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Vacation Homes in St. Michaels

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
The price is ¥27,214
¥32,373 total
includes taxes & fees
Oct 21 - Oct 22
Chesapeake Bay Harbor View in a central location to events/restaurants

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

10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (15)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is ¥26,458
¥58,816 total
includes taxes & fees
Oct 20 - Oct 21
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (47)
"Property was as listed. We enjoyed are stay."
The price is ¥27,549
¥60,675 total
includes taxes & fees
Oct 13 - Oct 14
Beautiful Waterfront Retreat in Cambridge!

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!"
The price is ¥26,458
¥53,367 total
includes taxes & fees
Oct 13 - Oct 14
Bayside Cottage steps from Rock Hall Harbor

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

9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
The price is ¥37,798
¥62,342 total
includes taxes & fees
Oct 16 - Oct 17
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
The price is ¥13,494
¥40,587 total
includes taxes & fees
Oct 21 - Oct 22
Relax on Kent Island in 3 Bedroom Home w/Waterview

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

9.6 out of 10, Exceptional, (30)
"Nice and peaceful stay for a quick local getaway. "
The price is ¥12,053
¥39,383 total
includes taxes & fees
Oct 15 - Oct 16
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

10.0 out of 10, Exceptional, (6)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
The price is ¥33,518
¥72,194 total
includes taxes & fees
Oct 27 - Oct 28
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (51)
"Great location with everything you may need. It is close to restaurants and Emily’s produce.2nd time staying and will be back again. "
The price is ¥34,774
¥42,149 total
includes taxes & fees
Nov 9 - Nov 10
Waterfront Getaway 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."
The price is ¥22,039
¥61,563 total
includes taxes & fees
Oct 16 - Oct 17
Family Beach House: Spacious Deck, Grill & Views

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 ¥22,039
¥64,556 total
includes taxes & fees
Oct 12 - Oct 13
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Wright's Cottage- Pet's Welcome & EV Charging

9.0 out of 10, Wonderful, (14)
"The property was well cleaned and communication with owner was excellent. Would stay again"
The price is ¥31,510
¥62,616 total
includes taxes & fees
Oct 12 - Oct 13
Wright's Cottage- Pet's Welcome & EV Charging

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

8.8 out of 10, Excellent, (9)
"This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay."
The price is ¥52,238
¥99,765 total
includes taxes & fees
Oct 19 - Oct 20
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

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

10.0 out of 10, Exceptional, (14)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is ¥49,850
¥93,561 total
includes taxes & fees
Oct 13 - Oct 14
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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

10.0 out of 10, Exceptional, (30)
"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 ¥27,274
¥77,930 total
includes taxes & fees
Oct 20 - Oct 21
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is ¥24,182
¥78,441 total
includes taxes & fees
Nov 3 - Nov 4
Holly Hill Haven - Sleeps 10

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (5)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
The price is ¥31,537
¥80,966 total
includes taxes & fees
Oct 15 - Oct 16
Charming Pet-Friendly Stay - Near Bay & Beaches.

Cute bungalow blocks to Stadium

10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
The price is ¥26,019
¥84,833 total
includes taxes & fees
Oct 13 - Oct 14
Cute bungalow blocks to Stadium

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

10.0 out of 10, Exceptional, (10)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is ¥35,967
¥81,830 total
includes taxes & fees
Nov 4 - Nov 5
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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
311
Accommodation
694 Vacation Homes
Lowest Price
¥39,383
Highest Price
¥99,765

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