is AU$508
includes taxes & fees
14 June - 15 June
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is AU$513
includes taxes & fees
29 June - 30 June
Bayside Cottage steps from Rock Hall Harbor

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (21 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is AU$590
includes taxes & fees
24 June - 25 June
Walk to Beach! King Bed & Free Beach Passes

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
The price is AU$851
includes taxes & fees
14 June - 15 June
Charming Annapolis WaterVIEW Home

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$895
includes taxes & fees
13 July - 14 July
Annapolis Retreat - 7 mins from downtown Annapolis!

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

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (36 reviews)
"Everything was as expected, lovely spot even with lots of snow and ice!"
United States
Becky S.
The price is AU$733
includes taxes & fees
14 June - 15 June
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (7 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is AU$827
includes taxes & fees
18 June - 19 June
Renovated Bungalow | Walk to Beach | Dog-Friendly

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AU$1,020
includes taxes & fees
14 June - 15 June
Family Home on Mayo Peninsula | Deck | Sleeps 10

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
The price is AU$784
includes taxes & fees
16 June - 17 June
Sunset Cottage - West River Access and Views!

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is AU$549
includes taxes & fees
14 June - 15 June
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (44 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is AU$829
includes taxes & fees
13 July - 14 July
Sunset Breezes - quiet waterfront retreat

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (15 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AU$1,019
includes taxes & fees
15 June - 16 June
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is AU$980
includes taxes & fees
14 June - 15 June
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
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

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St. Michaels Holiday Homes information

Number of reviews
418
Accommodation
659 Holiday Homes
Lowest Price
AU$397
Highest Price
AU$1,148