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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for St. Michaels vacation homes

Marina

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, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is ￥31,728
￥66,423 total
includes taxes & fees
Apr 20 - Apr 21
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Dining

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, (12 reviews)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
The price is ￥39,660
￥66,423 total
includes taxes & fees
Apr 20 - Apr 21
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Smart TV

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
8.8 out of 10, Excellent, (10 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 ￥49,629
￥98,346 total
includes taxes & fees
Apr 20 - Apr 21
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Marina

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 ￥27,340
￥76,923 total
includes taxes & fees
Apr 20 - Apr 21
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Exterior

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 stay, would do it again."
United States
Brandon D.
The price is ￥10,894
￥39,126 total
includes taxes & fees
Apr 20 - Apr 21
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

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, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is ￥9,182
￥36,470 total
includes taxes & fees
Apr 20 - Apr 21
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Pool

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
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 ￥26,969
￥69,567 total
includes taxes & fees
Apr 20 - Apr 21
Family Beach House: Spacious Deck, Grill & Views
Property grounds

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

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (28 reviews)
"Quiet, quaint....perfect"
United States
Catherine M.
The price is ￥29,190
￥55,829 total
includes taxes & fees
May 10 - May 11
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Smart TV

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 ￥27,762
￥57,678 total
includes taxes & fees
May 4 - May 5
Bayside Cottage steps from Rock Hall Harbor
Smart TV

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, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is ￥41,619
￥83,801 total
includes taxes & fees
Apr 20 - Apr 21
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is ￥11,931
￥49,632 total
includes taxes & fees
Apr 20 - Apr 21
Walk to Beach! King Bed & Free Beach Passes
Fridge, microwave, oven, stovetop

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is ￥23,796
￥88,616 total
includes taxes & fees
Apr 20 - Apr 21
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Beach nearby, sun loungers, beach towels

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, (13 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is ￥45,688
￥94,584 total
includes taxes & fees
Apr 21 - Apr 22
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (2 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 ￥36,646
￥76,553 total
includes taxes & fees
Apr 29 - Apr 30
Sunset Cottage - West River Access and Views!
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (43 reviews)
"The place was vey clean, whic is of upmost improtance to me. We loved the veiw and the location."
United States
Crystal H.
The price is ￥56,317
￥70,247 total
includes taxes & fees
May 6 - May 7
Sunset Breezes - quiet waterfront retreat
Living area

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
The price is ￥23,637
￥92,063 total
includes taxes & fees
Apr 20 - Apr 21
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Outdoor dining

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, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is ￥18,156
￥67,701 total
includes taxes & fees
Apr 22 - Apr 23
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (54 reviews)
"Great place, will stay again"
United States
Matt S.
The price is ￥36,487
￥43,385 total
includes taxes & fees
Apr 30 - May 1
Waterfront Getaway with Dock
Dining

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is ￥33,452
￥83,890 total
includes taxes & fees
May 3 - May 4
Charming Pet-Friendly Stay - Near Bay & Beaches.
Marina

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.2 out of 10, Wonderful, (5 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is ￥20,940
￥75,414 total
includes taxes & fees
Apr 20 - Apr 21
Renovated Bungalow | Walk to Beach | Dog-Friendly
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

The Wildset

The Wildset

10/10 Excellent
"The customer service in this property is top level! The location is phenomenal. "
Gail 1-night trip
Posted 2 hours ago
The Wildset

Find out more about St. Michaels

St. Michaels Vacation Homes information

Number of reviews
359
Accommodation
653 Vacation Homes
Lowest Price
￥36,470
Highest Price
￥98,346

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