Search Apartments in Shady Side

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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 78 Apartments in Shady Side with updated reviews, rates, and availability.

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!
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Fridge, microwave, oven, stovetop

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

9.8 out of 10, Exceptional, (38)
"Perfect location for walking around the Annapolis waterfront area! Clean, comfortable and well appointed. Would definitely stay here again!"
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
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
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."
The price is AED 698
AED 1,357 total
includes taxes & fees
29 May - 30 May
18th Cent. Charm in Historic Downtown Annapolis
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.
Harbor View Suite
Fridge, microwave, coffee/tea maker, toaster

Harbor View Suite

10.0 out of 10, Exceptional, (22)
"Excellent!"
Harbor View Suite
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
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
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
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
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!
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 AED 845
AED 1,620 total
includes taxes & fees
29 May - 30 May
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 AED 404
AED 706 total
includes taxes & fees
27 Jun - 28 Jun
Luxury 2-bedroom basement apartment in Bowie
Bay View Studio Apartment
Outdoor spa tub

Bay View Studio Apartment

10.0 out of 10, Exceptional, (44)
"Lovely property, larger than I expected, hot tub on the waterfront was wonderful. We will certainly be back. "
Bay View Studio Apartment
Studio in Downtown – Walk to Everything!
Iron/ironing board, WiFi, bed sheets

Studio in Downtown – Walk to Everything!

10.0 out of 10, Exceptional, (19)
"Great central location. Spotless and comfortable-a great home base for being out and about in St. Michael's."
Studio 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
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
Water view studio. 20 minutes from Annapolis.
Property grounds

Water view studio. 20 minutes from Annapolis.

10.0 out of 10, Exceptional, (1)
"Perfect for a couple weekend getaway! We were in town for sail boat demos for the weekend and found this newly renovated studio apartment above the owners garage bright and clean. With a short walk down to the beach, the beautiful sunrises will take your breath away! A must see. Will return again! Thanks Rob and Suzanne"
Water view studio. 20 minutes from Annapolis.
Guest Quarters at the Inn - 101
Iron/ironing board, free WiFi, bed sheets

Guest Quarters at the Inn - 101

9.8 out of 10, Exceptional, (12)
"We had a great stay at the Guest Quarters. The place is very clean and has recently been updated. We lucked out and hit Fist Friday in North Beach and enjoyed live music and great food just a block away."
Guest Quarters at the Inn - 101
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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Other property types in Shady Side

The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (5)
"Our stay at the house was great. The host had amazing customer service and the location is beautiful."
The price is AED 716
AED 1,399 total
includes taxes & fees
2 Jun - 3 Jun
The Cottage
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Interior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

9.8 out of 10, Exceptional, (57)
"This property is very close to the water. The views are amazing! The house is so charming and beautifully decorated with unique pieces and cultural art from around the world. It was also very well equipped with all essentials for the kitchen and bathrooms. I highly recommend it."
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (218)
"We loved our stay here! The location is unbeatable and having access to parking was very convenient. The house itself was quaint with character and very clean! My husband and I stayed with our 4 young children and had ample space. The beds were all comfy and the kitchen had everything we needed. Communication with the host was great! We really hope to stay here again in the future! "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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.

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 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. 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. Waterfront Oasis of Annapolis Star: Located in Annapolis, 12 mi/19.3 km from Shady Side. Includes a private pool, free WiFi, and fireplaces. An outdoor pool and a water park 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 London Town.
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.