Search Vacation Homes in St. Michaels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for St. Michaels vacation homes

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 AED 716
AED 1,530 total
includes taxes & fees
14 Apr - 15 Apr
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, (12 reviews)
"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. "
United States
Joe C.
The price is AED 918
AED 1,538 total
includes taxes & fees
14 Apr - 15 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 AED 1,142
AED 2,269 total
includes taxes & fees
14 Apr - 15 Apr
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

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 AED 643
AED 1,335 total
includes taxes & fees
14 Apr - 15 Apr
Bayside Cottage steps from Rock Hall Harbor

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 AED 1,256
AED 1,566 total
includes taxes & fees
6 May - 7 May
Sunset Breezes - quiet waterfront retreat

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 AED 633
AED 1,781 total
includes taxes & fees
14 Apr - 15 Apr
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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 AED 252
AED 914 total
includes taxes & fees
19 Apr - 20 Apr
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 AED 285
AED 952 total
includes taxes & fees
19 Apr - 20 Apr
Charming Coastal/Country Home w/3 Acres & Sauna!

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 AED 624
AED 1,611 total
includes taxes & fees
20 Apr - 21 Apr
Family Beach House: Spacious Deck, Grill & Views

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 AED 657
AED 1,269 total
includes taxes & fees
10 May - 11 May
Adorable two-bedroom retreat close to Easton, Denton, Centreville

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 AED 964
AED 1,952 total
includes taxes & fees
14 Apr - 15 Apr
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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 AED 436
AED 1,358 total
includes taxes & fees
19 Apr - 20 Apr
Walk to Beach! King Bed & Free Beach Passes

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 AED 1,124
AED 2,274 total
includes taxes & fees
20 Apr - 21 Apr
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 AED 551
AED 2,077 total
includes taxes & fees
19 Apr - 20 Apr
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

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 AED 757
AED 1,929 total
includes taxes & fees
20 Apr - 21 Apr
Cute bungalow blocks to Stadium

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 AED 581
AED 1,769 total
includes taxes & fees
19 Apr - 20 Apr
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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 AED 861
AED 2,053 total
includes taxes & fees
4 May - 5 May
Charming Pet-Friendly Stay - Near Bay & Beaches.

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 AED 485
AED 1,708 total
includes taxes & fees
14 Apr - 15 Apr
Renovated Bungalow | Walk to Beach | Dog-Friendly

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 AED 845
AED 989 total
includes taxes & fees
29 Apr - 30 Apr
Waterfront Getaway with Dock

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
The price is AED 558
AED 2,148 total
includes taxes & fees
14 Apr - 15 Apr
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
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.
Save an average of 15% on thousands of hotels when you're signed in

Top St. Michaels Hotel Reviews