Holiday Homes in St. Michaels

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Featured Holiday Homes in St. Michaels and around

Our top choices for St. Michaels holiday homes

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

9.6 out of 10, Exceptional, (30)
"Nice and peaceful stay for a quick local getaway. "
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (12)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is €332
includes taxes & fees
27 Aug - 28 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 €255
includes taxes & fees
27 Aug - 28 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview

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

10.0 out of 10, Exceptional, (16)
"Excellent"
Beach Home with King Bed and Beach Passes in a Cute Town

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!"
The price is €444
includes taxes & fees
25 Aug - 26 Aug
Charming Pet-Friendly Stay - Near Bay & Beaches.

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The Cottage

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 €417
includes taxes & fees
16 Sept - 17 Sept
Beautiful Waterfront Retreat in Cambridge!

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 €393
includes taxes & fees
25 Aug - 26 Aug
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is €787
includes taxes & fees
6 Sept - 7 Sept
Holly Hill Haven - Sleeps 10

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

9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is €359
includes taxes & fees
15 Sept - 16 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

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 €366
includes taxes & fees
3 Sept - 4 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 €779
includes taxes & fees
6 Sept - 7 Sept
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

8.6 out of 10, Excellent, (8)
"Spacious, orderly interior, lovely setting, great amenities: kayaks, fire pit, creek feeds into Chop tank, close to Saint Michaels and Secretary.Big bedrooms with new comfy beds, plenty of bathrooms and showers.Just a lovely place and excellent communication from host."
The price is €586
includes taxes & fees
25 Aug - 26 Aug
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (21)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
Edgewater/Mayo Gateaway w/ Hot Tub

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 €244
includes taxes & fees
25 Aug - 26 Aug
Waterfront Getaway with Dock

Neptune by the Water - Pet Friendly Fenced Yard

9.6 out of 10, Exceptional, (10)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is €476
includes taxes & fees
26 Aug - 27 Aug
Neptune by the Water - Pet Friendly Fenced Yard

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

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

10.0 out of 10, Exceptional, (13)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is €570
includes taxes & fees
25 Aug - 26 Aug
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (2)
"The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side."
The price is €468
includes taxes & fees
6 Sept - 7 Sept
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
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