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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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, (56 reviews)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is €252
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Three birds perched on a wooden structure by the water.

2. 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 €1,232
includes taxes & fees
15 Nov - 16 Nov
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A lighthouse with a white exterior, a balcony, and a metal roof.

3. 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 €679
includes taxes & fees
30 Oct - 31 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A two-story house with a red roof, a brick chimney, and a small porch.

4. 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 €935
includes taxes & fees
27 Oct - 28 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.

5. 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, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is €1,234
includes taxes & fees
16 Nov - 17 Nov
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

6. 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 €465
includes taxes & fees
19 Oct - 20 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

7. 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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is €299
includes taxes & fees
29 Oct - 30 Oct
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

8. 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 €262
includes taxes & fees
18 Oct - 19 Oct
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A wooden dock extending into a calm body of water with boats docked at the end.

9. 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 €430
includes taxes & fees
16 Nov - 17 Nov
Cozy 2br home w/ parking in downtown Annapolis
A beach with chairs and a pier 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 €480
includes taxes & fees
3 Nov - 4 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

11. 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)
"Pet friendly!"
United States
Mary Beth S.
The price is €359
includes taxes & fees
16 Nov - 17 Nov
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A bunk bed with a wooden frame, white bedding, and a blue pillow with a floral design.

12. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (3 reviews)
"Warm and cozy- amazing home, beautiful area"
United States
Sodbileg
Rose Haven Coastal Cottage
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

13. 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 €441
includes taxes & fees
29 Oct - 30 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A bedroom with a bed, dresser, and a door.

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

More, than just a place to sleep - welcome home!
Cambridge
The price is €361
includes taxes & fees
26 Oct - 27 Oct
More, than just a place to sleep - welcome home!
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

15. 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 €430
includes taxes & fees
14 Nov - 15 Nov
3-bedroom house in Deale located on Bay many amenities and great views
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 €463
includes taxes & fees
16 Nov - 17 Nov
Sunset Cottage - West River Access and Views!
A deck with outdoor furniture, a red door, and a house with windows.

17. 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 €335
includes taxes & fees
26 Oct - 27 Oct
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.

18. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (67 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is €248
includes taxes & fees
15 Nov - 16 Nov
Waterfront Getaway with Dock
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 €534
includes taxes & fees
29 Oct - 30 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
Pool

20. 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 €411
includes taxes & fees
27 Oct - 28 Oct
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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

The Wildset

The Wildset

10/10 Excellent
"Loved my stay at Wildset. Place is very clean, cozy & comfortable. Staff very friendly. Convenience to everything in town. Only 2 issues I had was how long it took shower water to get hot. And it wasn’t super hot. Not sure if it was cause I was in main building. Other was a knocking noise which seemed to happen primarily while restaurant was open. Not sure if it was from the dishwasher or some other equipment. I’m a light sleeper too so some people may be able to sleep thru it. Would def stay here again!!"
Bonnie 2-night trip
Posted less than an hour ago
The Wildset

Find out more about St. Michaels

St. Michaels Holiday Homes information

Number of reviews
490
Accommodation
640 Holiday Homes
Lowest Price
€248
Highest Price
€1,234