A waterfront street lined with trees and a white building with a balcony.

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for St. Michaels holiday homes

Exterior

1. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is HK$966
HK$2,527 total
includes taxes & fees
16 Sept - 17 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

2. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is HK$1,010
HK$2,451 total
includes taxes & fees
17 Sept - 18 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
Dining

3. 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, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is HK$1,960
HK$3,283 total
includes taxes & fees
8 Sept - 9 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Beach

4. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is HK$518
HK$2,407 total
includes taxes & fees
7 Sept - 8 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Marina

5. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is HK$1,411
HK$3,125 total
includes taxes & fees
28 Sept - 29 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Beach

6. 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, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$1,482
HK$3,665 total
includes taxes & fees
9 Sept - 10 Sept
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Outdoor dining

7. 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, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is HK$1,105
HK$3,602 total
includes taxes & fees
22 Sept - 23 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Exterior

8. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
6.8 out of 10, (3 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveller
The price is HK$5,645
HK$8,261 total
includes taxes & fees
7 Sept - 8 Sept
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Pool

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$1,129
HK$3,584 total
includes taxes & fees
7 Sept - 8 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Living area

10. 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, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is HK$2,967
HK$5,256 total
includes taxes & fees
6 Oct - 7 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Interior

11. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is HK$2,360
HK$4,413 total
includes taxes & fees
9 Sept - 10 Sept
Sunset Cottage - West River Access and Views!
Outdoor dining

12. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is HK$579
HK$1,947 total
includes taxes & fees
21 Sept - 22 Sept
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Beach

13. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (74 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is HK$5,880
HK$10,385 total
includes taxes & fees
7 Sept - 8 Sept
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Exterior

14. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is HK$6,272
HK$10,878 total
includes taxes & fees
7 Sept - 8 Sept
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Living area

15. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$2,068
HK$5,771 total
includes taxes & fees
7 Sept - 8 Sept
Family Home on Mayo Peninsula | Deck | Sleeps 10
Outdoor dining

16. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (76 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is HK$3,183
HK$6,078 total
includes taxes & fees
8 Sept - 9 Sept
Charming Annapolis WaterVIEW Home
Living area

17. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is HK$1,757
HK$4,023 total
includes taxes & fees
29 Sept - 30 Sept
3-bedroom house in Deale located on Bay many amenities and great views
Interior

18. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,944
HK$4,916 total
includes taxes & fees
22 Sept - 23 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
Outdoor dining

19. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is HK$2,893
HK$3,602 total
includes taxes & fees
4 Oct - 5 Oct
Sunset Breezes - quiet waterfront retreat
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

8/10 Good
"Ver nice older hotel but well maintained. Spacious rooms and good breakfast. My only complaint is that you can tell they also keep long term tenants as there were cats roaming around (which didn’t bother me but might others) and bikes/trash outside some of the rooms and plants in windows. A normal nightly rental hotel would not allow this id think so it made the atmosphere seem a lil run down even if the room was decent."
Amy 1-night trip
Posted 1 hour ago
Sonesta ES Suites Annapolis

Find out more about St. Michaels

St. Michaels Vacation Homes information

Number of reviews
370
Accommodation
645 Vacation Homes
Lowest Price
HK$1,947
Highest Price
HK$10,878

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