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

Charming Historic Townhouse Steps From USNA

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

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

Quiet Relaxing Waterfront Suisse Chalet

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

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

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

Cozy Annapolis Cottage

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Top hotels in Shady Side

Graduate by Hilton Annapolis
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 $104 - $343 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 654 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 | 654 Vacation Homes |
---|---|
Lowest Price | $104 |
Highest Price | $343 |
Popular accommodation | Charming Historic Townhouse Steps From USNA, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , The Cozy Crab- Your Charming Haven in Lovely North Beach!, Quiet Relaxing Waterfront Suisse Chalet, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks, The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill, Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Cozy Annapolis Cottage, Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium, Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown. |
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