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Compare 60 Apartments in Shady Side with updated reviews, rates, and availability.

Cozy place close to the city dock
Room
Cozy place close to the city dock
9.8 out of 10, Exceptional, (66)
"Liked everything. Perfect for what we wanted. "
Cozy place close to the city dock
Chesapeake Bayside Loft
Room
Chesapeake Bayside Loft
8.0 out of 10, Very Good, (12)
"Great property, needs some TLC in areas to really make this be an amazing property...overall it's very clean, soft beds and has a fantastic 2 min walk to the bay for coffee or a beer/ wine...quiet neighborhood, easy access...I think the owner is really miss out on the opportunity to make this home a must rent ..back yard needs some love, lights, fire pit, corn hole etc...overall, great stay, compared to DTA this is excellent "
Chesapeake Bayside Loft
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Jacuzzi Jetted Hot Tub
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
9.6 out of 10, Exceptional, (27)
"Stayed for 3 nights in this clean, quiet loft at the end of a dead end 2-lane road. *Loved the dry sauna! Nice heat! *Loft is accessed through stairs inside the garage. *Kitchenette is small but works for breakfast and basics. *Love the large closet which is sunny and like another bedroom. *Easy communication with owner and easy access. * About 10m by car to Sandy Point State Park * About 15m by car into downtown Annapolis Great base for exploring the Annapolis area."
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Tranquility Awaits
Interior
Tranquility Awaits
10.0 out of 10, Exceptional, (13)
"We stayed here for two nights and would absolutely stay here again! The space was clean, well stocked, and very comfortable. I would absolutely recommend this place for anyone staying in the area!!"
Tranquility Awaits
Guest quarters at the inn - 204
Exterior
Guest quarters at the inn - 204
9.8 out of 10, Exceptional, (12)
"Overall great place. Couple of recommendations to make it even better. First, recommend a few more trash cans in the place. Only had one in the kitchen and bathroom. Also great to have them with trash liners. Same for tissue boxes. The one in the bathroom was empty. Would have appreciated more than one soap bar too.great Recommend checking that all the appliances work. The TV in the living room would not turn on.. Also te cabinet under the sink was loose. Again all minor things. F"
Guest quarters at the inn - 204
Walk everywhere from this 1st floor dog-friendly apartment with parking, private backyard
Welcome to Below Deck, the 1st floor of this charming Eastport 2-unit building.
Walk everywhere from this 1st floor dog-friendly apartment with parking, private backyard
2.5 star property
10.0 out of 10, Exceptional, (2)
"In town for the Annapolis Sailboat Show. It was the perfect location. Easy walking distance to downtown and tons of bars and restaurants. Property manager is quick to respond to communication, and was extremely helpful returning a lost item. The property is very nicely updated and was extremely comfortable. It had absolutely everything we needed in the perfect spot!"
Walk everywhere from this 1st floor dog-friendly apartment with parking, private backyard
Cozy 1st Floor King George one bedroom apartment right across from USNA
Exterior detail
Cozy 1st Floor King George one bedroom apartment right across from USNA
10.0 out of 10, Exceptional, (27)
"Always a great stay. Close to everything, from shops to restaurants and bars. Can’t wait to go back "
The price is AED 661
AED 1,151 total
includes taxes & fees
24 Nov - 25 Nov
Cozy 1st Floor King George one bedroom apartment right across from USNA
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Private kitchen
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
10.0 out of 10, Exceptional, (34)
"Had a wonderful time here in the fall of 2024."
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Coastal Kent Narrows Home on Bay
Living area
Coastal Kent Narrows Home on Bay
9.4 out of 10, Exceptional, (9)
"This place is a fantastic place to stay. Brandon was very responsive to any emails or questions sent to him. The place is very clean and tidy, very easy to get in and out of. We would definitely recommend this property to anybody. We will certainly be booking it again. "
Coastal Kent Narrows Home on Bay
Charming Downtown 3rd Floor 1 Bedroom Apt
The bedroom with a queen sized bed.
Charming Downtown 3rd Floor 1 Bedroom Apt
9.8 out of 10, Exceptional, (18)
"Great location for place to stay during weekend when you need convenient accommodation "
The price is AED 558
AED 1,017 total
includes taxes & fees
1 Dec - 2 Dec
Charming Downtown 3rd Floor 1 Bedroom Apt
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Larger of the 2 bedrooms, with a queen bed and sitting area
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
9.6 out of 10, Exceptional, (22)
"Being able to walk down the sidewalk to the Visitor's Entrance at the USNA meant we got to maximize our time with our plebe. The best part about this location was we didn't have to stress over the traffic and parking situation at all (and the traffic was a lot!). We got to walk back with him each evening and on Sunday morning he was able to walk over to us when he was released. The second best part was while he was catching up with family and friends on his phone or just enjoying the peace...
The price is AED 808
AED 1,340 total
includes taxes & fees
24 Nov - 25 Nov
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Guest Quarters at the Inn - 101
Exterior
Guest Quarters at the Inn - 101
9.8 out of 10, Exceptional, (12)
"This property is right in the Main Street running through Chesapeake Beach and North Beach. It's close to the beaches, restaurants, and close to all of the local attractions. The room itself was large, clean, and comfortable, and the building was both quiet, secure, and well kept. We'll definitely be back!"
Guest Quarters at the Inn - 101
Guest Quarters at the Inn - 103
Exterior
Guest Quarters at the Inn - 103
9.8 out of 10, Exceptional, (22)
"Loved front porch"
Guest Quarters at the Inn - 103
Charming Eastport
Living area
Charming Eastport
9.4 out of 10, Exceptional, (3)
"This was a charming apartment nestled in the quiet side of annapolis. Everything was within walking distance. The apartment had everything you needed if you wanted to cook. Just bring your food!"
Charming Eastport
Annapolis Coastal Gem w/ Hot Tub, Dock, Close to Everything & Sleeps 5
Main room lounge area. Sectional has a new pull out sofa bed (double).
Annapolis Coastal Gem w/ Hot Tub, Dock, Close to Everything & Sleeps 5
10.0 out of 10, Exceptional, (11)
"This was the perfect place to stay for a weekend visit with my Midshipman! Quiet area, very clean accommodations, well equipped with anything you would need during your stay, and close to DTA. My Mid and I were able to spend time together relaxing, and have a few of her fellow midshipmen join us for dinner, playing pool and hanging out in the hot tub. Dawn & Randy have thought of everything for their guests and are amazing hosts! "
The price is AED 915
AED 1,189 total
includes taxes & fees
2 Dec - 3 Dec
Annapolis Coastal Gem w/ Hot Tub, Dock, Close to Everything & Sleeps 5
Stay in the heart of Historic Annapolis 2 blocks from Main Street
The King corner bedroom has views of the Annapolis cobblestone streets.
Stay in the heart of Historic Annapolis 2 blocks from Main Street
2.0 star property
10.0 out of 10, Exceptional, (3)
"Excellent"
Stay in the heart of Historic Annapolis 2 blocks from Main Street
Steps to marinas from 2nd floor apartment with parking, private balcony
Welcome to Above Deck - the 2nd floor apartment of this charming Eastport 2-unit building.
Steps to marinas from 2nd floor apartment with parking, private balcony
2.0 star property
10.0 out of 10, Exceptional, (2)
Steps to marinas from 2nd floor apartment with parking, private balcony
Waterfront Oasis of Annapolis Star
Waterfront Oasis of Annapolis pool grandeur.
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (71)
"We had an amazing time! Beth and Andy are wonderful hosts! We are looking forward to another stay!"
The price is AED 845
AED 1,629 total
includes taxes & fees
18 Nov - 19 Nov
Waterfront Oasis of Annapolis Star
Anchor's Away in the Heart of Eastport!
Living area
Anchor's Away in the Heart of Eastport!
9.8 out of 10, Exceptional, (37)
"We really enjoyed the location and Eastport. "
Anchor's Away in the Heart of Eastport!
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
Terrace/patio
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
10.0 out of 10, Exceptional, (27)
"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!
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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
Private rear courtyard
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from Gate One & Steps from the Waterfront
Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
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 16 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 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?
Shadyside Park and Franklin Point State Park are a couple of scenic spots to enjoy the outdoors, whereas Captain Avery Museum is one of the cultural attractions. In the larger area, you’ll find London Town and Maryland Quiet Waters 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.