Search Apartments in Shady Side

    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

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Apartments in Shady Side

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Beach

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

9.8 out of 10, Exceptional, (69)
"Great location, comfortable stay!!"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
The heart of St Michaels awaits.
Exterior

The heart of St Michaels awaits.

10.0 out of 10, Exceptional, (37)
"This flat/apartment is perfect, exactly as described. Located in the heart of town, convenient to all restaurants and shops. The flat beautifully updated and appointed, and spotlessly clean. We were extremely comfortable and will definitely return."
The heart of St Michaels awaits.
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.6 out of 10, Exceptional, (7)
"Property description is accurate, host is quickly responsive."
18th Cent. Charm in Historic Downtown Annapolis
Guest Quarters at the Inn - 102
1 bedroom, iron/ironing board, free WiFi, bed sheets

Guest Quarters at the Inn - 102

9.8 out of 10, Exceptional, (18)
"Close to many restaurants and activities "
Guest Quarters at the Inn - 102
Harbor View Suite
Fridge, microwave, coffee/tea maker, toaster

Harbor View Suite

10.0 out of 10, Exceptional, (22)
"Excellent!"
Harbor View Suite
Pristine Downtown 1-Bedroom Steps from State House
Fridge, microwave, oven, stovetop

Pristine Downtown 1-Bedroom Steps from State House

10.0 out of 10, Exceptional, (25)
"Perfect location to downtown Annapolis; lovely, clean, and comfortable space. Owners make the stay enjoyable and easyy to navigate. "
Pristine Downtown 1-Bedroom Steps from State House
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Interior

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

9.6 out of 10, Exceptional, (30)
"Perfect place to go and relax and get away from the world. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Apartment in Downtown – Walk to Everything!
Living area

Apartment in Downtown – Walk to Everything!

9.0 out of 10, Wonderful, (2)
"We loved the property and the location (can’t be beat!). We walked to shops, restaurants, and bars all over town. It also had convenient parking. The apartment was clean and had everything we needed for a short stay. "
Apartment in Downtown – Walk to Everything!
Tranquility Awaits
Property grounds

Tranquility Awaits

10.0 out of 10, Exceptional, (18)
"It was an awesome short weekend stay for Army Navy game. Will consider staying here again for sure."
Tranquility Awaits
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
Property grounds

Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!

10.0 out of 10, Exceptional, (31)
"Well decorated and comfortable stay. Very quiet and great place to sit and enjoy the sunrise/sunset."
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
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, (34)
"We stayed for the Annapolis 10-miler and it was a great location for runners and spectators! "
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Walk everywhere from 1st floor dog-friendly apartment with parking and backyard
Fridge, microwave, oven, stovetop

Walk everywhere from 1st floor dog-friendly apartment with parking and backyard

2.5 star property
10.0 out of 10, Exceptional, (2)
"This tastefully decorated apartment is in a perfect location to enjoy all that is Annapolis. "
Walk everywhere from 1st floor dog-friendly apartment with parking and backyard
Chic Condo w/ Balcony in the Heart of Annapolis!
Interior

Chic Condo w/ Balcony in the Heart of Annapolis!

3.0 star property
8.0 out of 10, Very Good, (1)
Chic Condo w/ Balcony in the Heart of Annapolis!
Guest quarters at the inn - 205
TV

Guest quarters at the inn - 205

9.4 out of 10, Exceptional, (12)
"Great stay"
Guest quarters at the inn - 205
Charming Eastport
Aerial view

Charming Eastport

9.4 out of 10, Exceptional, (3)
"We thoroughly enjoyed this section of Eastport. The views of the marina were beautiful and we found a couple new restaurants nearby! Excellent communication with the owners."
Charming Eastport
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is SAR 911
SAR 1,727 total
includes taxes & fees
6 Jun - 7 Jun
Waterfront Oasis of Annapolis Star
Luxury 2-bedroom basement apartment in Bowie
2 bedrooms, in-room safe, desk, iron/ironing board

Luxury 2-bedroom basement apartment in Bowie

10.0 out of 10, Exceptional, (1)
"We had a nice stay at this location. The apartment is comfortable and cozy. Would definitely stay here again."
The price is SAR 413
SAR 763 total
includes taxes & fees
27 Jun - 28 Jun
Luxury 2-bedroom basement apartment in Bowie
Charming apt in the heart of Eastport & Annapolis
Aerial view

Charming apt in the heart of Eastport & Annapolis

Charming apt in the heart of Eastport & Annapolis
Cozy 1st Floor King George one bedroom apartment right across from USNA
Fridge, microwave, oven, stovetop

Cozy 1st Floor King George one bedroom apartment right across from USNA

10.0 out of 10, Exceptional, (29)
"We were thrilled to be able to return to this great apartment.It is very close to Gate 1 and the sofa bed has a great mattress on it!We hope to continue to return to this rental."
Cozy 1st Floor King George one bedroom apartment right across from USNA
Pet-Friendly Studio in Bowie: 9 Mi to Six Flags
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

Pet-Friendly Studio in Bowie: 9 Mi to Six Flags

2.0 star property
Pet-Friendly Studio in Bowie: 9 Mi to Six Flags
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 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 and private balconies. The heart of St Michaels awaits.: 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 12 mi/19.3 km away in Annapolis. A private pool, free WiFi, and fireplaces are included. An outdoor pool and a water park are on site. 18th Cent. Charm in Historic Downtown Annapolis: Located in Annapolis, 9.5 mi/15.3 km from Shady Side. Includes free WiFi, private patios, and fireplaces. Onsite laundry facilities and a game room are 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 Triton Beach.
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.