St. Michaels Holiday Rentals

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Holiday Rentals in St. Michaels

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (32)
"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (115)
"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (112)
"Our stay in St Michael's was wonderful. The location of this property could not be better. Close to marina, parks, restaurants, historic downtown and the maritime museum. We never needed to use our car! Tom is an excellent host. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (202)
"Great location, great property, great communication with owner. If you stay in Annapolis, you know how stressful it is finding street parking. The included parking spot in the secure garage (directly behind the rental) was a huge bonus for this property! "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Wonderful serene location on a tributary to the Bay. Beautiful water views with its own dock and kayaks. 15 minutes to Annapolis. House is very comfortable, freshly and attractively decorated, and well stocked. Manager was extraordinarily helpful. Nine of us had a perfect relaxing long weekend. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (22)
"The pictures dont do this rental house justice. It was very clean and wonderfully decorated. The seperate unit was ideal for my daughter and her family. The "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (17)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

10.0 out of 10, Exceptional, (48)
"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

3 Story Stunner in Murray Hill <1 mile from USNA!

10.0 out of 10, Exceptional, (18)
"Very nicely renovated property in the heart of downtown Annapolis. Highly recommend for groups / families and very kid friendly. Great location to walk to all that Annapolis has to offer. "
The price is AU$1,350
includes taxes & fees
2 Dec - 3 Dec
3 Story Stunner in Murray Hill <1 mile from USNA!

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (73)
"Perfect for a romantic weekend away!"
Amazing views, short walks to great dining!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (35)
"We had a wonderful time with beautiful views at this property. There's no better way to celebrate a special birthday in the comfort and luxury of this waterfront property in MD! Will definitely consider again for future. "
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (30)
"Excellent experience."
The price is AU$382
includes taxes & fees
1 Dec - 2 Dec
Relax on Kent Island in 3 Bedroom Home w/Waterview

2-story, riverfront home with private dock, inviting deck & dog-friendly yard

9.6 out of 10, Exceptional, (12)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (100)
"We absolutely loved staying in this property. It’s comfortable, charming and so well appointed. It’s situated in a great location, within walking distance of all the special things Annapolis has to offer. The host was so easy to communicate with, and we really appreciate that she shares this beautiful home. We will’s definitely be back!"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (71)
"We had an amazing time! Beth and Andy are wonderful hosts! We are looking forward to another stay!"
The price is AU$689
includes taxes & fees
1 Dec - 2 Dec
Waterfront Oasis of Annapolis Star

USNA Quintessential Charm ~ Downtown Annapolis.

9.8 out of 10, Exceptional, (6)
"We really enjoyed this property. It was clean and tidy. Checking in was simple. Parking was straightforward once we noticed the markers giving us clear instructions. The kitchen has everything you need. I stayed in the downstairs bedroom, and the bed and pillows were very comfortable. The downstairs shower is small, but the water pressure is good. Everyone who stayed upstairs enjoyed the amenities. Definitely will try to rent this again for the next time we visit Annapolis."
USNA Quintessential Charm ~ Downtown Annapolis.

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (87)
"All as advertised Wonderful option to a hotel"
Cass-Away Luxury Houseboat
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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Other types of properties in St. Michaels you may be interested in

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1089)
"Very pleasant, comfortable and clean in a great location "
The price is AU$145
includes taxes & fees
15 Dec - 16 Dec
St Michaels Inn

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (322)
"Everything about this property was exceptional! Definitely will be back!"
The price is AU$532
includes taxes & fees
18 Dec - 19 Dec
Inn at Perry Cabin

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (282)
"Pleasantly surprised with everything- everyone has been extremely friendly and the property is fresh, clean & bright. "
The price is AU$421
includes taxes & fees
2 Dec - 3 Dec
The Wildset
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.
Beautiful view of the beach with palm trees

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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?

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife: This highly rated holiday home rental in St. Michaels offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable 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.

How many holiday rentals are there in St. Michaels?

Expedia has 33 holiday rentals for your stay in St. Michaels.

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

Cultural attractions to visit include Chesapeake Bay Maritime Museum and St. Michaels Museum. St. Michaels Winery and Avalon Theatre are a couple of places you'll find in the wider area.

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.