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

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Our top choices for St. Michaels vacation homes

1. 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, (52 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 ¥17,482
¥46,980 total
includes taxes & fees
Aug 12 - Aug 13
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

2. 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, (15 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 ¥39,418
¥66,017 total
includes taxes & fees
Aug 10 - Aug 11
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

3. Gorgeous Creek Side Ranch-Style Estate With Dock

Gorgeous Creek Side Ranch-Style Estate With Dock
Queenstown
10.0 out of 10, Exceptional, (11 reviews)
"This home exceeded our expectation. Beautiful home and property. Everything we needed."
United States
alana k.
Gorgeous Creek Side Ranch-Style Estate With Dock

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (44 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is ¥17,482
¥46,980 total
includes taxes & fees
Aug 13 - Aug 14
Charming Coastal/Country Home w/3 Acres & Sauna!

5. 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)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is ¥60,558
¥106,858 total
includes taxes & fees
Aug 12 - Aug 13
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

6. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (2 reviews)
"Very spacious property for a family of 14. Sleeping arrangements required a bit of creativity but everything worked out! Everyone had a great time by the pool and the property was very clean. Host was responsive and helpful during the stay!"
United States
Hoi C.
The price is ¥110,211
¥200,222 total
includes taxes & fees
Aug 30 - Aug 31
Waterfront Escape with Pool Nature Lover Paradise

7. 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, (24 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 ¥44,936
¥83,064 total
includes taxes & fees
Aug 25 - Aug 26
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

8. 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)
"The perfect off-season get-away! "
United States
Pamela B.
The price is ¥52,057
¥103,967 total
includes taxes & fees
Aug 18 - Aug 19
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

9. 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)
"Lovely ! "
United States
Ellen B.
The price is ¥17,970
¥57,136 total
includes taxes & fees
Sep 1 - Sep 2
Beachside Oasis with Beach Passes & King Suite by A Haven Away

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)
"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 ¥45,481
¥86,610 total
includes taxes & fees
Sep 7 - Sep 8
Sunset Cottage - West River Access and Views!

11. Chic retreat steps to Water, Piers & Waterfront Park

Chic retreat steps to Water, Piers & Waterfront Park
Deale
10.0 out of 10, Exceptional, (1 review)
"This place is beautiful, and big. The back yard is nice. We played games out back and had a cookout. Walking distance to the pier and a playground. The"
United States
Jamie C.
Chic retreat steps to Water, Piers & Waterfront Park

12. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is ¥27,173
¥76,453 total
includes taxes & fees
Aug 10 - Aug 11
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

13. Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Pool • 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 ¥51,243
¥68,752 total
includes taxes & fees
Aug 10 - Aug 11
Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8

14. Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is ¥43,616
¥113,350 total
includes taxes & fees
Aug 9 - Aug 10
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

15. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (11 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is ¥35,973
¥94,664 total
includes taxes & fees
Aug 12 - Aug 13
Renovated Bungalow | Walk to Beach | Dog-Friendly

16. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (73 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is ¥59,426
¥116,523 total
includes taxes & fees
Sep 1 - Sep 2
Charming Annapolis WaterVIEW Home

17. 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, (37 reviews)
"Such a great house! "
United States
Stephanie V.
The price is ¥26,394
¥78,225 total
includes taxes & fees
Sep 1 - Sep 2
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

18. 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 ¥30,746
¥88,075 total
includes taxes & fees
Sep 1 - Sep 2
Annapolis Retreat - 7 mins from downtown Annapolis!

19. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (64 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is ¥36,264
¥43,955 total
includes taxes & fees
Aug 11 - Aug 12
Waterfront Getaway with Dock

20. 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 ¥45,409
¥118,811 total
includes taxes & fees
Sep 1 - Sep 2
Family Home on Mayo Peninsula | Deck | Sleeps 10
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

Find out more about St. Michaels

St. Michaels Vacation Homes information

Number of reviews
338
Accommodation
679 Vacation Homes
Lowest Price
¥43,955
Highest Price
¥200,222

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