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

St. Michaels Vacation Rentals

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Our top choices for St. Michaels vacation 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 CA $391
CA $728 total
includes taxes & fees
Jul 7 - Jul 8
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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 CA $321
CA $389 total
includes taxes & fees
Jun 15 - Jun 16
Waterfront Getaway with Dock

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 CA $269
CA $561 total
includes taxes & fees
Jun 21 - Jun 22
Charming Coastal/Country Home w/3 Acres & Sauna!

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 CA $164
CA $453 total
includes taxes & fees
Jun 15 - Jun 16
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 CA $349
CA $589 total
includes taxes & fees
Jun 11 - Jun 12
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 CA $474
CA $911 total
includes taxes & fees
Jun 16 - Jun 17
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

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 CA $557
CA $1,143 total
includes taxes & fees
Jun 24 - Jun 25
Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8

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 CA $253
CA $514 total
includes taxes & fees
Jun 29 - Jun 30
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, (23 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is CA $126
CA $468 total
includes taxes & fees
Jun 14 - Jun 15
Walk to Beach! King Bed & Free Beach Passes

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 CA $314
CA $501 total
includes taxes & fees
Jun 11 - Jun 12
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

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 CA $337
CA $783 total
includes taxes & fees
Jun 11 - Jun 12
Charming Annapolis WaterVIEW Home

Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
4.0 out of 10, (1 review)
"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "
United States
rebekah h.
The price is CA $368
CA $1,007 total
includes taxes & fees
Jun 11 - Jun 12
Londontowne Rancher | 3BR | Near Waterfront

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $389
CA $877 total
includes taxes & fees
Jun 30 - Jul 1
Family Beach House: Spacious Deck, Grill & Views

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 CA $370
CA $918 total
includes taxes & fees
Jun 15 - Jun 16
Annapolis Retreat - 7 mins from downtown Annapolis!

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 CA $303
CA $826 total
includes taxes & fees
Jun 18 - Jun 19
Renovated Bungalow | Walk to Beach | Dog-Friendly

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 CA $260
CA $729 total
includes taxes & fees
Jun 11 - Jun 12
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (15 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is CA $452
CA $850 total
includes taxes & fees
Jun 17 - Jun 18
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is CA $420
CA $542 total
includes taxes & fees
Jun 14 - Jun 15
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is CA $402
CA $775 total
includes taxes & fees
Jun 16 - Jun 17
Sunset Cottage - West River Access and Views!

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 CA $698
CA $879 total
includes taxes & fees
Jun 25 - Jun 26
Sunset Breezes - quiet waterfront retreat
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 Vacation Homes information

Number of reviews
397
Accommodation
654 Vacation Homes
Lowest Price
CA $389
Highest Price
CA $1,143

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