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Cozy place close to the city dock
Beach
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
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
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, (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
Property grounds
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
1 bedroom, iron/ironing board, free WiFi, bed sheets
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
Point of interest
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
Fridge, microwave, oven, stovetop
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 HK$1,400
HK$2,438 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
Fridge, microwave, oven, stovetop
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
Fridge, microwave, oven, stovetop
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
Property grounds
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 HK$1,182
HK$2,154 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
Fridge, microwave, oven, stovetop
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 HK$1,711
HK$2,837 total
includes taxes & fees
24 Nov - 25 Nov
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
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
Guest Quarters at the Inn - 103
Iron/ironing board, free WiFi, bed sheets
Guest Quarters at the Inn - 103
9.8 out of 10, Exceptional, (22)
"Loved front porch"
Guest Quarters at the Inn - 103
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
Annapolis Coastal Gem w/ Hot Tub, Dock, Close to Everything & Sleeps 5
Outdoor dining
Annapolis Coastal Gem w/ Hot Tub, Dock, Close to Everything & Sleeps 5
10.0 out of 10, Exceptional, (11)
"We had a wonderful experience staying at Dawn's beautiful waterfront place, which is very close to restaurants, shops, and DTA. She is a conscientious and responsive host. The place itself is like new, clean, cozy and well stocked. We slept great, which is a big + for a STR. We had fun hanging out at the bar, playing pool and watching TV. We also enjoyed getting in the hot tub (spa towels are A+) and sitting around the fire pit at night. Highly recommend. We've already booked it for our next...
The price is HK$1,936
HK$2,518 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
Point of interest
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
Point of interest
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
Outdoor pool, a heated pool
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 HK$1,787
HK$3,429 total
includes taxes & fees
8 Dec - 9 Dec
Waterfront Oasis of Annapolis Star
Anchor's Away in the Heart of Eastport!
Fridge, microwave, oven, stovetop
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!
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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (20)
"Our annual girls weekend was held at this property. The house was perfect. there were enough beds and Comfortable relaxing places to sit and view the lake relax around the pool Or just sit quietly and read a book. The property manager, Erin Was so helpful through the entire process And I do think the pictures did not do justice to the lovely appointed decor. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
Miscellaneous
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
Outdoor dining
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 hotels and other accommodation options in Shady Side. Though there aren’t many apartments, we can help you locate accommodation with similar amenities. When you search on Expedia, you can use the filters to search for a kitchen— just one of the conveniences you might find in an apartment. You can also search for similar property types like condos, holiday homes or cottages.
Are you interested in apartments over traditional hotel rooms?
Often more spacious than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your 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 best apartment for my stay in Shady Side?
Below are some of the top apartments in the area: Cozy place close to the city dock: Located 10.6 mi/17 km away in Annapolis . Free WiFi and a balcony are included . Indulge or be still near Naval Academy/ Annapolis: Located in Annapolis , 6.3 mi/10.2 km away. Includes free WiFi, a patio and a Smart TV . Access to 1 hot tub is available on site . Waterfront Oasis of Annapolis Star: Located 12 mi/19.3 km away in Annapolis . A private pool, free WiFi and a fireplace are included . An outdoor pool and a water park are on site . Anchor’s Away in the Heart of Eastport!: It’s located in Annapolis , 9.1 mi/14.6 km from Shady Side. Includes free WiFi and a Smart TV .
What will the weather be like when I travel to Shady Side?
Although weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Shady Side. The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Shady Side is 1307 mm.
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 wider 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) away. Otherwise, look 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.