Vacation rentals in St. Michaels

Top vacation rentals in St. Michaels

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

Saint Michaels MD

0.12 mi from city center

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This cottage features a garden, laundry facilities, and barbecue grills.

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

St. Michaels MD

0.07 mi from city center

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

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

St Michaels MD

0.12 mi from city center

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This cottage features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels MD

0.11 mi from city center

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This cottage features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

Modern Flat in the Heart of St. Michaels – Walk Everywhere

Saint Michaels MD

0.08 mi from city center

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This apartment features laundry facilities.

Kitchen

Washer

Floating 2 bed 2 bath condo stunning views of the bay

Stevensville MD

11.66 mi from city center

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This houseboat features barbecue grills.

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

Stevensville MD

11.17 mi from city center

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This vacation home features a garden, laundry facilities, and barbecue grills.

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Annapolis MD

19.32 mi from city center

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This vacation home features a garden, laundry facilities, and concierge services. Barbecue grills are provided for your convenience.

Kitchen

Washer

Cass-N-Reel Luxury Houseboat

Grasonville MD

12.69 mi from city center

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Stay at this houseboat in Grasonville. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chesapeake Bay Environmental Center and Paul Reed Smith Guitars are located nearby.

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis MD

19.47 mi from city center

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This vacation home features laundry facilities.

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge MD

16.63 mi from city center

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This vacation home features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Laundry facilities are provided for your convenience.

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

Annapolis MD

20.87 mi from city center

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A gym is featured at this vacation home, along with limo/town car service and a garden. Laundry facilities, concierge services, and barbecue grills are also on offer.

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville MD

17.66 mi from city center

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This vacation home features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Annapolis MD

19.18 mi from city center

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This apartment features a hot tub and a sauna. A garden, laundry facilities, and barbecue grills are also on offer.

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge MD

13.4 mi from city center

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This cottage features a garden, laundry facilities, and barbecue grills.

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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 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.