Sherwood, MD

Travel Guide

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
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! (32 reviews)
Relaxing waterfront family reunion
"The Chesapeake Mansion was even better than it looks on the VRBO listing. Huge house but still managed to feel warm and inviting, never cold or stand-offish. We cooked big dinners for our group of 12 and the kitchen was perfect for that. Billiards room was fun, amazing bar room, also an exercise ..."

Reviewed on 30 March 2025

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Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
The price is AED 531 per night from Apr 16 to Apr 17
AED 531
AED 730 total
includes taxes & fees
16 Apr - 17 Apr
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! (1,707 reviews)
"Historic Property."

Reviewed on 1 April 2025

Historic Inns of Annapolis
The Westin Annapolis
The Westin Annapolis
4 out of 5
100 Westgate Cir, Annapolis, MD
The price is AED 547 per night from Apr 7 to Apr 8
AED 547
AED 624 total
includes taxes & fees
7 Apr - 8 Apr
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,001 reviews)
"Always love our Westin Annapolis stay - can’t wait to see it post construction"

Reviewed on 2 April 2025

The Westin Annapolis
See all 1,132 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.
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
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! (32 reviews)
Relaxing waterfront family reunion
"The Chesapeake Mansion was even better than it looks on the VRBO listing. Huge house but still managed to feel warm and inviting, never cold or stand-offish. We cooked big dinners for our group of 12 and the kitchen was perfect for that. Billiards room was fun, amazing bar room, also an exercise ..."

Reviewed on 30 March 2025

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and patios. Popular attractions John Smith House and Annapolis ...
10/10 Exceptional! (192 reviews)
Exceeded Our Expectations
"We loved our visit to Annapolis, and our stay at 10 Randall was all that we’d imagined it would be.We wish the weather has been a tad warmer, but I don’t think John could have fixed that .We highly recommend this charming home."

Reviewed on 29 March 2025

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
stevensville
Book a stay at this beach vacation home in Stevensville. Enjoy free WiFi, a beach locale, and private hot tubs. Our guests praise the helpful staff in our reviews. ...
10/10 Exceptional! (169 reviews)
Wonderful Get-Away
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again!"

Reviewed on 21 January 2025

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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.

Popular places to visit

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.

Back Creek Community Park

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.

Goat Island