Hotels in Sherwood

Unveil the Secrets of Sherwood: Where Nature Meets Serenity on Idyllic Islands

Nestled on Maryland's picturesque Eastern Shore, Sherwood offers a serene escape for nature lovers and water enthusiasts alike. With its private beach and stunning waterfront views along the Chesapeake Bay, visitors can indulge in leisurely days of sunbathing, fishing, or exploring nearby Tilghman Island. The charming Lowes Wharf Marina serves as a gateway to the region's vibrant marine life and scenic landscapes. Whether you're seeking a romantic getaway or a tranquil retreat, Sherwood's idyllic setting and laid-back atmosphere make it a perfect off-the-beaten-path destination to unwind and reconnect with nature. For the best hotel rates in Sherwood, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Top locations to stay in Sherwood

Some of the best places to stay in Sherwood are Historic District, Eastport and Cape Saint Claire. Sherwood, Maryland offers charming destinations for travelers. The Historic District boasts rich history and quaint boutiques, making it ideal for first-time visitors. Eastport features vibrant waterfront dining and accommodations, including beach inns and hotels with amenities like free parking. Cape Saint Claire provides a relaxed atmosphere with cozy guesthouses. Overall, options like Lowes Wharf Marina Inn offer a unique experience with nearby dining, while hotels in Sherwood cater to various budgets, ensuring a pleasant stay for everyone. Here are some of the most popular hotels with our guests in Sherwood:

1. Historic DistrictOpens in a new window: The Historic District is a vibrant area perfect for families and those looking to dive into culture and history. With attractions like the U.S. Naval Academy and Navy-Marine Corps Memorial Stadium, there's something for everyone. For accommodations, consider Annapolis Waterfront Hotel, Autograph CollectionOpens in a new window, a 4.0-star hotel suited for adventure seekers and business travelers. It offers great amenities including a business center and onsite adventure sports. Another option is The Annapolis InnOpens in a new window, a charming bed and breakfast featuring complimentary full breakfast and a local restaurant guide, ideal for a cozy stay. Lastly, Graduate by Hilton AnnapolisOpens in a new window is pet-friendly and perfect for business travelers, with multiple meeting rooms and a welcoming environment.
2. EastportOpens in a new window: Known for its outdoor activities and close proximity to the waterfront, Eastport captures the essence of Maryland's coastal charm. Visitors can enjoy the nearby U.S. Naval Academy and Westfield Annapolis Mall. The Oaks WaterfrontOpens in a new window is a pet-friendly bed and breakfast that caters to travelers with restrictions on pets. For a luxury experience, Inn at 202 DoverOpens in a new window provides upscale accommodations and business amenities, while Inn at Perry CabinOpens in a new window offers family-friendly options with golf facilities and various business services, making it a great choice for both leisure and work.
3. Cape Saint ClaireOpens in a new window: This picturesque area is perfect for outdoor enthusiasts, boasting attractions like Sandy Point State Park and the Chesapeake Bay Bridge. For your stay, The Inn at Chesapeake Bay Beach ClubOpens in a new window is a great option with business facilities and a full-service spa. If you're an avid golfer, Kent Island ResortOpens in a new window offers specialized amenities for golf lovers, making it an excellent choice for a peaceful retreat. Additionally, Inn at Huntingfield CreekOpens in a new window provides spa services and a relaxing environment, ensuring a rejuvenating experience amid the scenic beauty of Cape Saint Claire.

Things to do in Sherwood for first time

Spend three idyllic days in Sherwood, where stunning beaches meet lush forests. Enjoy sailing on serene waters, explore hiking trails, and unwind with breathtaking sunsets. Experience the thrill of kayaking and discover the beauty of the surrounding islands, making it a perfect retreat for nature lovers and adventure seekers alike. Here's a quick itinerary to make the most of your trip to Sherwood:

• Day 1: Begin your adventure at the Chesapeake Bay Maritime Museum, where you can explore fascinating exhibits about the region's maritime history and culture. After immersing yourself in the local heritage, head over to the Phillips Wharf Environmental Center. Here, you can engage with interactive displays and enjoy the beautiful waterfront views. Conclude your day with a visit to the Tilghman Watermen’s Museum, where you can learn about the life and traditions of the watermen who work the Chesapeake Bay.
• Day 2: Start your day with an exhilarating Rod n Reel Charter Fishing experience, where you can cast a line and hopefully reel in a big catch. After a morning on the water, take a scenic drive to Upper Yough River, perfect for a leisurely afternoon of canoeing or kayaking. Wrap up your day at Breezy Point Beach, where you can relax on the sandy shore, enjoy a picnic, and watch the sunset over the bay.
• Day 3: Kick off with a stunning view at the Chesapeake Bay Bridge, a marvel of engineering that offers breathtaking vistas. Afterward, explore the Chesapeake Bay Environmental Center, where you can learn about the local ecosystems and enjoy walking along the trails. End your itinerary at Sandy Point State Park, where you can unwind with a hike, take a dip in the bay, or simply relax on the beach as you reflect on your adventures in this beautiful region.

5 tips to find a great Sherwood hotel deal

1. Book for the cheapest times: The most affordable time to visit Sherwood is during January, February, and December, when hotel prices are at their lowest. For a budget-friendly experience, plan to stay for at least 2-3 days to fully enjoy the area’s main attractions, including its stunning nature and picturesque marina. This timeframe offers great value for money, allowing you to immerse yourself in the beauty of the region while keeping costs down.
2. Look for last-minute deals on Hotels.com: If you're seeking affordable options for your stay in Sherwood, last-minute deals can be a great way to score cheap room rates. To explore these opportunities on Hotels.com, simply head to the DealsOpens in a new window or Last-Minute DealsOpens in a new window section, where you could find enticing discounts as your travel date approaches. Additionally, sign up for email alerts or push notifications from Hotels.com to stay informed about flash sales and special promotions, helping you maximize your savings while planning your trip.
3. Be flexible with dates: Hotel prices can fluctuate depending on factors like the hotel's location, star rating, and the time of year. As a result, if you remain flexible with your travel dates, you may save on hotel expenses in Sherwood.
4. Consider your location: When booking on Hotels.com for your holiday, think about your location. Staying near key attractions or city centers can be convenient, but it usually tends to come with a higher price tag. For more affordable options, consider hotels in less central areas or neighborhoods, finding a balance between cost and easy access to the places you want to visit.
5. Upgrade with One Key: Make your next booking in Sherwood and sign up to Hotels.com's free One Key program, letting you earn and use reward points on your next stay. Progress through the Blue, Silver, Gold and Platinum tiers to unlock various advantages like room upgrades when available, discounted rates, and exclusive offers for members. Don't hesitate, sign up today.

Best time to go to Sherwood

Sherwood experiences its lowest average temperature in January, at 36.3°F (2.4°C), while July is the hottest month, with an average temperature of 78.4°F (25.8°C). August is usually the wettest month. March to May are the peak travel months in Sherwood, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, with light rainfall. On the other hand, January, February, and November tend to be quieter times to visit, marked by light rainfall and mostly sunny conditions.