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Check prices for these dates

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12 Dec - 14 Dec
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23 Jan - 25 Jan
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Apartments in Shady Side

Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AED 760
AED 1,520 total
includes taxes & fees
1 Dec - 2 Dec
Waterfront Oasis of Annapolis Star
Interior
Dean Street's Lower Deck House!

Dean Street's Lower Deck House!

Historic District
10.0 out of 10, Exceptional, (2)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
The price is AED 699
AED 1,580 total
includes taxes & fees
28 Dec - 29 Dec
Dean Street's Lower Deck House!
Terrace/patio
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Admiral Heights
10.0 out of 10, Exceptional, (46)
"Perfect hideaway for a weekend trip to Annapolis. Great location and had everything we needed for the kids. Host was very accommodating and communicative, would come back!"
United States
Jay B.
The price is AED 1,306
AED 1,702 total
includes taxes & fees
1 Dec - 2 Dec
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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.
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Top Shady Side Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Clean rooms, comfortable beds, friendly staff."
Nancy 2-night trip
Posted 16 hours ago
Graduate by Hilton Annapolis

Frequently asked questions

What's it like to stay at an apartment in Shady Side?
There are 13 lodging options in Shady Side. Though there aren't many apartments, we can help you search for accommodations that are similar. When you search on Expedia, you can use the filters to search for conveniences you might find in an apartment such as a kitchen. You can also search for similar property types like vacation homes, condos, or cabins.
Are you thinking about an apartment for your stay?
An apartment is often more spacious than a traditional hotel room and includes a kitchen for convenient home-cooked meals. Apartments are ideal for families who want the conveniences of home but also for couples looking for something with a more local feel.
What's the top apartment for my stay in Shady Side?
Here are some of the favorite apartments in the area: Downtown St. Michaels | Porch + Pet-Friendly: Located 15.9 mi/25.6 km away in St. Michaels. Amenities include private balconies. Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis: Located in Annapolis, 12.2 mi/19.7 km away. Includes free WiFi, sofa beds, and jetted bathtubs. Onsite laundry facilities and a hot tub are on site. Modern Flat in the Heart of St. Michaels – Walk Everywhere: Located 16 mi/25.7 km away in St. Michaels. Private balconies and fireplaces are included. Access to onsite laundry facilities is available on site. Waterfront Oasis of Annapolis Star: Located in Annapolis, 12 mi/19.3 km from Shady Side. Includes a private pool, free WiFi, and fireplaces. Access to an outdoor pool is available on site.
What will the weather be like when I travel to Shady Side?
Though weather is just one factor, it can really affect your travel plans, especially if you're planning an extended stay in Shady Side. The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Shady Side is 51 inches.
What should I see and do in Shady Side?
Shadyside Park and Northern Chesapeake Bay are a couple of scenic spots to enjoy the outdoors, whereas Captain Avery Museum is one of the cultural attractions. Other places in town to visit include Chesapeake Bay and Franklin Point State Park.
What's the best way to get to and around Shady Side?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Fort Meade, MD (FME-Tipton), which is located 21.6 mi (34.8 km) from the city center. You can also search for flights into College Park, MD (CGS), which is 24.1 mi (38.7 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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