Shady Side Vacation Homes

Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky

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Our top choices for Shady Side holiday homes

Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

HK$4,446 total

includes taxes & fees

16 Jun - 17 Jun

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."

Brian

HK$2,480 total

includes taxes & fees

1 Jun - 2 Jun

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

Luccas C.

HK$2,472 total

includes taxes & fees

3 Jun - 4 Jun

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

Kevin F.

HK$3,280 total

includes taxes & fees

1 Jun - 2 Jun

Large 2 bedroom house with private parking in a nice neighborhood

Arnold

Traci L.

HK$2,483 total

includes taxes & fees

1 Jun - 2 Jun

Walk to Beach! King Bed & Free Beach Passes

North Beach

Kimberly F.

HK$3,312 total

includes taxes & fees

1 Jun - 2 Jun

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Becky S.

HK$5,704 total

includes taxes & fees

11 Jun - 12 Jun

WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

Jill C.

HK$5,152 total

includes taxes & fees

3 Jun - 4 Jun

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Top Shady Side Hotel Reviews

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent

"I recently stayed at La Quinta Hotel and overall had a positive experience. I checked in late & as I inspected the room, I noticed there was a leak coming from the sink. I reported the issue to the front desk & he was very understanding, informing me that since it was late, maintenance would come by the following morning to repair it. Although I did have to follow up with the front desk the next day, I was satisfied that within about 10 minutes, maintenance arrived & fixed the leak without me having to change rooms. I especially want to recognize the front desk night auditor for taking my concern seriously, not disregarding my complaint & handling the situation professionally & respectfully."

Historic Inns of Annapolis

4/10 Poor

"There were numerous communication issues between me and the staff and managers at one point our room got up to 77° and stayed like that for hours because there was no one on staffed correct the issue although we got the historic room fee waved. I don’t believe that the staff truly cared about our experience in the hotel as a whole considering that it was where we were staying to get married. I wrote an email to management at 8:30 AM and it has now been 12 hours and I have yet to get a phone call back nor an email back from anybody at this hotel. I’m extremely disappointed to say the least."

DoubleTree by Hilton Hotel Largo/Washington DC

2/10 Terrible

"Unfortunately, our stay was not a good experience due to the condition of the hotel. The AC was not working properly, and the room smelled like there had been ongoing water leakage or moisture issues. The beds were also very uncomfortable and felt as if you would roll toward the middle. That being said, the hotel staff was very nice, welcoming, and helpful throughout our stay. The manager was also kind enough to reimburse 2 of our 4 nights, which we truly appreciated. I just wish Hilton would invest in updating this property because it definitely needs renovations and better upkeep."

Comfort Inn Conference Center

8/10 Good

"Upon checking in the person checking my mother-in-law in was very rude, had an attitude, and didn’t speak or welcome us. That was a turn off after traveling for hour's!! Everything else was great!! The room was clean and the bed was comfortable. I’m not sure if I would stay there again because of the lady who was rude with the blue hair.. She needs a class on customer service for sure!!!"

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