Holiday Homes in St. Michaels

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Our top choices for St. Michaels holiday 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, (45 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 €227
includes taxes & fees
3 Jun - 4 Jun
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
9.6 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 €426
includes taxes & fees
3 Jun - 4 Jun
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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, (13 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 €364
includes taxes & fees
9 Jun - 10 Jun
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
9.6 out of 10, Exceptional, (35 reviews)
"Great response time, the place is quite, house is huge and a lot of sleeping places."
United States
Luccas C.
The price is €259
includes taxes & fees
9 Jun - 10 Jun
Charming Coastal/Country Home w/3 Acres & Sauna!

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 €237
includes taxes & fees
3 Jun - 4 Jun
Waterfront Getaway with Dock

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 €354
includes taxes & fees
15 Jun - 16 Jun
Walk to Beach! King Bed & Free Beach Passes

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.4 out of 10, Exceptional, (6 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is €489
includes taxes & fees
3 Jun - 4 Jun
Renovated Bungalow | Walk to Beach | Dog-Friendly

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"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!"
United States
Dorothy R.
The price is €307
includes taxes & fees
3 Jun - 4 Jun
Bayside Cottage steps from Rock Hall Harbor

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 €511
includes taxes & fees
10 Jun - 11 Jun
Charming Annapolis WaterVIEW Home

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 €761
includes taxes & fees
16 Jun - 17 Jun
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, (11 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 €540
includes taxes & fees
3 Jun - 4 Jun
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

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 €488
includes taxes & fees
9 Jun - 10 Jun
Annapolis Retreat - 7 mins from downtown Annapolis!

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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 €543
includes taxes & fees
9 Jun - 10 Jun
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is €327
includes taxes & fees
15 Jun - 16 Jun
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

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

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, (35 reviews)
"Everything was as expected, lovely spot even with lots of snow and ice!"
United States
Becky S.
The price is €636
includes taxes & fees
15 Jun - 16 Jun
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is €374
includes taxes & fees
9 Jun - 10 Jun
3-bedroom house in Deale located on Bay many amenities and great views

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is €455
includes taxes & fees
8 Jun - 9 Jun
Cute bungalow blocks to Stadium

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
The price is €411
includes taxes & fees
10 Jun - 11 Jun
3-Bedroom Beach Home w/ Backyard

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 €487
includes taxes & fees
16 Jun - 17 Jun
Sunset Cottage - West River Access and Views!
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 Holiday Homes information

Number of reviews
11,086
Accommodation
653 Holiday Homes
Lowest Price
€72
Highest Price
€570