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Vacation Homes in St. Michaels

Our top choices for St. Michaels vacation homes

Adorable two-bedroom retreat close to Easton, Denton, Centreville

10.0 out of 10, Exceptional, (26)
"This home was perfect for a quiet getaway. Relaxing to come back to after a busy day out."
Adorable two-bedroom retreat close to Easton, Denton, Centreville

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

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is SAR 938
SAR 1,571 total
includes taxes & fees
25 Aug - 26 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (49)
"Fit all of our needs. Clean,well furnished, nice kitchen. Stayed there twice and will probably go back."
The price is SAR 863
SAR 1,046 total
includes taxes & fees
25 Aug - 26 Aug
Waterfront Getaway with Dock

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

The price is SAR 811
SAR 1,275 total
includes taxes & fees
25 Aug - 26 Aug
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is SAR 676
SAR 1,476 total
includes taxes & fees
26 Aug - 27 Aug
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is SAR 390
SAR 1,145 total
includes taxes & fees
27 Aug - 28 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview

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

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is SAR 335
SAR 1,079 total
includes taxes & fees
24 Aug - 25 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Beach Home with King Bed and Beach Passes in a Cute Town

10.0 out of 10, Exceptional, (16)
"Excellent"
The price is SAR 308
SAR 1,227 total
includes taxes & fees
24 Aug - 25 Aug
Beach Home with King Bed and Beach Passes in a Cute Town

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

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is SAR 692
SAR 1,743 total
includes taxes & fees
25 Aug - 26 Aug
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is SAR 811
SAR 1,788 total
includes taxes & fees
3 Sep - 4 Sep
The Cottage

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
Cozy Home in Beautiful Annapolis

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (3)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
Charming Pet-Friendly Stay - Near Bay & Beaches.

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
The price is SAR 983
SAR 3,304 total
includes taxes & fees
23 Aug - 24 Aug
Gorgeous Creek Side Ranch-Style Estate With Dock

Family Beach House: Spacious Deck, Grill & Views

9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
Family Beach House: Spacious Deck, Grill & Views

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (44)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
The price is SAR 868
SAR 1,724 total
includes taxes & fees
27 Aug - 28 Aug
Beautiful Waterfront Retreat in Cambridge!

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is SAR 676
SAR 2,039 total
includes taxes & fees
23 Aug - 24 Aug
Holly Hill Haven - Sleeps 10

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is SAR 740
SAR 1,683 total
includes taxes & fees
25 Aug - 26 Aug
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"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!"
Bayside Cottage steps from Rock Hall Harbor

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is SAR 559
SAR 1,421 total
includes taxes & fees
26 Aug - 27 Aug
Waterfront Getaway, Dock Your Boat & Play!

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

10.0 out of 10, Exceptional, (28)
"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "
The price is SAR 777
SAR 2,047 total
includes taxes & fees
24 Aug - 25 Aug
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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