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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for St. Michaels holiday homes

A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

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, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is HK$633
HK$2,183 total
includes taxes & fees
26 Oct - 27 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (48 reviews)
"Great stay"
United States
Michael V.
The price is HK$554
HK$2,087 total
includes taxes & fees
25 Oct - 26 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
Three birds perched on a wooden structure by the water.

3. 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, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is HK$5,885
HK$10,260 total
includes taxes & fees
28 Oct - 29 Oct
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

4. 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, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is HK$1,934
HK$3,997 total
includes taxes & fees
25 Oct - 26 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

5. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is HK$1,020
HK$2,404 total
includes taxes & fees
25 Oct - 26 Oct
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A two-story house with a red roof, a brick chimney, and a small porch.

6. 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
8.4 out of 10, Very good, (6 reviews)
"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...
United States
Michele F.
The price is HK$5,650
HK$8,268 total
includes taxes & fees
24 Oct - 25 Oct
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

7. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is HK$5,493
HK$9,758 total
includes taxes & fees
26 Oct - 27 Oct
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Living area

8. 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, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is HK$565
HK$2,374 total
includes taxes & fees
23 Oct - 24 Oct
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A brick building with a white porch and a well-maintained lawn.

9. 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, (26 reviews)
The price is HK$1,373
HK$3,094 total
includes taxes & fees
17 Nov - 18 Nov
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A hot tub with a white deck and railing, surrounded by trees and a house in the background.

10. 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$1,726
HK$4,008 total
includes taxes & fees
9 Nov - 10 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A cozy outdoor seating area with a fire pit, a wooden table, and chairs.

11. 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, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is HK$908
HK$3,270 total
includes taxes & fees
25 Oct - 26 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

12. 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$1,412
HK$3,426 total
includes taxes & fees
27 Oct - 28 Oct
3-bedroom house in Deale located on Bay many amenities and great views
A deck with outdoor furniture, a red door, and a house with windows.

13. 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
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is HK$1,349
HK$2,969 total
includes taxes & fees
28 Oct - 29 Oct
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A bedroom with a bed, a bedside table, a window with curtains, and a view of the sea.

14. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is HK$2,338
HK$3,117 total
includes taxes & fees
23 Oct - 24 Oct
More, than just a place to sleep - welcome home!
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

15. 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$2,025
HK$2,555 total
includes taxes & fees
17 Nov - 18 Nov
Sunset Breezes - quiet waterfront retreat
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

16. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 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 HK$1,946
HK$3,965 total
includes taxes & fees
10 Nov - 11 Nov
Sunset Cottage - West River Access and Views!
A waterfront walkway with a brick path, a lamp post, and a bench.

17. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is HK$1,962
HK$3,766 total
includes taxes & fees
16 Nov - 17 Nov
Cozy 2br home w/ parking in downtown Annapolis
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$2,072
HK$5,779 total
includes taxes & fees
25 Oct - 26 Oct
Family Home on Mayo Peninsula | Deck | Sleeps 10
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

19. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is HK$1,511
HK$4,353 total
includes taxes & fees
25 Oct - 26 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

20. 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$1,569
HK$4,500 total
includes taxes & fees
17 Nov - 18 Nov
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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"The Hotel was excellent. However, Expedia did not disclose that there was an additional charge for resort fee that was not included in the quoted price from Expedia. There was an additional $33.00 when I checked into the hotel. I could have gone with a different online reservation cheaper."
William 1-night trip
Posted 5 hours ago
Rod 'N' Reel Resort

Find out more about St. Michaels

St. Michaels Vacation Homes information

Number of reviews
474
Accommodation
645 Vacation Homes
Lowest Price
HK$2,087
Highest Price
HK$10,260

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