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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 79 Apartments in Shady Side with updated reviews, rates, and availability.

Cozy place close to the city dock
Beach

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
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, (29)
"We really enjoyed our stay! Very peaceful and relaxing, the bed felt like lying on a cloud! It was like having a spa in your room we loved the sauna especially. We look forward to booking again. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Bay View Studio Apartment
Outdoor spa tub

Bay View Studio Apartment

10.0 out of 10, Exceptional, (42)
"Lovely property, larger than I expected, hot tub on the waterfront was wonderful. We will certainly be back. "
Bay View Studio Apartment
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
Guest quarters at the inn - 205
TV

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
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
Property grounds

HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!

9.8 out of 10, Exceptional, (16)
"What a beautiful and welcoming property! Tons of wildlife activity to view and great water views. Amenities were great. Really appreciate everything! Lovely host!"
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
St Michaels is waiting for you. Join us at CoCo's
Living area

St Michaels is waiting for you. Join us at CoCo's

St Michaels is waiting for you. Join us at CoCo's
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Fridge, microwave, oven, stovetop

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

9.6 out of 10, Exceptional, (23)
"Cleaning of the apartment needs to improve "
The price is AED 643
AED 1,193 total
includes taxes & fees
25 Mar - 26 Mar
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
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, (24)
"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
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)
"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
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)
"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
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 1,629 total
includes taxes & fees
25 Mar - 26 Mar
Waterfront Oasis of Annapolis Star
Tranquility Awaits
Property grounds

Tranquility Awaits

10.0 out of 10, Exceptional, (15)
"We absolutely loved our stay here. Everything was perfect from the communication with the owners to the cleanliness of the apartment. We could not have found a better place to stay for our trip. Perfect for kids and teens. "
Tranquility Awaits
Chesapeake Bayside Loft
Beach

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
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.8 out of 10, Exceptional, (6)
"Had a great stay, super close to everything. Jennifer was very communicative!"
The price is AED 698
AED 1,348 total
includes taxes & fees
13 Apr - 14 Apr
18th Cent. Charm in Historic Downtown Annapolis
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)
"A very good location, ten minutes from anywhere you need to go. The hosts were both welcoming and charming. "
The price is AED 1,451
AED 1,884 total
includes taxes & fees
25 Mar - 26 Mar
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Join Us In St Michaels, Book Spring/Summer Now
Iron/ironing board, WiFi, bed sheets

Join Us In St Michaels, Book Spring/Summer Now

10.0 out of 10, Exceptional, (15)
"Just back from a wonderful weekend in St Michael’s. This property was perfect for the two of us. Convenient parking, downtown location and quiet and comfortable stay. We’re hopping for another visit soon. "
Join Us In St Michaels, Book Spring/Summer Now
Cozy 1st Level Beach House - Walk Everywhere
Property grounds

Cozy 1st Level Beach House - Walk Everywhere

2.0 star property
The price is AED 415
AED 1,584 total
includes taxes & fees
26 Mar - 27 Mar
Cozy 1st Level Beach House - Walk Everywhere
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
Property grounds

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

The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (3)
"Absolutely gorgeous home! Highly recommend this property! The pictures do not do it justice. The house was impeccably clean. The two downstairs bedrooms were quite large and the loft was perfect for my teenage daughter and her friend. The property was very peaceful and quiet. The road was practically private. Owners of the property were highly responsive and checked on us during our stay. Again, highly recommend. "
The price is AED 845
AED 1,574 total
includes taxes & fees
31 Mar - 1 Apr
The Cottage
Bay views with kayaks, bikes, fire pit, crabbing and more
Fridge, microwave, oven, stovetop

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (17)
"Very clean, everything as described. Awesome host, communication an A+. Would definitely stay again, if we are in the area."
Bay views with kayaks, bikes, fire pit, crabbing and more
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, (209)
"Perfect Location - Easy Process - Comfortable Home!"
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 favorite apartments in the area: Cozy place close to the city dock: Located 10.6 mi/17 km away in Annapolis. Free WiFi and private balconies are included. Waterfront Oasis of Annapolis Star: Located in Annapolis, 12 mi/19.3 km away. Includes a private pool, free WiFi, and fireplaces. An outdoor pool and a water park are on site. Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis: Located 12.2 mi/19.7 km away in Annapolis. Free WiFi, sofa beds, and jetted bathtubs are included. A hot tub and a sauna 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.