Sherwood
Travel Guide
Visit Sherwood
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Aug 10 to Aug 11
CA $141
CA $207 total
Aug 10 - Aug 11
includes taxes & fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,811 reviews)
"Enjoyed the stay! Beautiful place!"
Reviewed on Jul. 28, 2025
Graduate by Hilton Annapolis
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $214 per night from Aug 10 to Aug 11
CA $214
CA $244 total
Aug 10 - Aug 11
includes taxes & fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.2/10 Wonderful! (1,000 reviews)
First class
"It was pouring when we arrived, my wife and i were soaked and the staff was at the front desk with warm towels. Beginning to end first class service, attentiveness and respectful."
Reviewed on Jul. 28, 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Aug 10 to Aug 11
CA $138
CA $158 total
Aug 10 - Aug 11
includes taxes & fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.4/10 Very Good! (1,001 reviews)
7 out of 10 stars
"The hotel is older and as we walked through we were saying how it could be (& you can tell it was) a really nice hotel. Don’t misunderstand, it was a nice hotel, but you can tell it’s ‘used’. There are scuffs on doors and walls, there are tiles broken on floors, etc. the room itself was clean. The ..."
Reviewed on Jul. 27, 2025
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.
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sherwood
Book a stay at this family-friendly vacation home in Sherwood. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Goat Island and Back ...
10/10 Exceptional! (33 reviews)
Beautiful home and tons of space
"This is a beautiful property, well appointed, but not too formal for families wanting to be in the pool or on the water all day. We were a party of 12 including six grandchildren. There was plenty to do for the adults and the grandchildren and plenty of space in the home to not feel like you were ..."
Reviewed on Jul. 9, 2025
Floating 2 bed 2 bath condo stunning views of the bay
Stevensville
Stay at this houseboat in Stevensville. Enjoy a beach locale and an in-room coffeemaker. Popular attractions Matapeake State Park and Romancoke Wharf County ...
8/10 Very Good! (4 reviews)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby."
Reviewed on Jun. 7, 2025
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Port Republic
Book a stay at this beach cabin in Port Republic. Enjoy free WiFi, a beach locale, and a garden. Popular attractions CSA Park and R&J's PlayPark are located ...
9.8/10 Exceptional! (174 reviews)
Peace and serenity
"First, Brett is an exceptional host. Very helpful and responsive. This is a very special place in a wonderful community with incredible views. Rustic, warm and the perfect place to relax. We didn’t want to leave! Highly recommend."
Reviewed on Jul. 25, 2025
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.
Popular places to visit
Goat Island
Commune with nature and explore the great outdoors at Goat Island during your travels in Sherwood. Wander the marina or discover the area's sunsets.
Back Creek Community Park
Back Creek Community Park is just one of the places to see in Sherwood, so why not enjoy the other things to explore during your travels? Wander the marina or discover the area's sunsets.