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Holiday Rentals in Shady Side
![Directly Across from Gate One & Steps from the Waterfront](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/8a65e5c6_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Directly Across from Gate One & Steps from the Waterfront
![421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!](https://images.trvl-media.com/lodging/67000000/66850000/66845500/66845427/8732960a_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
![Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/d8a574c5_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
![Cozy place close to the city dock](https://images.trvl-media.com/lodging/65000000/64680000/64676800/64676744/0842e88f_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Cozy place close to the city dock
![Pool and Bay Views on wrap around deck in Kent Island](https://images.trvl-media.com/lodging/64000000/63510000/63505500/63505478/902d890f_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Pool and Bay Views on wrap around deck in Kent Island
![Rockhold Creek Cottage, Water Front, Vacation Home, Docks](https://images.trvl-media.com/lodging/23000000/22400000/22392900/22392832/25d11972_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
![Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.](https://images.trvl-media.com/lodging/84000000/83960000/83955900/83955892/8dbe0997_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
![Anchor's Away in the Heart of Eastport!](https://images.trvl-media.com/lodging/64000000/63880000/63870100/63870050/dd4d84f7_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Anchor's Away in the Heart of Eastport!
![Amazing views, short walks to great dining!](https://images.trvl-media.com/lodging/68000000/67640000/67633400/67633374/8853efa7_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Amazing views, short walks to great dining!
![Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/7141469b_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
![Waterfront Oasis of Annapolis Star](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/a4747c62_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Waterfront Oasis of Annapolis Star
![Charming Annapolis WaterVIEW Home](https://images.trvl-media.com/lodging/38000000/37270000/37267300/37267284/f3a9f086_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Charming Annapolis WaterVIEW Home
![Relaxing Waterfront Cottage Near St Michaels, Maryland](https://images.trvl-media.com/lodging/20000000/19450000/19447700/19447633/c4596021_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Relaxing Waterfront Cottage Near St Michaels, Maryland
![Relax on Kent Island in 3 Bedroom Home w/Waterview](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/05a0120a_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Relax on Kent Island in 3 Bedroom Home w/Waterview
Holiday Rentals in Shady Side
When it comes to going on a break to Shady Side, you can go the traditional route with a hotel, or see things from a new, exciting perspective with your very own Shady Side holiday rental. The price difference alone makes it a tantalising prospect, as you’ll enjoy huge savings on nightly rates when you go for your own apartment, villa or cottage rather than a hotel stay. But there are so many other perks, beyond simply getting more bang for your buck.
There’s the sense of instantly becoming a “local” to the area, rather than just a box-ticking tourist. From the moment you set foot through the front door, a holiday rental in Shady Side will become your home away from home, where you can relax in the living spaces and cook your own meals in the kitchen – perhaps with fresh, locally-sourced ingredients from a bustling food market close by.
The feeling of real privacy is another major benefit that comes with Shady Side holiday rentals. Whether you go for a sleek apartment, smart villa or cosy cottage, you won’t be in a busy tourist temple with hotel staff and other travellers around you all the time – you’ll have your own space where you can enjoy your holiday at your own pace. Have breakfast at your leisure at the kitchen table, chat over your list of must-dos in the living room, and then head out for hours of sightseeing before returning for your later afternoon siesta in a space which is truly your own.
You’ll also have a serious variety of possible pads to choose from. With ebookers, finding the right place is a doddle. You can search for contemporary apartments with sleek decor, ideal for a romantic getaway, or select a large villa where every member of the family gets to kick back in their own spacious bedroom.
To make it easier to pinpoint the exact right Shady Side holiday rental, you can use our map to find villas, cottages and apartments close to major landmarks and attractions, so you can choose to be in the thick of the action or in a more quiet and serene area. Just select your preferred travel dates and you’ll be able to find the best, most recently updated deals on Shady Side holiday rentals in moments.