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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Shady Side apartments

A house with a yellow door and a window with a lamp outside.

1. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is CA $193
CA $453 total
includes taxes & fees
Nov 15 - Nov 16
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A kitchen with wooden cabinets, granite countertops, and a dining table set with blue and white dishes.

2. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
9.0 out of 10, Wonderful, (4 reviews)
"A nice, clean, roomy place at a good price--gotta love that. The walk-out basement apartment was located in a compound of units on a quiet dead-end street. This unit is actually toward the back and I spent a little time searching for it. Once there, access to the key and apartment was no problem.The home was well-stocked with kitchen and bathroom supplies, and bedding. Would definitely stay there again."
United States
Rob L.
The price is CA $314
CA $736 total
includes taxes & fees
Nov 9 - Nov 10
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A living room with a beige sofa, two framed floral pictures, a wooden cabinet, and a small table with a lamp.

3. Cozy 1-bedroom studio in pleasant Crofton with AC

Cozy 1-bedroom studio in pleasant Crofton with AC
Crofton
9.0 out of 10, Wonderful, (2 reviews)
"Host was very friendly and accommodating. The location is wonderful. Lots of shops and festivities nearby could not have asked for better. Her cat was also very friendly "
United States
Michaela C.
The price is CA $151
CA $191 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 1-bedroom studio in pleasant Crofton with AC
Stylish kitchen with open layout and island seating

4. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 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 $292
CA $675 total
includes taxes & fees
Nov 9 - Nov 10
Pool Loft Suite | Bay Access & Beach Passes
A living room with a brown sofa, a glass coffee table, and a beige armchair.

5. Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"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. "
United States
Nathaniel R.
The price is CA $313
CA $645 total
includes taxes & fees
Nov 10 - Nov 11
Dean Street's Lower Deck House!
A two-story house with a covered patio, a garage, and a well-maintained lawn.

6. 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, (56 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
The price is CA $534
CA $660 total
includes taxes & fees
Nov 10 - Nov 11
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
A kitchen with a wooden countertop, a stove, and a refrigerator.

7. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (15 reviews)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
The price is CA $327
CA $543 total
includes taxes & fees
Nov 8 - Nov 9
18th Cent. Charm in Historic Downtown Annapolis
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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Learn more about Shady Side

Love dining out, parks, and museums? Get away to Shady Side!

See all hotels in Shady Side
A river with boats, a marina, and a town with houses and buildings.

Top reviews in Shady Side

A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District

10/10 Excellent

Great hotel great location. Friendly staff
Canada
Kelly
Reviewed April 29, 2026
Historic Inns of Annapolis

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: New Loft w/South River view from treehouse deck!: Situated in Riva, 8.8 mi/14.1 km from the heart of Shady Side. Includes free WiFi, private patios, and premium mattresses. Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!: Located 10.6 mi/17 km away in Annapolis. Free WiFi, private balconies, and Smart TVs are included. Downtown St. Michaels Studio – Walk to Waterfront, Dining & Shops: It's situated in St. Michaels, 16.1 mi/25.9 km away. Includes private balconies. 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.

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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