Find hotels in Sherwood, MD from ¥12,668

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Compare 1,155 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
9.2 out of 10, Wonderful, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is ¥12,271
¥13,620 total
includes taxes & fees
Dec 18 - Dec 19
Holiday Inn Express Annapolis East-Kent Island by IHG

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1003)
"Room was great! In room tub was a bit smaller than I was expecting but still quite adequate! View from room was very nice."
United States
Madeline
The price is ¥16,030
¥17,793 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Kent Island Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.6 out of 10, Exceptional, (673)
"Great view, good ambiance all around"
United States
Dianne
The price is ¥18,034
¥20,018 total
includes taxes & fees
Dec 14 - Dec 15
Hyatt Place Kent Narrows & Marina

DoubleTree by Hilton Hotel Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1007)
"Great place!"
United States
Tawnya
The price is ¥12,864
¥14,665 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Hotel Annapolis

The Westin Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1001)
"Great environment"
United States
Salvador E
The price is ¥23,921
¥27,271 total
includes taxes & fees
Dec 14 - Dec 15
The Westin Annapolis

Hampton Inn & Suites Annapolis

2.5 star property
Annapolis
8.2 out of 10, Very Good, (1001)
"I had a great experience at my stay at Hampton "
United States
Idris O
The price is ¥13,421
¥15,300 total
includes taxes & fees
Dec 17 - Dec 18
Hampton Inn & Suites Annapolis

Crowne Plaza Annapolis by IHG

3.5 star property
Annapolis
8.8 out of 10, Excellent, (1003)
"Clean, easy parking, nice staff but over priced breakfast"
United States
Gabrielle
The price is ¥15,067
¥17,176 total
includes taxes & fees
Dec 15 - Dec 16
Crowne Plaza Annapolis by IHG

Holiday Inn Express Prince Frederick by IHG

2.5 star property
Prince Frederick
8.8 out of 10, Excellent, (690)
"Loved it"
United States
Francisco
The price is ¥15,999
¥19,483 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express Prince Frederick by IHG

Courtyard by Marriott Annapolis

3.0 star property
Annapolis
8.6 out of 10, Excellent, (1001)
"Wonderful stay. "
United States
Angela
The price is ¥15,067
¥17,177 total
includes taxes & fees
Dec 28 - Dec 29
Courtyard by Marriott Annapolis

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (880)
"Great location, nice and clean "
United States
Micah
The price is ¥27,594
¥31,458 total
includes taxes & fees
Dec 14 - Dec 15
Annapolis Waterfront Hotel, Autograph Collection

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is ¥19,814
¥27,447 total
includes taxes & fees
Dec 11 - Dec 12
Kent Island Resort

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1901)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
Annapolis
8.2 out of 10, Very Good, (1000)
"Clean room and friendly staff! "
United States
Silvia
The price is ¥12,426
¥14,166 total
includes taxes & fees
Dec 20 - Dec 21
Holiday Inn Express & Suites Annapolis by IHG

Hilton Garden Inn Annapolis

3.0 star property
Annapolis
8.2 out of 10, Very Good, (1003)
"I had a lovely stay."
United States
Kalynn
The price is ¥11,557
¥13,174 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis Downtown

3.0 star property
Annapolis
8.6 out of 10, Excellent, (1001)
"Great value for stay with breakfast included "
United States
Aisling
The price is ¥12,302
¥14,025 total
includes taxes & fees
Dec 28 - Dec 29
Hilton Garden Inn Annapolis Downtown

SureStay by Best Western Prince Frederick

2.5 star property
Prince Frederick
7.6 out of 10, Good, (204)
"The room was great and very clean, good location and overall great and affordable we did enjoy it, thank you."
United States
Evelio
The price is ¥11,412
¥12,668 total
includes taxes & fees
Dec 9 - Dec 10
SureStay by Best Western Prince Frederick

Hyatt Regency Chesapeake Bay

4.0 star property
Cambridge
8.8 out of 10, Excellent, (1001)
"Very courteous staff."
United States
Joseph
The price is ¥27,594
¥35,513 total
includes taxes & fees
Dec 15 - Dec 16
Hyatt Regency Chesapeake Bay

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is ¥16,517
¥21,441 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Rod 'N' Reel Resort

Sonesta ES Suites Annapolis

3.0 star property
Edgewater
8.8 out of 10, Excellent, (960)
"Nice breakfast, clean room, great parking"
United States
Amy
The price is ¥14,135
¥16,114 total
includes taxes & fees
Dec 28 - Dec 29
Sonesta ES Suites Annapolis

SpringHill Suites by Marriott Annapolis

3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1000)
"Friendly staff and comfortable rooms. We love staying here when we visit the area as a family."
United States
Jennifer
The price is ¥15,712
¥17,911 total
includes taxes & fees
Dec 14 - Dec 15
SpringHill Suites by Marriott 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

Find out more about Sherwood

Top reasons to visit Sherwood

  • Outdoor Activities: Enjoy scenic recreational areas perfect for picnics and outdoor fun with family and friends.
  • Cultural Experiences: Explore fascinating history museums and vibrant local culture, including Avenida Guatemala.
  • Beautiful Parks: Relax in urban parks that offer picturesque views and romantic strolls.
  • Family-Friendly Atmosphere: Discover nearby attractions that cater to both children and adults.
  • Charming Accommodations: Choose from cozy bed and breakfasts or comfortable hotels with essential amenities.

Find great hotels near Sherwood

Discover an array of charming accommodations in Sherwood, Maryland, perfect for your vacation needs. Whether you prefer a cozy bed and breakfast or a comfortable hotel, you'll find options that cater to pet-friendly travelers and those seeking adventure. Look for essential amenities such as air conditioning, adjoining rooms, and delicious buffet breakfasts to enhance your stay while enjoying the area's beautiful beach vacation experience.

  • St Michaels Inn: Experience the perfect blend of adventure and business at St Michaels Inn, located 9.7km from Sherwood. This hotel is ideal for travelers seeking an active vacation with a professional edge. The property boasts business-friendly amenities including a Conference Space, Conference Center, and Meeting Rooms, making it suitable for corporate gatherings. For those looking to explore the outdoors, guests can enjoy nearby adventure sports such as hiking, biking, hunting, and fishing. With its focus on both work and play, St Michaels Inn is a great choice for dynamic travelers.
  • Rod 'N' Reel Resort: Situated 20.9km from Sherwood, Rod 'N' Reel Resort is a welcoming 3-star hotel perfect for family vacations and LGBTQIA travelers. This resort combines business amenities, such as multiple Meeting Rooms and Conference Spaces, with family-friendly features, including a Ping Pong Table and Arcade Game Room for children to enjoy. With its inclusive atmosphere and recreational activities, this resort is ideal for families looking to create lasting memories while attending to business needs.
  • The Tidewater Inn: The Tidewater Inn, located 20.9km from Sherwood, offers a unique blend of business, adventure, and relaxation. This charming 3-star hotel provides a full-service spa, complete with couples' treatment rooms and various body and facial treatments, ensuring guests unwind after a day of exploration. It also caters to business travelers with a comprehensive Business Center and Meeting Rooms. Guests can partake in nearby adventures such as sailing, kayaking, and biking, making it a versatile choice for those seeking both relaxation and excitement.

Where to stay near Sherwood

Experience the charm of Sherwood, Maryland, where outdoor adventures and cultural exploration await you. Discover the scenic beauty of local parks, enjoy romantic strolls through friendly neighborhoods, and soak in the sunny weather. Nearby attractions offer a family-friendly atmosphere, with historical sites and vibrant city views. Don’t miss Avenida Guatemala for a taste of local flavor and culture, making your vacation both relaxing and enriching.

  • St. Michaels: Located a mere 8.0km from Sherwood, St. Michaels is a charming town that thrives on its natural beauty and outdoor activities. Visitors are drawn here for its romantic ambiance, family-friendly experiences, and picturesque boardwalks. The area boasts lovely beaches and serene lakes, making it ideal for leisurely strolls or engaging in recreational activities. With peak tourist seasons in April and from June to July, St. Michaels offers a vibrant atmosphere for those looking to enjoy the great outdoors.
  • Tilghman: Just 6.4km from Sherwood, Tilghman is a tranquil haven perfect for outdoor enthusiasts and those seeking scenic views. The town experiences a seasonal influx of travelers, particularly from June to August, as people flock to its stunning beaches and lakes. The recreational areas and boardwalk provide ample opportunities for relaxation and exploration. Tilghman's romantic charm and breathtaking scenery make it a must-visit destination for anyone looking to connect with nature.
  • Bozman: A short 4.8km from Sherwood, Bozman offers a unique blend of outdoor adventure and serene landscapes. This city sees steady visitor traffic year-round, with peaks in March and from June to July. Travelers are attracted to its beautiful beaches and family-friendly lakes, which serve as perfect spots for relaxation and fun. Bozman's outdoor recreational areas and boardwalks invite you to immerse yourself in nature while enjoying romantic sunsets and scenic vistas.

Things to do near Sherwood

Sherwood, Maryland, offers a charming blend of outdoor activities, romantic settings, and cultural experiences. Visitors can enjoy the scenic recreational areas, educational opportunities, and a delightful boardwalk. For a perfect day out, don’t miss the picnic areas, perfect for relaxing with family and friends amidst nature. Whether you're exploring or simply unwinding, Sherwood provides an inviting atmosphere for a memorable vacation.

Shopping

In Sherwood, you can visit Saint Michaels Village, a charming shopping center just 9.7km away, perfect for gifts and souvenirs. If you're up for a drive, Easton Cycle and Sport is located 22.5km away, while the Bay Bridge Market Place Shopping Center is 19.7km away and offers a vibrant shopping experience.

Recreation

Enjoy a round of golf at Hog Neck Golf Course, where you can embrace the outdoor vibes and stunning landscapes just 24.1km from Sherwood. For relaxation, Talbot Massage offers rejuvenating body treatments 22.5km away, while the Ballet Theater of Maryland, located 29.0km away, provides a charming cultural experience with captivating performances.

Adventure

Chesapeake Beach Water Park, located 20.9km from Sherwood, offers thrilling water slides and family-friendly attractions for a splash-tastic day. St. Michaels Nature Trail, 8.0km away, invites you to explore scenic paths amidst nature. For sailing enthusiasts, Annapolis Sailing School, 25.7km distant, provides exciting water sports adventures.

Nightlife

Experience the charm of Avalon Theatre, 20.9km from Sherwood, offering a blend of culture and romance. For some fun, visit Annapolis Bowl, 32.2km away, where adventure awaits in an arcade atmosphere. Don't miss Regal Waugh Chapel, 43.5km from Sherwood, for a perfect movie night with a romantic vibe.

*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 during your visit to Sherwood, plan your trip between January and March for lower hotel rates, avoiding the pricier June and fall months. Tuesdays are the cheapest days to stay, while Saturdays are the most expensive. Utilize Expedia’s search tool to find budget-friendly accommodations, and consider booking package deals that combine flights, hotels, and activities for added savings. Don't forget to look for genius discounts and check cancellation policies to ensure you're getting the best value for your trip.

  • 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: Expedia's search tool makes it easy for you to set your budget, choose your desired location, and much more. You can arrange your search results to display prices from lowest to highest, helping you find the most affordable hotels right away. Additionally, you can narrow down your options by hotel type; for instance, if you select the Eco-certified filter, you'll see a list of sustainable and eco-friendly hotels that you can book.
  • Consider bundling your trip: You can save money by combining your Sherwood hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Sherwood

Sherwood, Maryland, offers a delightful blend of outdoor activities and cultural experiences, making it ideal for a romantic getaway or a family adventure. Visitors can explore fascinating history museums, enjoy scenic views at the marina, and relax in urban parks, ensuring a diverse range of attractions to discover. Whether you're seeking outdoor fun or an enriching cultural experience, Sherwood has something for everyone.

  • Chesapeake Bay Maritime Museum: Located 9.7km from Sherwood, this museum offers a deep dive into the rich maritime history of the Chesapeake Bay. Explore engaging exhibits, historic boats, and the vibrant culture of the region, all set against the stunning backdrop of the bay.
  • Tilghman Watermen’s Museum: Just 6.4km away, this museum celebrates the life and heritage of watermen on Tilghman Island. Discover fascinating exhibits that highlight the local fishing industry and the unique stories of those who depend on the bay for their livelihood.
  • Tilghman Island Marina: Located 4.8km from Sherwood, this marina is perfect for outdoor enthusiasts. Enjoy boating, fishing, and water sports, all while soaking up the sun and beach vibes along the beautiful shoreline.

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

When visiting Sherwood, Maryland, you have several airport options. Washington, DC (DCA-Ronald Reagan Washington National) is 62.8km away, with nearby luxury hotels like the InterContinental Washington D.C. - The Wharf and Riggs Washington DC, both offering convenient access to the airport. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is 54.7km away, featuring the Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, which provide airport shuttle services. Lastly, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) is 83.7km away, with options like Country Inn & Suites and Courtyard by Marriott, both easily accessible from the airport.

Frequently asked questions

Where is the best place to stay in Sherwood?
Crowne Plaza Annapolis by IHG, located 19.7 mi (31.7 km) from the heart of Sherwood, is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are Historic Inns of Annapolis and DoubleTree by Hilton Hotel Annapolis. See all available top hotels, or vacation rentals in Sherwood.
What's the top vacation rental that Sherwood has to offer?
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28: You might want to consider this vacation home rental near Sherwood, which is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Sherwood.
If I need to cancel my hotel reservation in Sherwood, will I receive a refund?
Yes, most room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, you might still have the option to cancel and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sherwood.
Where can I learn more about changing or cancelling my trip to Sherwood?
To find more details about changing or cancelling your trip to Sherwood, head over to our customer service page.
What's the best pet-friendly place to stay in Sherwood?
Lowes Wharf Marina Inn is a top inn for people traveling with their pets, and offers a marina and a restaurant for its human guests. See more pet-friendly hotel accommodations in Sherwood.
What are some hotels with pools in Sherwood?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Sonesta ES Suites Annapolis and Hyatt Regency Chesapeake Bay are a couple of other choices that feature an onsite pool. View all hotels with pools in Sherwood.
What's the best hotel for staying near Salisbury - Ocean City Wicomico Regional Airport (SBY)?
Country Inn & Suites by Radisson, Salisbury, MD is one of the top choices for your stay and is a popular 3-star hotel featuring free breakfast and an indoor pool. It's located 2.2 mi (3.6 km) from Salisbury - Ocean City Wicomico Regional Airport. Other options close to the airport include Microtel Inn & Suites by Wyndham Salisbury and Sleep Inn Salisbury.
What's it like to stay in Sherwood?
Visitors can enjoy all that Sherwood has to offer including the waterfront and restaurants. This city also attracts tourists with its scenic and welcoming setting. In Sherwood, there are 8 hotels and other accommodations to choose from. Find out more about Sherwood.
What should I do while I'm visiting Sherwood?
A couple of favorite places to visit are Knapp's Narrows Marina & Inn and Goat Island. You'll also find St. Michaels Winery and St. Michaels Marina in the area. Check out what more to see and do in Expedia's Sherwood guide.
What's the weather like in Sherwood?
The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 41°F. Average annual precipitation for Sherwood is 53 inches.

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