Vacation Rentals in Sherwood

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis MD

Stay at this vacation home in Annapolis. Enjoy free WiFi, laundry facilities, and patios. Popular attractions John Smith House and Tose Family Tennis Center ...

10/10 Exceptional! (246 reviews)

"The house is in a great location. It is very historic and the inside is quaint as you would expect in a historic house. The single garage is around the corner and a tight squeeze. You have to either double park in front to unload (not ideal on a busy street corner) or unload at the garage and walk ..."

Reviewed on Jun 9, 2026

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville MD

Stay at this houseboat in Stevensville. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Romancoke Wharf County Park and Matapeake ...

10/10 Exceptional! (57 reviews)

"I have stayed at many places over the years. This would be my favorite place. The view and the location was unbelievable. We were in town for a wedding and our host let us check in early to accommodate the wedding schedule. I would definitely recommend this house boat to anyone that wants a unique ..."

Reviewed on Jun 1, 2026

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Bozman MD

Stay at this cottage in Bozman. Enjoy air conditioning. Popular attractions Neavitt Park and Back Creek Park are located nearby.

See all properties in Sherwood

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.

Check Sherwood hotel availability

Stay near popular Sherwood attractions

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.

See properties