Search Shady Side Holiday Homes from AU$145
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Featured Holiday Homes in Shady Side

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

Charming Historic Townhouse Steps From USNA

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

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

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

Charming townhome with AC and WiFi in delightful Annapolis

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Heated pool, sandy beach, pier, and playground set punch point apart!

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Rising Sun Bay View Cottage
Holiday Accommodation Shady Side
Get the Lowdown on Shady Side Holiday Homes
How much is a holiday home in Shady Side?
Depending on when you visit, you can score a holiday home in Shady Side for as little as AU$145 per night. Prices vary by property class, amenities, and location, all of which you can quickly sort through on our handy search page.
How do I find the best price for a holiday home in Shady Side?
Discover exclusive deals on Shady Side house rentals when you book with Wotif. Once you enter the dates of your trip and number of travellers (Girls’ trip? Family getaway? We’ve got you covered.), filter the results by guest rating, budget, property class, number of bedrooms, amenities, and more. You can also use the map feature to zoom in on the neighbourhood or to view several rentals at once.
Why should I book a holiday home in Shady Side?
Because there’s nothing better than having a private place to call your home away from home while exploring Shady Side. When you book a holiday house in Shady Side, you can indulge in a variety of sweet amenities and truly relax in your own space.
What is the best time to stay in a holiday home in Shady Side?
Pack your bags and head to your rental house in , the most popular time to visit. If smaller crowds are your thing, book a holiday home in the off-season, around , when you may get more of a bargain.
How many holiday homes are available for rent in Shady Side?
Whether you’re adventuring to Shady Side for the first time or planning a return trip to your favourite spot, pick from 643 unique holiday homes in Shady Side.
What amenities are available in a private holiday home?
You’ll often find most amenities you’re looking for, such as a private pool or hot tub, parking on the premises, a full-service kitchen or kitchenette, laundry and Wi-Fi. If your companion has four legs, book a pet-friendly Shady Side accommodation so your furry pal is as comfy and cosy as can be. Keep in mind that the price of your rental will depend on how luxe the amenities are.
Why should I book a holiday home with Wotif?
You’ll find spectacular deals, book now and pay later discounts, and a massive inventory of one-of-a-kind house rentals. Save big bucks when you book your Shady Side car hire and accommodation together into a Shady Side holiday package. Our Price Promise means that if you find a lower price online up to 24 hours before check-in, we’ll match it and refund the difference. Do the right thing and book your Shady Side holiday house with Wotif.
What are the cancellation and flexibility options?
We understand that plans change, so we offer thousands of holiday homes that have free cancellations. To be sure your rental can be cancelled for a full refund, filter your search by “free cancellation”. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.
Shady Side Holiday Homes essential information
Accommodation | 643 Holiday Homes |
---|---|
Lowest Price | AU$145 |
Highest Price | AU$505 |
Popular accommodation | Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Charming Historic Townhouse Steps From USNA, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Charming townhome with AC and WiFi in delightful Annapolis, Charming Downtown Annapolis. Stroll to all the Historic District has to offer. , Heated pool, sandy beach, pier, and playground set punch point apart!, Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Rising Sun Bay View Cottage, Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Relax on Kent Island in 3 Bedroom Home w/Waterview |
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