St. Michaels Holiday Rentals

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Holiday Rentals in St. Michaels

Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.

9.6 out of 10, Exceptional, (5)
"We had a great week in Cambridge. The Retro House has everything you need. It’s neat, clean, bright and very easy to stay in. It’s in a quiet neighborhood just short drive from the center of town. This was our second stay in the Retro House, we love it & will be coming back in the spring for another week!"
The price is AU$591
includes taxes & fees
21 July - 22 July
Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AU$504
includes taxes & fees
23 July - 24 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
Gorgeous Creek Side Ranch-Style Estate With Dock

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
The price is AU$444
includes taxes & fees
21 July - 22 July
Cozy Home in Beautiful Annapolis

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"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!"
The price is AU$691
includes taxes & fees
27 July - 28 July
Bayside Cottage steps from Rock Hall Harbor

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (5)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is AU$700
includes taxes & fees
22 July - 23 July
HGTV quality, private guest suite, country getaway with hot tub & fire pit

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

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is AU$556
includes taxes & fees
3 Aug - 4 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (39)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is AU$757
includes taxes & fees
20 July - 21 July
Beautiful Waterfront Retreat in Cambridge!

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

9.2 out of 10, Wonderful, (5)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is AU$682
includes taxes & fees
22 July - 23 July
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is AU$659
includes taxes & fees
17 July - 18 July
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (1)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is AU$787
includes taxes & fees
21 July - 22 July
Charming Pet-Friendly Stay - Near Bay & Beaches.

Cute bungalow blocks to Stadium

10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
The price is AU$866
includes taxes & fees
21 July - 22 July
Cute bungalow blocks to Stadium

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (10)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is AU$821
includes taxes & fees
21 July - 22 July
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (1)
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home "
The price is AU$738
includes taxes & fees
17 July - 18 July
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is AU$700
includes taxes & fees
28 July - 29 July
The Cottage

Waterfront Camper with Dock

10.0 out of 10, Exceptional, (1)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is AU$532
includes taxes & fees
17 July - 18 July
Waterfront Camper with Dock

Neptune by the Water

9.8 out of 10, Exceptional, (9)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is AU$780
includes taxes & fees
20 July - 21 July
Neptune by the Water

3 BR Pet Friendly Beverly Beach Cottage

9.8 out of 10, Exceptional, (7)
" Retreating from a construction project in our home, we landed in Grandma's Cottage. What a delightful semi-vactation. Lovely cottage, kind and friendly commuity srrouned by water and nature parks."
The price is AU$717
includes taxes & fees
17 July - 18 July
3 BR Pet Friendly Beverly Beach Cottage

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (45)
"We appreciated the cleanliness of the home and the location was beautiful and convenient to the state/national park, town and Harriet Tubman museum."
The price is AU$433
includes taxes & fees
23 July - 24 July
Waterfront Getaway with Dock

Dean Street's Lower Deck House!

The price is AU$697
includes taxes & fees
3 Aug - 4 Aug
Dean Street's Lower Deck House!
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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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?

The Cozy Crab- Your Charming Haven in Lovely North Beach!: This holiday home rental outside of St. Michaels offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals are there in St. Michaels?

Expedia has 35 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.