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

St. Michaels Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for St. Michaels holiday 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, (48 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 HK$685
HK$2,156 total
includes taxes & fees
23 Jul - 24 Jul
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (41 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is HK$1,102
HK$2,695 total
includes taxes & fees
4 Aug - 5 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior detail

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is HK$981
HK$2,522 total
includes taxes & fees
23 Jul - 24 Jul
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
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 HK$1,200
HK$2,169 total
includes taxes & fees
28 Jul - 29 Jul
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Beach nearby

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)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is HK$1,838
HK$4,054 total
includes taxes & fees
13 Aug - 14 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (37 reviews)
"Can’t wait to come back!"
United States
Tiffany K.
The price is HK$1,215
HK$1,995 total
includes taxes & fees
23 Jul - 24 Jul
Sailwinds Loft at Cambridge Creek
Terrace/patio

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
The price is HK$1,489
HK$3,056 total
includes taxes & fees
23 Jul - 24 Jul
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Outdoor dining

Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (1 review)
"Great spot! Amazing amount of room. Great communication in ease of check-in"
United States
Jeffrey T.
Waterfront Escape with Pool Nature Lover Paradise
Marina

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

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.0 out of 10, Very good, (8 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is HK$1,647
HK$3,183 total
includes taxes & fees
28 Jul - 29 Jul
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (23 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 HK$2,078
HK$3,939 total
includes taxes & fees
28 Jul - 29 Jul
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Coffee/tea maker, fridge, microwave, oven

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (9 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 HK$1,513
HK$4,335 total
includes taxes & fees
23 Jul - 24 Jul
Renovated Bungalow | Walk to Beach | Dog-Friendly
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, (12 reviews)
"Great space. Great location for exploring Cambridge on foot. Check-in easy. Everything clean. Everything works."
United States
Peter G.
The price is HK$2,156
HK$3,915 total
includes taxes & fees
28 Jul - 29 Jul
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
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 HK$2,039
HK$3,898 total
includes taxes & fees
28 Jul - 29 Jul
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
TV, offices

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,897
HK$5,435 total
includes taxes & fees
29 Jul - 30 Jul
Family Home on Mayo Peninsula | Deck | Sleeps 10
Smart TV

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 HK$3,303
HK$5,704 total
includes taxes & fees
5 Aug - 6 Aug
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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, (26 reviews)
"Kitchen was fully stocked, apartment very clean, very nice host and parking was great"
United States
Tara K.
The price is HK$924
HK$2,224 total
includes taxes & fees
23 Jul - 24 Jul
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Interior

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 HK$1,568
HK$4,443 total
includes taxes & fees
18 Aug - 19 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!
Interior

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 HK$2,564
HK$4,715 total
includes taxes & fees
28 Jul - 29 Jul
Sunset Cottage - West River Access and Views!
Beach nearby, sun-loungers, beach towels

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, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$2,858
HK$5,511 total
includes taxes & fees
4 Aug - 5 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (85 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$2,117
HK$3,880 total
includes taxes & fees
26 Jul - 27 Jul
Waterfront Oasis of Annapolis Star
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Only stayed one night, but it was an excellent value and very convenient to where I needed to be. Friendly and helpful staff."
Randall 1-night trip
Posted 6 hours ago
Crowne Plaza Annapolis by IHG

Find out more about St. Michaels

Search for holiday rentals in St. Michaels on Expedia! You can easily find your home rentals, villas, holiday apartments in St. Michaels using one of the methods below:

  • View our selection of featured holiday rentals in St. Michaels
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Look no further and take a look at our great range of rental properties in St. Michaels!

Frequently asked questions

Are there holiday rentals in St. Michaels?

Yes, there are holiday rentals in St. Michaels close to Chesapeake Bay Maritime Museum, or you can select 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 holiday rentals that St. Michaels has to offer?

St. Michaels Escape | Pool, Hot Tub & Fire Pit: This highly rated holiday home rental in St. Michaels is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in St. Michaels?

Expedia has 34 holiday 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 Saint Michaels Town Hall and St. Michaels Marina.

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

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in St. Michaels. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.