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

St. Michaels Vacation Rentals

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Our top choices for St. Michaels vacation homes

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 CA $139
CA $426 total
includes taxes & fees
Sep 23 - Sep 24
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 CA $110
CA $389 total
includes taxes & fees
Sep 21 - Sep 22
Charming Coastal/Country Home w/3 Acres & Sauna!

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 CA $385
CA $718 total
includes taxes & fees
Sep 22 - Sep 23
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

4. 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 CA $245
CA $552 total
includes taxes & fees
Oct 12 - Oct 13
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

5. 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 CA $173
CA $532 total
includes taxes & fees
Sep 28 - Sep 29
Beachside Oasis with Beach Passes & King Suite by A Haven Away

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)
"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 CA $252
CA $641 total
includes taxes & fees
Sep 22 - Sep 23
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 CA $124
CA $558 total
includes taxes & fees
Sep 24 - Sep 25
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

8. 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 CA $479
CA $870 total
includes taxes & fees
Oct 20 - Oct 21
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

9. 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 CA $386
CA $797 total
includes taxes & fees
Sep 20 - Sep 21
Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown

10. 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 CA $1,007
CA $1,474 total
includes taxes & fees
Sep 21 - Sep 22
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

11. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
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 CA $201
CA $638 total
includes taxes & fees
Sep 20 - Sep 21
Family Beach House: Spacious Deck, Grill & Views

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
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 CA $251
CA $541 total
includes taxes & fees
Sep 30 - Oct 1
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

13. 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 CA $317
CA $730 total
includes taxes & fees
Sep 30 - Oct 1
3-bedroom house in Deale located on Bay many amenities and great views

14. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is CA $316
CA $604 total
includes taxes & fees
Sep 21 - Sep 22
Rose Haven Coastal Cottage

15. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (78 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 CA $550
CA $1,044 total
includes taxes & fees
Sep 21 - Sep 22
Charming Annapolis WaterVIEW Home

16. 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 CA $1,130
CA $1,954 total
includes taxes & fees
Sep 27 - Sep 28
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

17. 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 CA $432
CA $803 total
includes taxes & fees
Oct 6 - Oct 7
Sunset Cottage - West River Access and Views!

18. 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 CA $1,118
CA $1,939 total
includes taxes & fees
Sep 20 - Sep 21
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

19. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $381
CA $646 total
includes taxes & fees
Sep 21 - Sep 22
Plum Point Cottage #17

20. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is CA $268
CA $714 total
includes taxes & fees
Oct 12 - Oct 13
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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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St. Michaels Vacation Homes information

Number of reviews
346
Accommodation
645 Vacation Homes
Lowest Price
CA $389
Highest Price
CA $1,954

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