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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Shady Side apartments

Outdoor pool, a heated pool

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AED 760
AED 1,520 total
includes taxes & fees
16 Jan - 17 Jan
Waterfront Oasis of Annapolis Star
Fridge, microwave, oven, stovetop

Apartment in Cape Saint Claire

Luxury Pool Loft sleeps 4
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 AED 533
AED 1,533 total
includes taxes & fees
27 Jan - 28 Jan
Luxury Pool Loft sleeps 4
Exterior detail

Apartment in Historic District

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
9.6 out of 10, Exceptional, (27 reviews)
"Very nice place, just two of us stayed but would fit 4 comfortably. "
United States
Brad L.
The price is AED 643
AED 1,193 total
includes taxes & fees
18 Jan - 19 Jan
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Fridge, microwave, oven, stovetop

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is AED 909
AED 1,778 total
includes taxes & fees
16 Jan - 17 Jan
Annapolis Gem: Stylish and Cozy
Smart TV

Apartment in Annapolis

Five Star Charmer! Great Location Downtown & Stadium! Parking too!
9.6 out of 10, Exceptional, (5 reviews)
"Jennifer met us at check in, ensured we had what we needed. Well appointed, assigned parking, coffee, water and snacks for the late night munchies. Had a great time, will return - thanks ! "
United States
Darcy W.
The price is AED 661
AED 1,210 total
includes taxes & fees
15 Feb - 16 Feb
Five Star Charmer! Great Location Downtown & Stadium! Parking too!
Exterior

Apartment in Admiral Heights

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (48 reviews)
"Convenient location, very clean, beautiful yard for a pet friendly visit. We had a great time! Would go back again. "
United States
Jackie C.
The price is AED 1,306
AED 1,702 total
includes taxes & fees
28 Jan - 29 Jan
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Dining

Apartment in Upper Marlboro

Charming 3-bedroom in Upper Marlboro - Minutes from Washington, DC
The price is AED 324
AED 449 total
includes taxes & fees
18 Jan - 19 Jan
Charming 3-bedroom in Upper Marlboro - Minutes from Washington, DC
Property grounds

Apartment in Historic District

Charming Downtown 3rd Floor 1 Bedroom Apt
9.8 out of 10, Exceptional, (20 reviews)
"We had a great time staying that this home. It was a perfect stay for my wife and I."
United States
Eric S.
The price is AED 624
AED 1,110 total
includes taxes & fees
18 Jan - 19 Jan
Charming Downtown 3rd Floor 1 Bedroom Apt
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
"Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future. "
Amanda 4-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What's it like to stay at an apartment in Shady Side?
There are 14 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: Modern Flat in the Heart of St. Michaels – Walk Everywhere: Located in St. Michaels, 16 mi/25.7 km from the heart of Shady Side. Includes private balconies and fireplaces. Access to onsite laundry facilities is available on site. Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis: Located 12.2 mi/19.7 km away in Annapolis. Free WiFi, sofa beds, and jetted bathtubs are included. Onsite laundry facilities and a hot tub are on site. Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!: 10.6 mi/17 km away in Annapolis. Free WiFi, private balconies, and Smart TVs are included. Pristine Downtown 1-Bedroom Steps from State House: Located in Annapolis, 9.6 mi/15.4 km from Shady Side. Includes free WiFi, sofa beds, and Smart TVs. 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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