Sherwood Condo Rentals

A large brick house with a green roof, surrounded by lush gardens and trees.

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Our top choices for Sherwood condo rentals

A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

1. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

Kristen S.

HK$3,051 total

includes taxes & fees

28 Sept - 29 Sept

A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

2. Upscale Condo in Annapolis w/Private Parking

Historic District

Scott P.

HK$4,080 total

includes taxes & fees

6 Oct - 7 Oct

A living room with a dining table, two sofas, a coffee table, and a patterned rug.

3. Chapel Gate 3BR Steps to City Dock & Naval Academy

Historic District

JENNIFER E.

HK$4,045 total

includes taxes & fees

27 Sept - 28 Sept

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Top Sherwood Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Staff is extremely friendly and welcoming"

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Gorgeous hotel. I wish we had been there more than a night just to enjoy the various outdoor areas to relax. Enjoyed drinks and apps at their restaurants and had great coffee and breakfast at their market. We definitely want to go back when we have more time. We stayed in the Barn and it was just beautiful and quiet."

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