A river with boats, a marina, and a town with houses and buildings.

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Check prices for these dates

Tonight
7 Oct - 8 Oct
Tomorrow
8 Oct - 9 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct
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Top Shady Side Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Only complaint was no coffee or cups. And lightbulbs were out."
Perry 1-night trip
Posted 15 hours ago
Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"This was a nice spot to land while we visited Annapolis family and friends. Comfortable and very nice staff - especially in the dining room!"
Virginia 2-night trip
Posted 16 hours ago
DoubleTree by Hilton Hotel Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"The views were fantastic."
Kathleen K 6-night trip
Posted 16 hours ago
Rod 'N' Reel Resort
Comfort Inn Conference Center

Comfort Inn Conference Center

8/10 Good
"Such friendly and attentive staff! Clean, no-frills room!"
LeiMeredith 1-night trip
Posted 20 hours ago
Comfort Inn Conference Center
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"my cozy room pet friendly staff"
victoria 3-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Largo/Washington DC
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Staff was great, hotel needs real renovation seems like they've done a lot of patch work. Parking should be complimentary for people staying in the hotel or a discounted rate. $35 a day for parking at the hotel you're staying at is crazy. There's very limited parking to begin with."
Lauren 2-night trip
Posted 2 days ago
Hilton Garden Inn Annapolis Downtown
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 6 days ago
St Michaels Inn
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

10/10 Excellent
"We recently stayed at Shady Side and had a great experience start to end. Communication was 10/10 and the property was as described. You could tell the hosts thought about the little details. The rental was ideal for two families with a dedicated upstairs with two bedrooms and a bathroom and the a primary bedroom downstairs with a bathroom. As a pet parent, I particularly appreciated the fenced in yard and lots of areas in the community for walking. Would definitely recommend!"
Cassandra T. 2-night trip
Posted 2 weeks ago
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

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