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

Holiday Homes in St. Michaels

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for St. Michaels holiday homes

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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 AU$426
includes taxes & fees
13 Sept - 14 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A lighthouse with a white exterior, a balcony, and a metal roof.

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 AU$445
includes taxes & fees
17 Sept - 18 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

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 AU$570
includes taxes & fees
17 Sept - 18 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

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, (23 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AU$435
includes taxes & fees
13 Sept - 14 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

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 AU$536
includes taxes & fees
12 Oct - 13 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A wooden deck with two wicker chairs, a railing, and a view of a marina with boats and buildings in the background.

6. Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown

Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown
Cambridge
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wouldn't hesitate to come back and stay for a few days. Beautiful home overlooking the docks."
United States
mike
The price is AU$997
includes taxes & fees
14 Sept - 15 Sept
Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown
A beach with chairs and a pier in the background.

7. 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)
"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."
United States
Sharon Z.
The price is AU$621
includes taxes & fees
14 Sept - 15 Sept
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

8. 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 AU$552
includes taxes & fees
14 Sept - 15 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A deck with outdoor furniture, a red door, and a house with windows.

9. 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 AU$349
includes taxes & fees
21 Sept - 22 Sept
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

10. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (66 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is AU$347
includes taxes & fees
16 Sept - 17 Sept
Waterfront Getaway with Dock
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

11. 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 AU$990
includes taxes & fees
12 Sept - 13 Sept
Family Home on Mayo Peninsula | Deck | Sleeps 10
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

12. 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 AU$1,009
includes taxes & fees
29 Sept - 30 Sept
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A two-story house with a red roof, a brick chimney, and a small porch.

13. 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
7.6 out of 10, Good, (4 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 AU$1,409
includes taxes & fees
15 Sept - 16 Sept
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

14. 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 AU$832
includes taxes & fees
16 Sept - 17 Sept
Sunset Cottage - West River Access and Views!
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

15. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AU$634
includes taxes & fees
16 Sept - 17 Sept
Plum Point Cottage #17
Three birds perched on a wooden structure by the water.

16. 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 AU$1,803
includes taxes & fees
14 Sept - 15 Sept
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

17. 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 AU$672
includes taxes & fees
22 Sept - 23 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

18. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (77 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 AU$1,074
includes taxes & fees
16 Sept - 17 Sept
Charming Annapolis WaterVIEW Home
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

19. 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 AU$1,974
includes taxes & fees
15 Sept - 16 Sept
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
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 AU$843
includes taxes & fees
6 Oct - 7 Oct
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Property about 1.5 miles from the center of town. We knew about the location and we were quite pleased with everything and the eggs in the buffet were excellent for a hotel breakfast.....much better than other hotels"
Gary 2-night trip
Posted 11 hours ago
St Michaels Inn

Find out more about St. Michaels

St. Michaels Holiday Homes information

Number of reviews
271
Accommodation
641 Holiday Homes
Lowest Price
AU$349
Highest Price
AU$1,974