Search Apartments in Shady Side

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Apartments in Shady Side

Luxury Pool Loft sleeps 4
Pool

Luxury Pool Loft sleeps 4

10.0 out of 10, Exceptional, (2)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
The price is AED 489
AED 1,344 total
includes taxes & fees
21 Oct - 22 Oct
Luxury Pool Loft sleeps 4
Annapolis Gem: Stylish and Cozy
Fridge, microwave, oven, stovetop

Annapolis Gem: Stylish and Cozy

10.0 out of 10, Exceptional, (1)
"Clean and nicely decorated. Did not realize it was a basement unit."
The price is AED 909
AED 1,782 total
includes taxes & fees
7 Oct - 8 Oct
Annapolis Gem: Stylish and Cozy
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (79)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is AED 992
AED 1,817 total
includes taxes & fees
13 Oct - 14 Oct
Waterfront Oasis of Annapolis Star
Dean Street's Lower Deck House!
Interior

Dean Street's Lower Deck House!

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. "
The price is AED 775
AED 1,671 total
includes taxes & fees
5 Oct - 6 Oct
Dean Street's Lower Deck House!
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.0 out of 10, Wonderful, (12)
"Property description is accurate, host is quickly responsive."
The price is AED 628
AED 1,265 total
includes taxes & fees
5 Oct - 6 Oct
18th Cent. Charm in Historic Downtown Annapolis
Modern 1BR Near DC – Quiet Comfort, Fast Commute
Fridge, microwave, oven, stovetop

Modern 1BR Near DC – Quiet Comfort, Fast Commute

10.0 out of 10, Exceptional, (4)
"I thoroughly enjoyed my stay. Poo"
The price is AED 349
AED 643 total
includes taxes & fees
7 Oct - 8 Oct
Modern 1BR Near DC – Quiet Comfort, Fast Commute
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Terrace/patio

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

10.0 out of 10, Exceptional, (42)
"Everything was really lovely- clean, comfortable, beautifully decorated rooms. Loved the little things like all the fresh flowers in rooms - would definitely recommend!"
The price is AED 1,561
AED 2,022 total
includes taxes & fees
20 Oct - 21 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shady Side Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Great"
BRIAN 2-night trip
Posted 4 days ago
Hilton Garden Inn Annapolis Downtown

Frequently asked questions

What's it like to stay at an apartment in Shady Side?
There are 12 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 more popular apartments in the area: Riverfront Retreat 7mil from MD Renaissance Fest!: Situated in Riva, 9 mi/14.4 km from the heart of Shady Side. 18th Cent. Charm in Historic Downtown Annapolis: Located in Annapolis, 9.5 mi/15.3 km away. Includes free WiFi, private patios, and fireplaces. Onsite laundry facilities and a game room are on site. Harbor View Suite Talbot County License Number STRN-25-58: Located in St. Michaels, 16.4 mi/26.3 km from Shady Side. Includes free WiFi. 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?
Cultural attractions include Captain Avery Museum, whereas Shadyside Park is a spot to enjoy nature. In the larger area, you'll find Franklin Point State Park and Smithsonian Environmental Research Center.
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.