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

St. Michaels Vacation Rentals

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Our top choices for St. Michaels vacation homes

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, (47 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 $122
CA $390 total
includes taxes & fees
Jul 8 - Jul 9
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (23 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is CA $376
CA $714 total
includes taxes & fees
Jul 28 - Jul 29
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (38 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 $163
CA $442 total
includes taxes & fees
Jul 9 - Jul 10
Charming Coastal/Country Home w/3 Acres & Sauna!

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (8 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is CA $376
CA $930 total
includes taxes & fees
Aug 4 - Aug 5
Renovated Bungalow | Walk to Beach | Dog-Friendly

Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is CA $183
CA $547 total
includes taxes & fees
Jul 12 - Jul 13
Beachside Oasis with Beach Passes & King Suite by A Haven Away

Annapolis Garden Suite

Annapolis Garden Suite
Epping Forest
10.0 out of 10, Exceptional, (17 reviews)
"We had a quick overnight stay to attend an event at the Naval Academy! This was the perfect spot!! The accommodations were exactly what we needed!! Thanks for a great stay!!! "
United States
Mary S.
Annapolis Garden Suite

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 $251
CA $519 total
includes taxes & fees
Jul 14 - Jul 15
Bayside Cottage steps from Rock Hall Harbor

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
The price is CA $116
CA $366 total
includes taxes & fees
Jul 14 - Jul 15
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home for a girls weekend away. The view is spectacular, host was communicative, and lots of thoughtful small touches throughout the home and the experience. Thank you for a wonderful stay! "
United States
Katie K.
The price is CA $462
CA $851 total
includes taxes & fees
Jul 8 - Jul 9
Sunset Cottage - West River Access and Views!

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (61 reviews)
"Great place, will stay again"
United States
Matt S.
The price is CA $327
CA $396 total
includes taxes & fees
Jul 15 - Jul 16
Waterfront Getaway with Dock

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is CA $344
CA $985 total
includes taxes & fees
Jul 8 - Jul 9
Family Home on Mayo Peninsula | Deck | Sleeps 10

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is CA $427
CA $555 total
includes taxes & fees
Jul 8 - Jul 9
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

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, (13 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 $686
CA $1,155 total
includes taxes & fees
Jul 29 - Jul 30
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is CA $294
CA $754 total
includes taxes & fees
Jul 20 - Jul 21
Cute bungalow blocks to Stadium

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $396
CA $892 total
includes taxes & fees
Jul 28 - Jul 29
Family Beach House: Spacious Deck, Grill & Views

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is CA $278
CA $822 total
includes taxes & fees
Jul 13 - Jul 14
Historic Row Home in Downtown Annapolis

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $387
CA $656 total
includes taxes & fees
Jul 15 - Jul 16
Plum Point Cottage #17

Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
10.0 out of 10, Exceptional, (2 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is CA $344
CA $1,049 total
includes taxes & fees
Jul 9 - Jul 10
Londontowne Home | Beach | 3BR

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, (16 reviews)
"Very nice property with plenty of room and a nice outdoor space. The hot tub was a great bonus. Close enough to visit USNA but the location feels like a vacation spot!"
United States
Gail S.
The price is CA $505
CA $982 total
includes taxes & fees
Jul 13 - Jul 14
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 $355
CA $903 total
includes taxes & fees
Jul 22 - Jul 23
Annapolis Retreat - 7 mins from downtown Annapolis!
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
267
Accommodation
679 Vacation Homes
Lowest Price
CA $366
Highest Price
CA $1,155

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