Vacation Homes in Shady Side, MD
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Top Vacation Homes in Shady Side

Grace Cottage, St Michaels Walk to everything!

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

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

Fabulous 5-bedroom house with AC in charming Annapolis

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Charming Historic Annapolis Home With Two Off-street Parking Places!

Cute, Cozy 2-bedroom house near Annapolis with water access

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

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

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Top hotels in Shady Side

Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Find the Best Vacation Homes in Shady Side
Why book a vacation home in Shady Side?
Vacation homes in Shady Side make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Shady Side?
Private Shady Side rental homes range between $95 - $550 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Shady Side vacation home rentals. You might look for Shady Side rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Shady Side offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Shady Side?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Shady Side. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Shady Side hotels and vacation homes that best suit your stay. We also have deals for flights, and Shady Side car rentals. You’ll save even more when you bundle your items into a Shady Side vacation package!
How many vacation homes are available to book in Shady Side?
There are 592 rental homes in Shady Side. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Shady Side?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Shady Side Vacation Homes essential information
Accommodation | 592 Vacation Homes |
|---|---|
Lowest Price | $95 |
Highest Price | $550 |
Popular accommodation | Grace Cottage, St Michaels Walk to everything!, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore, Fabulous 5-bedroom house with AC in charming Annapolis, Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything, Charming Historic Annapolis Home With Two Off-street Parking Places!, Cute, Cozy 2-bedroom house near Annapolis with water access, Lovely bay views with kayaks, bikes, fire pit, crabbing & more, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view, Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Peaceful Pet-Friendly Stay - Near USNA and Beaches |
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