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Our top choices for Sherwood hotels

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121 reviews)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
$160 nightly
The price is $176
Feb 15 - Feb 16
Total with taxes and fees
The Tilghman Island Inn

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (374 reviews)
"Beautiful place to stay."
United States
Ellen
$513 nightly
The price is $564
Feb 18 - Feb 19
Total with taxes and fees
Inn at Perry Cabin

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (368 reviews)
"Always a great time. "
United States
Randolph
$90 nightly
The price is $99
Feb 13 - Feb 14
Total with taxes and fees
Knapps Narrows Marina & Inn

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (92 reviews)
"We were"
United States
Guevara
$167 nightly
The price is $184
Mar 1 - Mar 2
Total with taxes and fees
Wylder Tilghman Island

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,005 reviews)
"Great service, great food and drinks. "
United States
Kelly
$211 nightly
The price is $240
Feb 22 - Feb 23
Total with taxes and fees
Hyatt Regency Chesapeake Bay

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,000 reviews)
"Good value and close to downtown."
United States
John
$88 nightly
The price is $97
Feb 17 - Feb 18
Total with taxes and fees
St Michaels Inn

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (417 reviews)
"Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown. "
United States
Fred
$199 nightly
The price is $219
Feb 16 - Feb 17
Total with taxes and fees
The Wildset

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
" Beautiful property, wonderful staff, excellent food service."
United States
Seth
$459 nightly
The price is $505
Feb 13 - Feb 14
Total with taxes and fees
The Oaks Waterfront

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (901 reviews)
"Great location, nice and clean "
United States
Micah
$203 nightly
The price is $232
Feb 22 - Feb 23
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,875 reviews)
"Great rooms, very clean, loved our stay "
United States
Matthew
$229 nightly
The price is $261
Feb 26 - Feb 27
Total with taxes and fees
Historic Inns of Annapolis

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (131 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
$149 nightly
The price is $164
Feb 16 - Feb 17
Total with taxes and fees
Parsonage Inn

Sandaway Suites & Beach

Sandaway Suites & Beach
3.0 star property
Oxford
9.4 out of 10, Exceptional, (156 reviews)
"VERY pleasant stay at Sandaway! "
United States
Gilbert
Sandaway Suites & Beach

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1,001 reviews)
"Yes the room was clean and the staff was great "
United States
Thurnell
$128 nightly
The price is $140
Feb 24 - Feb 25
Total with taxes and fees
Rod 'N' Reel Resort

Black Walnut Point Inn

Black Walnut Point Inn
3.5 star property
Tilghman
9.0 out of 10, Wonderful, (56 reviews)
"Wife and I stayed 3 days for 41st anniversary. Bob and Tracy are wonderful hosts. "
United States
Ernest
Black Walnut Point Inn

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (67 reviews)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
$170 nightly
The price is $187
Feb 16 - Feb 17
Total with taxes and fees
George Brooks House B&B

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,007 reviews)
"Room was clean, great location"
United States
Brian
$164 nightly
The price is $187
Feb 22 - Feb 23
Total with taxes and fees
Graduate by Hilton Annapolis

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,002 reviews)
"Quiet lodging, great location "
United States
Daniel
$99 nightly
The price is $112
Feb 16 - Feb 17
Total with taxes and fees
Comfort Inn Conference Center

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,001 reviews)
"Great stay "
United States
Jose Miguel
$83 nightly
The price is $94
Feb 22 - Feb 23
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (712 reviews)
"Amazing location and staff!"
United States
Bobbi J.
$116 nightly
The price is $129
Mar 2 - Mar 3
Total with taxes and fees
Hyatt Place Kent Narrows & Marina

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,001 reviews)
"Great hotel love that they are pet friendly. Easy check in and valet parking staff great"
United States
Robert
$169 nightly
The price is $193
Feb 15 - Feb 16
Total with taxes and fees
The Westin Annapolis
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.

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Stay near popular Sherwood attractions

Learn more about Sherwood

Explore the historic Sherwood Forest community with its charming waterfront homes and private marina along the Severn River. Nearby Annapolis offers sailing excursions, while local residents enjoy exclusive access to the community beach and tennis courts.

Gardens and large home at Sherwood Gardens Park, in Baltimore, M

Top Sherwood Hotel Reviews

More cheap stays in Sherwood

Hotels in Sherwood with star-rating

Find out more about Sherwood

Top reasons to visit Sherwood

  • Scenic Outdoor Recreation: Enjoy picturesque views and outdoor adventures in Sherwood's recreational areas and urban parks.
  • Charming Local Culture: Immerse yourself in the local culture, featuring history museums and vibrant community events.
  • Beautiful Sunsets: Witness stunning sunsets that provide a breathtaking backdrop along the eastern shore.
  • Welcoming Accommodations: Choose from a variety of charming bed and breakfasts and pet-friendly hotels.
  • Live Music Events: Relax with live music while enjoying outdoor seating and a lively atmosphere.

Find great hotels near Sherwood

In Sherwood, Maryland, you’ll discover a variety of lodging options, including charming bed and breakfasts and convenient hotels. Ideal for travelers seeking pet-friendly accommodations and adventure-filled beach experiences, the area offers essential amenities such as free Wi-Fi, meeting rooms, and positive hotel reviews. Whether you’re planning a relaxing getaway or a lively vacation, Sherwood has the perfect place for you to unwind and enjoy your stay.

  • St Michaels Inn: Nestled 6 miles from Sherwood, St Michaels Inn caters to travelers seeking a blend of business efficiency and adventure. This hotel is equipped with essential business amenities, including a Conference Center and Meeting Rooms, making it perfect for corporate guests. For those craving outdoor excitement, the property offers nearby opportunities for hunting, hiking, biking, and fishing, ensuring that every guest finds an exhilarating experience. The combination of professional facilities and adventure activities makes St Michaels Inn an excellent choice for the active business traveler.
  • Rod 'N' Reel Resort: Located 13 miles from Sherwood, Rod 'N' Reel Resort is a family-friendly escape that warmly welcomes LGBTQIA travelers. This 3-star hotel is perfect for adventure seekers and families alike, featuring onsite kayaking, fishing, and personal motor watercraft rentals. Kids can enjoy the fun-filled arcade game room and ping pong table, making it an ideal destination for families. With its inclusive atmosphere and plethora of outdoor activities, Rod 'N' Reel Resort promises a memorable vacation for everyone.
  • The Tidewater Inn: Positioned 13 miles from Sherwood, The Tidewater Inn is a charming blend of business and relaxation. This 3-star hotel offers multiple meeting rooms and a business center, catering to corporate guests. For relaxation, indulge in their full-service spa featuring reflexology and hot stone massages. Adventure enthusiasts can explore nearby sailing, kayaking, and hiking opportunities. The Tidewater Inn provides the perfect combination of business facilities and rejuvenating amenities, making it a standout choice for travelers seeking both productivity and leisure.

Where to stay near Sherwood

Discover the charming allure of Sherwood, Maryland, where outdoor adventures and romantic getaways await. Explore the picturesque eastern shore, enjoy local hangouts with friendly faces, and soak in breathtaking river views. Don't miss the chance to witness fantastic sunsets that paint the sky in vibrant hues. With a family-friendly atmosphere and rich history nearby, Sherwood is the perfect destination for a relaxing vacation filled with diverse cultural experiences.

  • St. Michaels: Located 5 miles from Sherwood, St. Michaels is a charming town that attracts visitors with its picturesque waterfront and vibrant community. Known for its outdoor and family-friendly activities, the area features scenic boardwalks and recreational spots perfect for leisurely strolls or family outings. The peak travel months in April and June to July bring a lively atmosphere, as tourists flock to enjoy the local beaches and lakes. Whether you're looking for a romantic getaway or a fun-filled family adventure, St. Michaels offers a variety of attractions that will make your visit memorable.
  • Tilghman: Just 4 miles from Sherwood, Tilghman is a serene destination renowned for its breathtaking scenery and tranquil beaches. The city draws visitors primarily during the summer months of June to August, making it an ideal spot for outdoor enthusiasts and couples seeking a romantic escape. Enjoy the scenic beauty while exploring recreational areas and boardwalks that line the water's edge. With its proximity to family-friendly beaches and serene lakes, Tilghman promises a relaxing getaway amidst nature's charm.
  • Bozman: Located 3 miles from Sherwood, Bozman is a hidden gem that offers a peaceful retreat throughout the year. Although visitor numbers peak in March and June to July, this city remains inviting for those seeking outdoor activities and scenic views. Bozman is perfect for romantic outings and family adventures, with access to beautiful beaches, lakes, and recreational areas. The boardwalks provide an excellent opportunity for leisurely walks, making Bozman a delightful destination for any traveler looking to unwind and explore.

Things to do near Sherwood

Experience the charm of Sherwood, Maryland, perfect for outdoor and romantic getaways. Enjoy the scenic recreational areas, stroll along the boardwalk, and immerse yourself in local culture. Don't miss live music events while relaxing in outdoor seating with beach chairs, making for a delightful vacation. Sherwood offers a blend of relaxation and entertainment, ensuring a memorable visit for all tourists.

Shopping

In Sherwood, you can find unique gifts at Easton Cycle and Sport, located 14 miles away. If you're up for a drive, check out the Bay Bridge Market Place Shopping Center and Paul Reed Smith Guitars, both 16 miles away, offering a mix of entertainment and specialty items.

Recreation

Hog Neck Golf Course offers a scenic golfing experience surrounded by nature, perfect for sports enthusiasts. Talbot Massage provides rejuvenating body treatments in a tranquil setting, ensuring complete relaxation. For a cultural touch, the Ballet Theater of Maryland showcases captivating performances, blending art and entertainment beautifully.

Adventure

At Chesapeake Beach Water Park, located 13 miles from Sherwood, enjoy thrilling water slides and family-friendly activities in a vibrant atmosphere. Experience outdoor excitement at Annapolis Sailing School, 16 miles away, offering sailing adventures on beautiful waters. Hike the scenic B&A Trail, 27 miles from Sherwood, for stunning views and outdoor exploration.

Nightlife

Experience the vibrant nightlife by catching a show at Avalon Theatre, just 13 miles away, or enjoy family fun at Annapolis Bowl, located 20 miles from Sherwood. For more culture and romance, The Colonial Players, 18 miles away, offers captivating performances.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Sherwood

To save money on your trip to Sherwood, Maryland, consider visiting during the off-peak months of January to March, when prices are lower. Tuesdays are the cheapest days to book accommodations, while Saturdays tend to be the most expensive. Use Expedia to filter hotel options by budget and eco-certification, and consider package deals to combine flights and hotels for additional savings. Don't forget to join Expedia's One Key membership for exclusive discounts and rewards on future bookings, helping you make the most of your travel budget.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Sherwood are January to March, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Sherwood is Tuesday. The most expensive day to stay in Sherwood is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your options based on your budget, preferred destination, and the type of hotel you want. For instance, selecting the Eco-certified filter will show you sustainable and eco-friendly hotels that are currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Sherwood hotel reservation with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Sherwood

Sherwood, Maryland, offers a delightful blend of outdoor adventures and cultural experiences perfect for a romantic getaway or family vacation. Visitors can explore local attractions such as the history museum, unwind at the marina, or enjoy leisurely strolls in the urban park. With its diverse points of interest, Sherwood caters to travelers seeking both relaxation and enriching experiences in a charming setting.

  • Chesapeake Bay Maritime Museum: Located 6 miles from Sherwood, this maritime museum offers a deep dive into the rich maritime heritage of the Chesapeake Bay. Explore interactive exhibits, historic vessels, and enjoy picturesque views of the waterfront, immersing yourself in the region's culture.
  • Tilghman Watermen’s Museum: Just 4 miles away, this history museum showcases the life of watermen on Tilghman Island. Through engaging displays and local artifacts, you’ll gain insight into the traditions and challenges of the fishing community, all while appreciating the cultural vibes.
  • Phillips Wharf Environmental Center: Situated 3 miles from Sherwood, this eco-friendly center focuses on conservation and education. Experience hands-on activities, learn about local ecosystems, and see the importance of protecting the environment in a business-friendly atmosphere.

Best time to go to Sherwood

The best time to visit Sherwood can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Sherwood falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Sherwood falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.3°F (2.4°C)Light RainMostly SunnyAverageSlightly Low
February38.8°F (3.8°C)Light RainMostly SunnyLowSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyHighSlightly Low
April55.6°F (13.1°C)Light RainMostly SunnyHighAverage
May64.6°F (18.1°C)Light RainMostly SunnyHighAverage
June73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
July78.4°F (25.8°C)Light RainMostly SunnyAverageAverage
August76.8°F (24.9°C)Light RainMostly SunnyAverageAverage
September71.1°F (21.7°C)Light RainMostly SunnyAverageSlightly High
October61.0°F (16.1°C)Light RainMostly SunnyAverageSlightly High
November49.5°F (9.7°C)Light RainMostly SunnyAverageAverage
December42.3°F (5.7°C)Light RainMostly SunnyAverageAverage

The nearest major airports for your trip to Sherwood

Traveling to Sherwood, Maryland, is convenient with access to three major airports. Washington, DC (DCA-Ronald Reagan Washington National) is 39 miles away, with nearby hotels like InterContinental Washington D.C. - The Wharf and Riggs Washington DC, both offering easy transportation options. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is 34 miles from Sherwood, featuring luxurious stays such as Sagamore Pendry Baltimore, which provides various shuttle services. Lastly, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) is 52 miles away, with options like Country Inn & Suites by Radisson just 2 miles from the airport, ensuring smooth access for travelers.

Frequently asked questions

What is the best area to stay in Sherwood?
The best area to stay in Sherwood, Maryland, is along the waterfront, particularly around the Sherwood Road and Claiborne Road intersection, where many of the town's key amenities are located.

This central area offers direct access to the Chesapeake Bay, providing scenic water views and opportunities for activities like kayaking or paddleboarding. It's the hub for local dining and community gatherings, making it convenient for visitors to experience the local character.

Couples often find this area appealing due to the serene waterfront setting and the availability of accommodations with Bay views. The proximity to local eateries and the public pier creates a relaxing environment for romantic strolls and enjoying sunsets over the water.

For travelers seeking a quiet retreat with easy access to nature, the areas slightly inland from the main waterfront, particularly near the fishing and crabbing spots, offer a peaceful escape.
When is the best time to go to Sherwood?
The best time to visit Sherwood, Maryland, is during the shoulder seasons of late spring (April-May) and early fall (September-October).

During these months, you'll experience pleasant temperatures, fewer crowds, and a full range of outdoor activities. The weather is typically sunny and mild, superb for exploring the Chesapeake Bay, enjoying watersports, or hiking the local trails without the intense heat and humidity of summer. Many local establishments, from eateries to attractions, are fully operational, offering a complete experience for visitors.

For those looking for a quiet, relaxing getaway, these times of year are ideal. You can enjoy the natural beauty of the area, like the scenic views along the Chesapeake Bay, and take advantage of outdoor activities like kayaking or biking without the peak season influx of people.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Sherwood.
How can I save on a Sherwood hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Sherwood hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Sherwood hotel?
Prices for hotels in Sherwood often vary, but you can find a great deal from $90 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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