Sherwood, MD

Travel Guide

A large brick house with a green roof, surrounded by lush gardens and trees.
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road Sherwood MD
$150 nightly
The price is $165 total per night from Sep 20 to Sep 21
$165 total
Sep 20 - Sep 21
Total with taxes and fees
Stay at this hotel in Sherwood. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Knapp's Narrows Marina & Inn and Back Creek Community ...
Knapps Narrows Marina & Inn
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$83 nightly
The price is $95 total per night from Sep 27 to Sep 28
$95 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.8/10 Excellent! (1,178 reviews)
"Would not stay here again"

Reviewed on Sep 16, 2026

DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$140 nightly
The price is $159 total per night from Oct 12 to Oct 13
$159 total
Oct 12 - Oct 13
Total with taxes and 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 ...
9/10 Wonderful! (2,001 reviews)
"Every thing was amazing. The staff was extremely helpful and the parking situation was perfect. Room was top notch."

Reviewed on Sep 16, 2026

Historic Inns of Annapolis
See all 1,169 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 MD
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 ...
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Annapolis City Dock and Bay Ridge Beach are ...
9.6/10 Exceptional! (19 reviews)
"We had a lovely stay at this charming cottage on the bay. Everything was well maintained, the host provided strong communication, the grounds are beautiful, and our family found the hot tub to be a wonderful place to both relax amidst nature and reconnect . Also our 2 little dogs felt very much at ..."

Reviewed on Aug 3, 2026

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina ...
9.6/10 Exceptional! (134 reviews)
"Location was perfect and we enjoyed the sunrise every morning. Walkable to everything in St. Michael’s. Beautiful historic home and furnishings. A great stay!!"

Reviewed on Aug 24, 2026

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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.

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.
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Frequently asked questions

Is Sherwood worth visiting?
Sherwood is worth visiting for its diverse culinary scene, where travelers can enjoy Latin American and Asian dining. The destination also offers standout attractions like Goat Island and outdoor experiences at Back Creek Community Park, providing a mix of natural beauty and recreational opportunities.
When is the best time to visit Sherwood?
The best time to visit Sherwood is from March through May, when the weather is typically mild and pleasant. For fewer crowds and better value, the quieter months of December through February are a good option, offering cooler temperatures and a more relaxed experience for travelers.
What is Sherwood known for?
Sherwood is known for places like Goat Island and Back Creek Community Park, which offer travelers opportunities to enjoy the outdoors. The destination also features a Latin American food culture, providing a variety of culinary experiences to discover.
What is a good itinerary length for Sherwood?
A good itinerary length for Sherwood is one to two days to explore natural spots like Goat Island and Back Creek Community Park. For a more relaxed trip, two to three days allows travelers to enjoy these areas at a slower pace and try the local Latin American, Asian, and Italian cuisines.
What are the top things to do in and around Sherwood?
In Sherwood, travelers can enjoy natural outdoor spaces such as Goat Island and Back Creek Community Park.
What cuisines can you find in Sherwood?
In Sherwood, travelers can find Thai cuisine, featuring popular dishes like Pad Thai, Green Curry, and Tom Yum soup. There are also options for Latin American fare, including Mexican tacos, as well as Chinese, Japanese, and Italian dishes.
Can I book a refundable hotel in Sherwood?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Sherwood by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Sherwood with Expedia?
Expedia makes it easier to plan your Sherwood trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Sherwood?
The best choice depends on your travel style. Hotels in Sherwood can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Sherwood trip on Expedia?
Once you've booked your Sherwood trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Sherwood trip?
Expedia offers customer support before, during, and after your Sherwood trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Sherwood?
If it's your first trip to Sherwood, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Sherwood hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Sherwood hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Sherwood

Two people in a red canoe on a body of water with a sunset and a bridge in the background.

Tilghman

A waterfront street lined with trees and a white building with a balcony.

Bozman

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