St. Michaels Vacation Homes

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
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 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!

Stevensville

Anthony P.

HK$2,845 total

includes taxes & fees

23 Nov - 24 Nov

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!

Stevensville

Michael V.

HK$2,224 total

includes taxes & fees

3 Nov - 4 Nov

Three birds perched on a wooden structure by the water.

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

Stevensville

barbara s.

HK$9,747 total

includes taxes & fees

1 Dec - 2 Dec

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

Cambridge

Jill C.

HK$3,637 total

includes taxes & fees

9 Nov - 10 Nov

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!

North Beach

James L.

HK$2,453 total

includes taxes & fees

3 Nov - 4 Nov

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

6. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

David R.

HK$9,747 total

includes taxes & fees

2 Dec - 3 Dec

A two-story house with a red roof, a brick chimney, and a small porch.

7. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

Anonymous traveller

HK$7,858 total

includes taxes & fees

2 Nov - 3 Nov

A brick building with a white porch and a well-maintained lawn.

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

Cambridge

Mary Beth S.

HK$2,894 total

includes taxes & fees

17 Nov - 18 Nov

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

9. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...

Amelia

HK$3,425 total

includes taxes & fees

2 Nov - 3 Nov

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

Arundel on the Bay

Ryan C.

HK$3,582 total

includes taxes & fees

3 Nov - 4 Nov

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

North Beach

Johanna S.

HK$2,555 total

includes taxes & fees

2 Dec - 3 Dec

A marina with boats docked, a water tower, and residential buildings with balconies.

12. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

Cambridge

mike

HK$3,865 total

includes taxes & fees

2 Nov - 3 Nov

A dining area with a round table, chairs, and a decorative table runner.

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

Cambridge

HK$3,033 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

14. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

HK$3,185 total

includes taxes & fees

4 Nov - 5 Nov

A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

15. Sunset Breezes - quiet waterfront retreat

Dorchester County

John C.

A deck with outdoor furniture, a red door, and a house with windows.

16. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

David S.

HK$2,978 total

includes taxes & fees

5 Nov - 6 Nov

A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Edgewater

Diane D.

HK$4,150 total

includes taxes & fees

8 Nov - 9 Nov

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

Edgewater

Kristin G.

HK$5,277 total

includes taxes & fees

2 Nov - 3 Nov

A cozy outdoor seating area with a fire pit, a wooden table, and chairs.

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

North Beach

Sarah

HK$3,748 total

includes taxes & fees

16 Nov - 17 Nov

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

Chesapeak beach

Ben W.

HK$3,343 total

includes taxes & fees

3 Nov - 4 Nov

View all properties

Find holiday rentals that suit your style

Apartments

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top St. Michaels Hotel Reviews

St Michaels Inn

10/10 Excellent

"We enjoyed our stay. It was close to our event and our room was quite comfortable. The staff was very helpful to us and accommodating."

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

10/10 Excellent

"Beautiful historic home within walking distance to downtown, my now wife and I stayed for our wedding weekend and had an incredible time. The host is responsive and accommodating."

Find out more about St. Michaels