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

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Check prices for these dates

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct
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Top Shady Side Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Clean room, very nice decor and great staff"
Nadine 2-night trip
Posted 3 hours ago
Graduate by Hilton Annapolis
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

8/10 Good
"Upon checking inn we decided we did not want to be looking at the dumpster the whole weekend so asked for the interstate view They were very accommodating easy going and made that happen No complaints about thr stay very comfy basic for a 2day weekend very close to ALOT of attractions"
Dee 2-night trip
Posted 3 hours ago
Comfort Inn Largo-Washington DC East
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"First time staying at the resort. We stayed two nights to celebrate my wife's birthday. I had ordered flowers that were delivered before our arrival and frontbdesk had them delivered to our room. The views from the waterfront tower build were amazing. The entire resort is very clean and well maintained. Good choice of restaurants/bars on site. Other restaurants are walkable or a short drive. The casino was surprisingly quiet and very clean, relaxing way to pass some time and maybe win some money. Enjoyed walking though the railroad museum that is on site as well. Everyone on this property were friendly and helpful. Will definitely return!"
James 2-night trip
Posted 3 hours ago
Rod 'N' Reel Resort
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."
Lamont 3-night trip
Posted 23 hours ago
The Inn at Chesapeake Bay Beach Club
Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent
"Clean, we'll maintained. Staffers friendly but professional A great stay"
Matt 3-night trip
Posted 1 day ago
Microtel Inn & Suites by Wyndham Gambrills/Odenton
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Perfect place to stay! Classy. Clean comfortable amazing staff"
Nila 2-night trip
Posted 2 days ago
Annapolis Waterfront Hotel, Autograph Collection
St Michaels Inn

St Michaels Inn

10/10 Excellent
"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."
Mary 1-night trip
Posted 4 days ago
St Michaels Inn
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Shalinda was the most welcoming front desk staff i have ever encountered."
Dennis 5-night trip
Posted 5 days ago
Sonesta ES Suites Annapolis
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

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

10/10 Excellent
"Great quaint house in Shady Side. Chris and Mary have been great and attentive hosts."
Bastian S. 7-night trip
Posted 3 weeks ago
Lovely bay views with kayaks, bikes, fire pit, crabbing & more