Vacation rentals in St. Michaels

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Top vacation rentals in St. Michaels

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

0.07 mi from city center
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This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

0.12 mi from city center
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This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

2 out of 5
11.66 mi from city center
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This houseboat features barbecue grills.
Kitchen
Pet friendly
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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

19.34 mi from city center
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This vacation home features a water park, laundry facilities, and barbecue grills.
Kitchen
Washer
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

9.42 mi from city center
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A sauna is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

18.18 mi from city center
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This vacation home includes a garden and barbecue grills.
Kitchen
Air conditioning
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

20.36 mi from city center
$407 nightly
The price is $463 total per night
$463 total
Jul 26 - Jul 27
Total includes taxes and fees
A water park and an outdoor pool are featured at this smoke-free apartment. Barbecue grills are provided for your convenience.
Pool
Kitchen
Quiet Relaxing Waterfront Suisse Chalet

Quiet Relaxing Waterfront Suisse Chalet

19.49 mi from city center
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A water park and a hot tub are featured at this smoke-free vacation home. A garden, laundry facilities, and barbecue grills are also on offer.
Hot Tub
Kitchen
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

16.71 mi from city center
$496 nightly
The price is $526 total per night
$526 total
Aug 24 - Aug 25
Total includes taxes and fees
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

10.23 mi from city center
$265 nightly
The price is $281 total per night
$281 total
Jul 27 - Jul 28
Total includes taxes and fees
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Chesapeake Houseboat Getaway on Kent Island, Maryland

Chesapeake Houseboat Getaway on Kent Island, Maryland

11.55 mi from city center
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This houseboat features barbecue grills.
Kitchen
Pet friendly
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

11.17 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

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

18.15 mi from city center
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This vacation home features an outdoor pool and a hot tub. There's a sauna on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
Spacious 4 Bedroom Home w/ Hot Tub

Spacious 4 Bedroom Home w/ Hot Tub

18.02 mi from city center
$511 nightly
The price is $548 total per night
$548 total
Aug 25 - Aug 26
Total includes taxes and fees
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

14.63 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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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.

The Best Way to Find your Vacation Rentals in St. Michaels

How cheap can a vacation rental in St. Michaels be?

You can find vacation rentals in St. Michaels for as low as $281 per night.

How do you look for the best vacation rental deals in St. Michaels with Travelocity?

Travelocity provides the best vacation rental deals in various locations throughout St. Michaels so you can create the perfect plan for you. You can search and filter by type of property, amenities, neighborhood, price range, number of bedrooms, and more.

Are cancellations free on vacation rentals with Travelocity?

Each vacation rental has its own cancellation policy. It’s essential to understand the terms of your agreement before booking. Most rentals in St. Michaels can be canceled for free when notifying the property before the cancellation deadline.

What types of vacation rentals are available in St. Michaels?

Short term rentals come in all shapes and sizes. Choose from properties for a wide range of budgets and types of holidays. Families, couples, outdoor adventurers, and leisure travelers alike will find the perfect place for them. Check out our St. Michaels vacation apartments to get started building your trip.

What are the benefits of booking a short-term rental in St. Michaels?

Whether it’s for a summer getaway, a winter excursion, or a routine business trip, St. Michaels vacation homes are often an excellent choice. You can enjoy group vacations with short term rentals to fit your party size. You might take a romantic weekend for two or plan a family reunion, and all stay under one roof. The options are endless, and you can find them on Travelocity.

Why is Travelocity the best site to find your vacation rental in St. Michaels?

With Travelocity, all your travel needs are taken care of in one convenient platform. We offer fantastic deals on our large selection of vacation rentals to get you the most savings and rewards back on every booking. Save more when you bundle bookings together, including car rentals, flights, and activities. Here, you can build custom St. Michaels vacations.

How to cancel your vacation rental with Travelocity?

To cancel your vacation rental, contact the property manager. You can find their contact information in the ‘Itinerary’ section of your Travelocity account. Most properties receive a full refund when you cancel before the cancellation deadline. Policies vary by property, so it’s important to understand the terms before booking. For more information, visit our customer service portal.