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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Shady Side apartments

Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is CA $371
CA $680 total
includes taxes & fees
Jun 1 - Jun 2
Waterfront Oasis of Annapolis Star
Fridge, microwave, oven, stovetop

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is CA $267
CA $665 total
includes taxes & fees
May 31 - Jun 1
Pool Loft Suite | Bay Access & Beach Passes
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Great experience"
United States
David P.
The price is CA $296
CA $557 total
includes taxes & fees
May 31 - Jun 1
18th Cent. Charm in Historic Downtown Annapolis
Exterior

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, (52 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
The price is CA $489
CA $637 total
includes taxes & fees
May 24 - May 25
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Fridge, microwave, oven, stovetop

Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy
Eastport
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is CA $411
CA $760 total
includes taxes & fees
Jun 6 - Jun 7
Annapolis Gem: Stylish and Cozy
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"The room was very clean and located conveniently to many restaurants etc. The staff was friendly. No complaints! I would definitely stay here again!"
Wendy 1-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

Find out more about Shady Side

Shady Side Apartments information

Number of reviews
150
Accommodation
79 Apartments
Lowest Price
CA $557
Highest Price
CA $760

Frequently asked questions

What's it like to stay at an apartment in Shady Side?
There are 15 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 top apartments in the area: Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!: Situated in Annapolis, 10.6 mi/17 km from the heart of Shady Side. Includes free WiFi, private balconies, and Smart TVs. Harbor View Suite Talbot County License Number STRN-25-58: Located 16.4 mi/26.3 km away in St. Michaels. Amenities include free WiFi. Access to onsite laundry facilities is available on site. New Loft w/South River view from treehouse deck!: It's situated in Riva, 8.8 mi/14.1 km away. Includes free WiFi, premium mattresses, and Smart TVs. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids: Located 9.6 mi/15.4 km away in Annapolis. Private patios and fireplaces are included. Access to onsite laundry facilities 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?
Northern Chesapeake Bay and 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 Shadyside Park 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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