Holiday Rentals in St. Michaels

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Our top choices for St. Michaels holiday rentals

9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is €337
includes taxes & fees
24 Mar - 25 Mar
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.8 out of 10, Exceptional, (12 reviews)
"Host was personally accessible during stay, responded quickly, and went the extra mile with wonderful touches left around the place."
United States
John S.
The price is €364
includes taxes & fees
16 Apr - 17 Apr
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
10.0 out of 10, Exceptional, (10 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is €337
includes taxes & fees
24 Mar - 25 Mar
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is €366
includes taxes & fees
6 Apr - 7 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
10.0 out of 10, Exceptional, (7 reviews)
"The property was clean, accurate to the listing and to prior feedback from other visitors. We loved the area; very quaint and cute. We enjoyed our stay and would recommend it to anyone looking for a cozy place to stay. "
United States
Amanda S.
The price is €309
includes taxes & fees
24 Mar - 25 Mar
Station House East: Upscale Loft in the Historic District Cambridge, MD
8.8 out of 10, Excellent, (10 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is €527
includes taxes & fees
24 Mar - 25 Mar
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is €217
includes taxes & fees
25 Mar - 26 Mar
Sailwinds Loft at Cambridge Creek
8.4 out of 10, Very good, (6 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is €269
includes taxes & fees
25 Mar - 26 Mar
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
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 €414
includes taxes & fees
24 Mar - 25 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is €353
includes taxes & fees
24 Mar - 25 Mar
Waterfront Oasis of Annapolis Star
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is €213
includes taxes & fees
24 Mar - 25 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!
10.0 out of 10, Exceptional, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is €248
includes taxes & fees
24 Mar - 25 Mar
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
9.8 out of 10, Exceptional, (12 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is €458
includes taxes & fees
24 Mar - 25 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is €282
includes taxes & fees
12 Apr - 13 Apr
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is €401
includes taxes & fees
22 Apr - 23 Apr
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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 €306
includes taxes & fees
1 Apr - 2 Apr
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is €450
includes taxes & fees
24 Mar - 25 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Holiday Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is €460
includes taxes & fees
24 Mar - 25 Mar
Cute bungalow blocks to Stadium
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
Wright's Cottage- Pet's Welcome & EV Charging
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is €535
includes taxes & fees
13 Apr - 14 Apr
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
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

Find out more about St. Michaels

Everything you need to know about St. Michaels holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the St. Michaels holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect St. Michaels holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

St. Michaels holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in St. Michaels. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A St. Michaels holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of St. Michaels holiday rentals we have selected for you start as low as €213 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on St. Michaels rentals

At Expedia, we put the best St. Michaels holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top St. Michaels rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream St. Michaels holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around St. Michaels. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This holiday home rental outside of St. Michaels is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

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 St. Michaels Marina and St. Michaels Winery.

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.