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Compare 61 Apartments in Shady Side with updated reviews, rates, and availability.

Spectacular Location: State Circle Apartment
Exterior

Spectacular Location: State Circle Apartment

10.0 out of 10, Exceptional, (11)
"Great location around the corner from our Thanksgiving celebration. "
Spectacular Location: State Circle Apartment
Guest quarters at the inn - 205
Exterior

Guest quarters at the inn - 205

9.4 out of 10, Exceptional, (12)
"The property was not only as described, but better than described, honestly words don’t do it justice. It was exactly what my best friend and I needed to get ready for a friends wedding, and have a comfortable place to stay for the weekend. We loved the classy decor, full length, mirror, soaking tub, and the big thank you for the welcome tray of snacks! The location is perfect, a block from the water, close to bars and restaurants, while being in a quiet neighborhood, and it’s proximity to...
Guest quarters at the inn - 205
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, (29)
"We enjoyed our stay at this prime location. First level floor was nicely equipped and had a lovely layout. Loved the historic finishes and charm of the place. Parking lot was a few blocks away near the private college."
Cozy 1st Floor King George one bedroom apartment right across from USNA
Pristine Downtown 1-Bedroom Steps from State House
Steps from the Maryland state house

Pristine Downtown 1-Bedroom Steps from State House

10.0 out of 10, Exceptional, (24)
"We had never visited Annapolis before, but my husband found this on VRBO, and it was everything it advertised. Super central location; steps from the state house; a very short walk to the waterfront; and not a terribly long walk to the Eastport neighborhood. The apartment is small but comfortable, and we enjoyed the nice touches like toiletries, water bottles, snacks and two splits of chilled prosecco in the fridge! Annapolis was a fun town to explore and if we go back, I’d stay here again."
Pristine Downtown 1-Bedroom Steps from State House
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
Chic Condo w/ Balcony in the Heart of Annapolis!
Living area

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
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
Waterfront Oasis of Annapolis Star
Waterfront Oasis of Annapolis pool grandeur.

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (72)
"We had an amazing time! Beth and Andy are wonderful hosts! We are looking forward to another stay!"
The price is AED 845
AED 1,620 total
includes taxes & fees
12 Jan - 13 Jan
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!
Cozy place close to the city dock
Room

Cozy place close to the city dock

9.8 out of 10, Exceptional, (68)
"Meet my son in Annapolis to attend the Military Bowl. Location was great, near the stadium and also close to downtown. Great place to stay when in Annapolis."
Cozy place close to the city dock
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!
Bay View Studio Apartment
Property grounds

Bay View Studio Apartment

10.0 out of 10, Exceptional, (40)
"The apartment is much larger than it looks in the photos and the view simply can't be beat. The host is very responsive and helpful. And who doesn't love a hot tub right on the water?! Would absolutely stay here again."
Bay View Studio Apartment
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Exterior

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

10.0 out of 10, Exceptional, (33)
"The Antonelli’s are wonderful hosts. Excellent communication, treated us like guests in their home. We had a three month old infant with us and the hosts had an adorable set up before we got there.But gave us plenty of room to do our own thing. The house is located near a walking path into town. We’ll definitely stay again. "
The price is AED 1,341
AED 1,746 total
includes taxes & fees
31 Jan - 1 Feb
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Tranquility Awaits
Interior

Tranquility Awaits

10.0 out of 10, Exceptional, (14)
"It was an awesome short weekend stay for Army Navy game. Will consider staying here again for sure."
Tranquility Awaits
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Interior

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

10.0 out of 10, Exceptional, (49)
"Wonderful hosts. Beautiful property. And a spacious yet cozy place to stay. We will book again next time we visit. "
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
New Loft w/South River view from treehouse deck!

New Loft w/South River view from treehouse deck!

10.0 out of 10, Exceptional, (20)
"The loft was very clean and modern inside. We enjoyed having our meals on the deck, with a nice calming view of South River. The owner was very flexible (e.g. check-in time) and easy to communicate with. Beware that the kitchenette is small (not much room to cook if that matters to you). I personally would prefer having a firmer mattress, but others may disagree."
New Loft w/South River view from treehouse deck!
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Private kitchen

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

9.8 out of 10, Exceptional, (37)
"My husband and I stayed here with our two kids for his reunion weekend and it did not disappoint. The apartment is conveniently located right outside of Gate 1 and so close to the all of the downtown offerings. The apartment was super clean and had everything we needed for our stay. We would definitely stay here again!"
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Harbor View Suite
View of harbor 1/2 block from suite.

Harbor View Suite

10.0 out of 10, Exceptional, (19)
"Excellent!"
Harbor View Suite
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 463
AED 875 total
includes taxes & fees
13 Jan - 14 Jan
Charming Downtown 3rd Floor 1 Bedroom Apt
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
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

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Exterior

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

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

10.0 out of 10, Exceptional, (206)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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 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.