St. Michaels Vacation Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for St. Michaels vacation rentals

Exterior

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, (45 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is SAR 390
SAR 1,058 total
includes taxes & fees
8 Jun - 9 Jun
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (21 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is SAR 995
SAR 1,866 total
includes taxes & fees
8 Jun - 9 Jun
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (30 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is SAR 582
SAR 955 total
includes taxes & fees
8 Jun - 9 Jun
Sailwinds Loft at Cambridge Creek
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is SAR 465
SAR 1,086 total
includes taxes & fees
30 Jun - 1 Jul
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Exterior

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is SAR 390
SAR 1,102 total
includes taxes & fees
9 Jun - 10 Jun
Charming Coastal/Country Home w/3 Acres & Sauna!
Dining

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, (13 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 SAR 938
SAR 1,571 total
includes taxes & fees
8 Jun - 9 Jun
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Marina

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
7.8 out of 10, Good, (7 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is SAR 807
SAR 1,532 total
includes taxes & fees
8 Jun - 9 Jun
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (57 reviews)
"Great place, will stay again"
United States
Matt S.
The price is SAR 863
SAR 1,046 total
includes taxes & fees
8 Jun - 9 Jun
Waterfront Getaway with Dock
Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is SAR 957
SAR 1,823 total
includes taxes & fees
8 Jun - 9 Jun
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Downtown Cambridge
10.0 out of 10, Exceptional, (11 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is SAR 1,032
SAR 1,910 total
includes taxes & fees
8 Jun - 9 Jun
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is SAR 739
SAR 1,464 total
includes taxes & fees
30 Jun - 1 Jul
Bayside Cottage steps from Rock Hall Harbor
1 bedroom, iron/ironing board, WiFi, bed sheets

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is SAR 537
SAR 991 total
includes taxes & fees
23 Jun - 24 Jun
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (23 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is SAR 589
SAR 1,578 total
includes taxes & fees
8 Jun - 9 Jun
Walk to Beach! King Bed & Free Beach Passes
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is SAR 963
SAR 1,795 total
includes taxes & fees
7 Jun - 8 Jun
Waterfront Oasis of Annapolis Star
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is SAR 808
SAR 1,028 total
includes taxes & fees
7 Jun - 8 Jun
Sailboat Experience in Annapolis
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
The price is SAR 1,010
SAR 2,234 total
includes taxes & fees
8 Jun - 9 Jun
Charming Annapolis WaterVIEW Home
Outdoor dining

Waterfront Unit | Dock, Kayaks & SUPs Included

Waterfront Unit | Dock, Kayaks & SUPs Included
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is SAR 784
SAR 1,810 total
includes taxes & fees
7 Jun - 8 Jun
Waterfront Unit | Dock, Kayaks & SUPs Included
Fridge, microwave, oven, stovetop

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.4 out of 10, Exceptional, (6 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is SAR 784
SAR 2,148 total
includes taxes & fees
6 Jun - 7 Jun
Renovated Bungalow | Walk to Beach | Dog-Friendly
Fridge, microwave, oven, stovetop

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is SAR 784
SAR 1,883 total
includes taxes & fees
8 Jun - 9 Jun
Pool Loft Suite | Bay Access & Beach Passes
Marina

Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Marina Views • 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 SAR 1,498
SAR 3,310 total
includes taxes & fees
8 Jun - 9 Jun
Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Spacious rooms. Clean. Great area."
Alan 1-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

Are there vacation rentals in St. Michaels?

Yes, we have vacation rentals in St. Michaels close to Chesapeake Bay Maritime Museum, or you can choose a more secluded option if you're looking for a relaxing stay. The waterfront and shops are just a few reasons why tourists like St. Michaels. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best vacation rentals in St. Michaels?

Dollhouse in Central Historic St Michaels: Visitors like this St. Michaels vacation home rental. It offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in St. Michaels?

Expedia has 35 vacation rentals for your stay in St. Michaels.

What’s there to see and do in St. Michaels?

Cultural attractions include Chesapeake Bay Maritime Museum and St. Michaels Museum, whereas Church Cove Park and CL Open Field are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include St. Michaels Marina and St. Michaels Winery.

What’s a vacation rental in St. Michaels like?

Vacation rentals are private properties where you can stay for short or long periods in St. Michaels. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.