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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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 £224
includes taxes & fees
26 Aug - 27 Aug
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, (46 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 £221
includes taxes & fees
27 Aug - 28 Aug
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 £306
includes taxes & fees
26 Aug - 27 Aug
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, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is £259
includes taxes & fees
31 Aug - 1 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A two-story house with a red roof, a brick chimney, and a small porch.

5. 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
6.8 out of 10, (3 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 £759
includes taxes & fees
23 Sept - 24 Sept
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

6. 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 £374
includes taxes & fees
23 Sept - 24 Sept
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

7. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (3 reviews)
"N"
United States
Maria S.
The price is £876
includes taxes & fees
30 Aug - 31 Aug
Waterfront Escape with Pool Nature Lover Paradise
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

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, (15 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is £442
includes taxes & fees
2 Sept - 3 Sept
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

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, (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 £306
includes taxes & fees
1 Sept - 2 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

10. 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)
"Such a great house! "
United States
Stephanie V.
The price is £329
includes taxes & fees
26 Aug - 27 Aug
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A deck with outdoor furniture, a red door, and a house with siding.

11. 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
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is £254
includes taxes & fees
30 Aug - 31 Aug
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

12. 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 £514
includes taxes & fees
26 Aug - 27 Aug
Family Home on Mayo Peninsula | Deck | Sleeps 10
A marina with boats docked, a water tower, and residential buildings with balconies.

13. Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our weekend getaway at the beautiful gated community. Great water views and a walkable community. The townhouse met all our needs. Fully stocked with essential items. The added bonus is a the workout room with top of the line equipment. A nice touch! Two great decks overlooking the marina. The owners are very responsive."
United States
Melissa
The price is £295
includes taxes & fees
1 Sept - 2 Sept
Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 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 £419
includes taxes & fees
2 Sept - 3 Sept
Renovated Bungalow | Walk to Beach | Dog-Friendly
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

15. 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 £1,018
includes taxes & fees
1 Sept - 2 Sept
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

16. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (75 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 £495
includes taxes & fees
14 Sept - 15 Sept
Charming Annapolis WaterVIEW Home
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

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)
"Lovely place and neighborhood! "
United States
Marci M.
The price is £390
includes taxes & fees
9 Sept - 10 Sept
Sunset Cottage - West River Access and Views!
Three birds perched on a wooden structure by the water.

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, (76 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is £1,011
includes taxes & fees
8 Sept - 9 Sept
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

19. 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 £452
includes taxes & fees
8 Sept - 9 Sept
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
"This is the 2nd time we've stayed at the St Michaels Inn, but the last time was 6 years ago. They are in the middle of renovating but I will say the room was clean and fairly updated. The breakfast was just like you'd see at most hotels and had plenty of seating. Parking was easy and we were in the back building which felt a little more private (our back window faced trees which kept the room dark). Check in was easy and we ended up adding an extra night's stay and despite doing that via Hotels.com, they worked to keep us in the same room. Everyone was very accommodating and when they found out my wife was a teacher, they all thanked her for her hard work. It was pleasant stay."
Robert 1-night trip
Posted 1 hour ago
St Michaels Inn

Find out more about St. Michaels

St. Michaels Holiday Homes information

Number of reviews
321
Accommodation
641 Holiday Homes
Lowest Price
£221
Highest Price
£1,018