Top 10 Hotels in Sherwood, MD (from $84) 2026 - Competitive Prices

A large brick house with a green roof, surrounded by lush gardens and trees.

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Our top choices for Sherwood hotels

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

A marina with multiple boats docked during sunset.

An aerial view of a coastal town with a marina, houses, and a bridge in the background.

A historic brick building with a red roof, multiple windows, and a central staircase.

1. Historic Inns of Annapolis

Historic District

Robert

$122 nightly

$139 total

Nov 12 - Nov 13

Total with taxes and fees

An outdoor seating area with tables and chairs, overlooking a body of water and greenery.

A waterfront property with a dock, a sailboat, and a building with a red roof.

A spacious indoor dining area with large windows, tables, and chairs.

A large building with a swimming pool, dock, and green surroundings.

2. The Tilghman Island Inn

Tilghman

William

$185 nightly

$204 total

Oct 19 - Oct 20

Total with taxes and fees

A marina with boats docked at wooden piers, surrounded by greenery.

A waterfront property with houses, a dock, and a grassy area.

A bed with two pillows, one with "HAPPY PLACE" text, and a framed picture above the bed.

A covered patio area with wicker furniture and a view of a building with large windows.

3. Knapps Narrows Marina & Inn

Sherwood

Bonnie

$150 nightly

$165 total

Oct 19 - Oct 20

Total with taxes and fees

An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.

A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.

A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.

A marina with boats docked, a sandy beach, and a clear blue sky.

4. Hyatt Regency Chesapeake Bay

Cambridge

Carolyn

$171 nightly

$194 total

Nov 18 - Nov 19

Total with taxes and fees

A waterfront property with a covered patio, a dock, and a boat.

A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.

A view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.

5. Wylder Tilghman Island

Tilghman

Angela

$241 nightly

$265 total

Oct 20 - Oct 21

Total with taxes and fees

A two-story building with a covered entrance and an American flag.

A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

6. St Michaels Inn

St. Michaels

Mary

$81 nightly

$89 total

Nov 17 - Nov 18

Total with taxes and fees

A room with a view of a wooden deck and a gazebo by the water.

A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

A golf course with a water hazard and surrounding trees.

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

7. Inn at Perry Cabin

Downtown St. Michaels

Christina

$491 nightly

$540 total

Nov 18 - Nov 19

Total with taxes and fees

A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

A modern bar area with a long counter and multiple bar stools.

A bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.

A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

8. Rod 'N' Reel Resort

Chesapeake Beach

Pam

$132 nightly

$146 total

Nov 5 - Nov 6

Total with taxes and fees

A balcony with a table set for two, overlooking a marina with boats.

A waterfront area with boats docked, a clear sky, and buildings in the background.

A hotel room with a large bed, a chair, a small table, and a view of a body of water.

A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

9. Annapolis Waterfront Hotel, Autograph Collection

Historic District

Nila

$223 nightly

$254 total

Nov 2 - Nov 3

Total with taxes and fees

A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

A spacious atrium with a high ceiling, skylights, and a patterned floor.

A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.

10. Graduate by Hilton Annapolis

Annapolis

Nadine

$147 nightly

$167 total

Oct 26 - Oct 27

Total with taxes and fees

A two-story house with a porch, a front door, and a small garden area.

A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.

A dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.

A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

11. The Wildset

Downtown St. Michaels

Bonnie

$252 nightly

$277 total

Nov 3 - Nov 4

Total with taxes and fees

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.

A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.

A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

12. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

$105 nightly

$120 total

Nov 16 - Nov 17

Total with taxes and fees

A bar area with multiple seating options, including bar stools and tables, and a variety of bottles and glasses on shelves.

A hotel lobby with a long bar area, seating, and a projection screen.

A Comfort Inn hotel with a parking lot and a covered entrance.

An outdoor seating area with tables and chairs, blue umbrellas, and a brick building in the background.

13. Comfort Inn Conference Center

Bowie

Gary

$109 nightly

$123 total

Oct 25 - Oct 26

Total with taxes and fees

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

14. DoubleTree by Hilton Hotel Annapolis

Annapolis

PATRICK

$114 nightly

$130 total

Oct 25 - Oct 26

Total with taxes and fees

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

An outdoor event area with round tables and a view of the water.

A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

15. Hyatt Place Kent Narrows & Marina

Grasonville

Susan

$152 nightly

$169 total

Oct 25 - Oct 26

Total with taxes and fees

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

A wooden console table with framed floral artwork, two lamps, and two ottomans.

A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.

16. The Oaks Waterfront

Easton

Matthew

$489 nightly

$538 total

Oct 19 - Oct 20

Total with taxes and fees

A conference room with a long table, chairs, and a carpeted floor.

17. Hilton Garden Inn Annapolis Downtown

Annapolis

Andrea

$104 nightly

$119 total

Nov 1 - Nov 2

Total with taxes and fees

A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.

A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

18. Courtyard by Marriott Annapolis

Annapolis

joe

$100 nightly

$114 total

Nov 9 - Nov 10

Total with taxes and fees

A lakeside view with sailboats, grassy areas, and white Adirondack chairs.

A bottle of Merlot wine and two glasses on a wooden tray by a window overlooking a lake.

A beach with clear water, sandy shore, and some vegetation.

A large, two-story house with a balcony, situated on a grassy lawn with autumn leaves, near a body of water.

19. Sandaway Suites & Beach

Oxford

Kathleen

$290 nightly

$319 total

Nov 18 - Nov 19

Total with taxes and fees

A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

A modern lobby with a reception desk, seating area, and a patterned rug.

A gym with treadmills, weight machines, and dumbbells.

A patio area with a stone fire pit, outdoor furniture, and a covered seating area.

20. Sonesta ES Suites Annapolis

Edgewater

Dennis

$92 nightly

$105 total

Nov 16 - Nov 17

Total with taxes and fees

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Where to stay near Sherwood

Sherwood offers a delightful escape with its beautiful outdoor scenery and friendly atmosphere. Explore nearby areas for adventure and romance, all while enjoying family-friendly activities and relaxing days under sunny skies. It's the perfect destination for those seeking a charming and scenic getaway.

A lighthouse on stilts with a green roof, surrounded by water and greenery.

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

A golf course with bunkers, a large body of water, and a bridge in the distance.

A lighthouse at sunset with a boat docked nearby.

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

St. Michaels

Discover St. Michaels, a charming destination perfectly suited for families and couples seeking outdoor adventures and picturesque scenery. This delightful city offers a range of experiences, from the engaging exhibits at the Chesapeake Bay Maritime Museum to the iconic 1879 Hooper Strait Lighthouse and scenic strolls along the St. Michaels Marina. Located about 12 miles by car from Sherwood, St. Michaels makes for a smart hotel booking choice, ensuring a memorable getaway amidst nature's beauty.

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Bozman

Experience the charm of Bozman, an excellent hub for travelers seeking a weekend getaway with family or a nature-focused retreat. Just about 6 miles by car from Sherwood, Bozman offers easy access to scenic spots like the Chesapeake Bay Maritime Museum and the historic 1879 Hooper Straight Lighthouse, alongside opportunities for outdoor recreation at St. Michaels Marina. With its blend of beach and lake experiences, Bozman is a smart choice for your next vacation stay.

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Wittman

If you are a nature enthusiast or a family traveler, look no further than Wittman, a charming city known for its scenic beauty and outdoor adventures. Visitors can explore the Chesapeake Bay Maritime Museum, marvel at the historic 1879 Hooper Straight Lighthouse, or relax at St. Michaels Marina. Wittman is about a 3-mile drive from Sherwood, making it easy to access the area's stunning bay and beach. Choosing Wittman for your stay ensures a delightful blend of relaxation and exploration.

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An aerial view of a coastal town with a long peninsula extending into the sea, surrounded by water and greenery.

A marina with boats docked and a sunset in the background.

A rocky shoreline with waves crashing onto the beach, a clear blue sky, and a forested area in the distance.

Tilghman

Ideally situated for families, nature lovers, and couples seeking a romantic getaway, Tilghman is a charming destination that invites visitors to immerse themselves in its stunning scenery. Just a short drive from Sherwood, Tilghman offers easy access to outdoor recreational areas, a beautiful bay, and a welcoming beach. Explore local highlights like the Tilghman Island Marina, the Tilghman Watermen’s Museum, and the Phillips Wharf Environmental Center. Choosing Tilghman for your stay ensures a memorable experience in a picturesque setting.

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Neavitt

Travelers seeking a weekend getaway will find Neavitt to be the ideal base for their vacation, featuring stunning outdoor experiences and family-friendly activities. With attractions like the Chesapeake Bay Maritime Museum, the Tilghman Island Marina, and the picturesque 1879 Hooper Straight Lighthouse, visitors can immerse themselves in the natural beauty and rich maritime heritage of the area. Located about 17 miles by car from Sherwood, Neavitt offers a delightful escape that makes it a smart choice for your stay.

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Stay near popular attractions in and around Sherwood

Experience the perfect blend of outdoor adventures and cultural richness in Sherwood. With stunning parks, a picturesque marina, and engaging museums, you'll find endless activities that cater to families and nature lovers alike. Discover the beauty and charm that makes Sherwood an unforgettable getaway.

Chesapeake Bay Maritime Museum

9.4/10 (91 reviews)

Set the stage for your exploration of Maryland's rich maritime heritage at the Chesapeake Bay Maritime Museum. This engaging museum showcases the area's unique culture through exhibits and activities that highlight the region's boating history. It's about a 13-mile drive from Sherwood, making it a convenient stop for your vacation itinerary.

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A large suspension bridge over a calm body of water with a sunset in the background.

Northern Chesapeake Bay

Perfectly suited for nature lovers and beachgoers, Northern Chesapeake Bay offers stunning outdoor scenery and vibrant beach vibes. Located about 13 miles from Sherwood, this picturesque bay invites visitors to explore its natural beauty and enjoy a relaxing escape, making it a convenient getaway for your vacation.

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Phillips Wharf Environmental Center

10.0/10 (3 reviews)

Often cited as a favorite among nature lovers, Phillips Wharf Environmental Center offers a unique opportunity to explore local wildlife and engage with eco-friendly initiatives. Located about 3 miles by car from Sherwood, this center makes for an easy visit, perfect for those looking to connect with nature while enjoying the area's charm.

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Tilghman Watermen’s Museum

9.8/10 (6 reviews)

The perfect blend of culture and history, Tilghman Watermen’s Museum is ideal for travelers interested in exploring the rich maritime heritage of the Chesapeake Bay. Located about 5 miles by car from Sherwood, this museum offers a unique glimpse into the lives of local watermen, making it a convenient stop during your visit.

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St. Michaels Museum

8.6/10 (9 reviews)

No trip is complete without a visit to St. Michaels Museum, a charming history museum that immerses visitors in the rich cultural heritage of the area. Located about 13 miles by car from Sherwood, this spot offers a unique glimpse into local history, making it an easy and rewarding addition to your itinerary.

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Oxford Museum

8.2/10 (25 reviews)

An essential stop for history buffs, Oxford Museum offers a unique glimpse into the rich cultural heritage of the region. Located about 23 miles by car from Sherwood, this museum immerses visitors in fascinating exhibits. Staying nearby makes it easy to explore this vibrant historical site.

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Rod n Reel Charter Fishing

7.6/10 (31 reviews)

A perfect spot for fishing enthusiasts, Rod n Reel Charter Fishing offers a unique blend of outdoor adventure and maritime charm. Located about 13 miles from Sherwood, this marina invites visitors to enjoy a day on the water, making it a convenient choice for a memorable fishing experience.

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Shadyside Park

A must-see for families, Shadyside Park offers a delightful blend of outdoor activities and vibrant city vibes. Just about 12 miles from Sherwood, this urban park features ample green space for picnics and play, making it an ideal spot for a refreshing escape. Staying nearby ensures easy access to this community gem.

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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.

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Top Sherwood Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"Clean room, very nice decor and great staff"

St Michaels Inn

8/10 Good

"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Perfect place to stay! Classy. Clean comfortable amazing staff"

Knapps Narrows Marina & Inn

10/10 Excellent

"The staff was extremely helpful and the view was amazing. I will definitely be returning."

Best Western Annapolis

8/10 Good

"Noisy balcony"

Baymont by Wyndham Easton

10/10 Excellent

"Staff who received us was very helpful and respectful. Breakfast was great, rooms are well maintained and clean."

More cheap stays in Sherwood

Best Western Annapolis

2520 Riva Rd Annapolis MD

$76 nightly

$86 total

Nov 1 - Nov 2

Total with taxes and fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

$81 nightly

$89 total

Nov 17 - Nov 18

Total with taxes and fees

8/10 Very Good! (1,001 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

$90 nightly

$100 total

Nov 8 - Nov 9

Total with taxes and fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

$95 nightly

$108 total

Nov 16 - Nov 17

Total with taxes and fees

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

$98 nightly

$111 total

Nov 1 - Nov 2

Total with taxes and fees

Best Western Plus Easton Inn & Suites

8708 Alicia Drive Easton MD

$119 nightly

$131 total

Nov 15 - Nov 16

Total with taxes and fees

Hotels in Sherwood with star-rating

Find out more about Sherwood

Top reasons to visit Sherwood

Scenic Outdoor Activities: Sherwood offers beautiful outdoor spaces, perfect for relaxation and exploration, including a private beach and access to the Chesapeake Bay.
Vibrant Local Scene: Enjoy live music events that contribute to the lively atmosphere of the community.
Rich Cultural Experiences: Visit nearby history museums and urban parks for a taste of local culture.
Family-Friendly Vibe: Sherwood is ideal for families seeking a peaceful and enjoyable getaway.
Comfortable Accommodations: Choose from charming bed & breakfasts to modern hotels, catering to all needs.

Find great hotels near Sherwood

Discover a range of comfortable accommodations in Sherwood, Maryland, perfect for your vacation. Whether you're seeking a cozy bed & breakfast or a modern hotel, you'll find options that cater to your needs. Enjoy pet-friendly facilities and amenities like free Wi-Fi at popular spots such as the Lowes Wharf Marina Inn and Residence Inn. Experience the adventure and beach vibes that make Sherwood a great destination for travelers.

St Michaels Inn: St Michaels Inn is a budget-friendly hotel with a guest rating of 8.2 out of 10, located 6 miles from Sherwood. This property caters to adventurers and business travelers alike, providing a range of outdoor activities nearby. Guests can enjoy bicycle rentals, hiking, hunting, and fishing in the surrounding areas. The Inn offers a cozy atmosphere perfect for those seeking an affordable yet adventurous stay, making it a great choice for those looking to explore the natural beauty of the region.
Rod 'N' Reel Resort: With a guest rating of 8.4 out of 10, Rod 'N' Reel Resort is a 3-star establishment situated 13 miles from Sherwood. Ideal for families and adventure seekers, this resort features a variety of onsite activities, including boat tours, fishing, and personal motor watercraft rentals. For families, amenities such as a ping pong table, arcade game room, and special breakfast options for children enhance the experience. The resort’s blend of fun and relaxation makes it a perfect destination for both leisure and business travelers.
The Tidewater Inn: Rated 8.8 out of 10, The Tidewater Inn is a charming 3-star hotel located 13 miles from Sherwood. This property offers a unique combination of adventure and relaxation with activities like kayaking, sailing, and hiking nearby. For those seeking rejuvenation, the full-service spa provides couples' treatment rooms, massages, and body scrubs. The Tidewater Inn is an excellent choice for travelers looking to unwind in a serene environment while enjoying a variety of recreational options.

Where to stay near Sherwood

Explore the charming town of Sherwood, Maryland, where outdoor adventures and scenic views await. Enjoy the tranquil atmosphere at the private beach and wharf, or take a trip to the nearby Chesapeake Bay for a delightful island experience. With its friendly locals and family-friendly vibe, Sherwood is the perfect destination for those seeking relaxation and historical charm. Discover the beauty of this sunny region during your vacation.

St. Michaels: Nestled approximately 5 miles from Sherwood, St. Michaels is a charming coastal town renowned for its picturesque scenery and outdoor activities. The town experiences a moderate influx of visitors, particularly during April and the summer months of June and July. Travelers flock here to enjoy the beautiful beaches, scenic views, and vibrant boardwalks. St. Michaels boasts a variety of recreational areas where you can relax and soak up the sun, making it ideal for both family outings and romantic getaways. Local attractions include the family-friendly beach and the stunning bay, which are perfect for water sports or leisurely strolls.
Bozman: Located just 3 miles from Sherwood, Bozman is a hidden gem that offers a unique blend of outdoor adventures and scenic beauty. This city sees a steady stream of visitors throughout the year, peaking in March and the summer months of June to July. Here, you can explore the inviting recreational areas and enjoy a day of shopping at local centers. The nearby bay and lake provide ample opportunities for fishing, kayaking, or simply enjoying a day by the water. Bozman's welcoming atmosphere and natural beauty make it a perfect spot for those seeking a quieter, more laid-back experience.
Wittman: Also situated 3 miles from Sherwood, Wittman is an inviting town that attracts visitors year-round, especially in the summer months from June to August. Known for its stunning outdoor spaces and serene scenery, Wittman is perfect for nature enthusiasts. The area offers various recreational opportunities, including boardwalks and parks, where you can immerse yourself in the area's natural beauty. Nearby attractions include the beautiful bay, beach, and national state park, making Wittman a great base for exploring the great outdoors while enjoying the local charm.

Things to do near Sherwood

In Sherwood, Maryland, visitors can enjoy a delightful blend of outdoor activities and scenic beauty. The area features a recreational space perfect for relaxation, a charming boardwalk, and educational opportunities. Don't miss out on the vibrant local scene, highlighted by live music events that add to the community's lively atmosphere. Whether you're looking for a beach getaway or just a peaceful retreat, Sherwood has something for everyone.

Shopping

In Sherwood, you can explore local shops for unique gifts and souvenirs. If you're up for a drive, head to nearby shopping malls like the Montgomery Mall or the Westfield Wheaton for a wider selection of stores and dining options to enhance your shopping experience.

Recreation

At Old South Country Club, just 19 miles from Sherwood, immerse yourself in luxury with top-notch wellness amenities. Enjoy serene golf courses, rejuvenating spa treatments, and upscale dining options, all set against a picturesque backdrop, perfect for relaxation and rejuvenation.

Adventure

In Sherwood, explore the scenic trails of Patuxent River Park for hiking and biking adventures. Experience thrilling water activities on the Patuxent River, including kayaking and canoeing, perfect for nature lovers seeking excitement and relaxation amidst stunning views.

Nightlife

Explore the vibrant nightlife at the Sherwood Lounge, where you can enjoy signature cocktails and a lively atmosphere. For dancing, check out the nearby Club 47, featuring local DJs and themed nights that keep the energy high and the party going.

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

Booking tips and Expedia advantages for Sherwood

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 narrow down your options based on your preferences, such as budget, desired location, and hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
Consider bundling your trip: You can save money by combining your hotel stay in Sherwood with your flights and activities through an Expedia package deal.

Find the best attractions near Sherwood

Sherwood, Maryland, is perfect for outdoor enthusiasts and families seeking a scenic beach vacation. You can explore a variety of attractions, including marinas, urban parks, and history museums, which offer rich cultural experiences. Whether you're looking to enjoy nature or delve into local history, Sherwood has something for everyone, ensuring a memorable getaway.

Chesapeake Bay Maritime Museum: Located 6 miles from Sherwood, this maritime museum offers a deep dive into the rich cultural heritage of the Chesapeake Bay. Explore exhibits showcasing traditional boat building, local wildlife, and the maritime history of the region.
Rod n Reel Charter Fishing: A short 13 miles away, this marina is perfect for those seeking adventure on the water. Enjoy charter fishing trips that provide thrilling experiences against the beautiful backdrop of the bay, along with opportunities for outdoor fun on the beach.
Tilghman Watermen’s Museum: Just 4 miles from Sherwood, this history museum highlights the lives and traditions of local watermen. Engage with exhibits that celebrate the unique culture and history of the fishing community in the area.

Best time to go to Sherwood

The best time to visit Sherwood is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	36.3°F (2.4°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	38.8°F (3.8°C)	Light Rain	Mostly Sunny	Low	Slightly Low
March	45.3°F (7.4°C)	Light Rain	Mostly Sunny	High	Slightly Low
April	55.6°F (13.1°C)	Light Rain	Mostly Sunny	High	Average
May	64.6°F (18.1°C)	Light Rain	Mostly Sunny	High	Average
June	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	78.4°F (25.8°C)	Light Rain	Mostly Sunny	Average	Average
August	76.8°F (24.9°C)	Light Rain	Mostly Sunny	Average	Average
September	71.1°F (21.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	61.0°F (16.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	49.5°F (9.7°C)	Light Rain	Mostly Sunny	Average	Average
December	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Average

The nearest major airports for your trip to Sherwood

When planning your trip to Sherwood, Maryland, you'll find convenient access to three major airports. Ronald Reagan Washington National Airport (DCA) is 39 miles away, with excellent nearby hotels like the 5-star InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both just 2 miles from the airport. Washington Dulles International Airport (IAD) is 62 miles distant, featuring hotels such as the 4-star Westin Washington Dulles Airport and Hyatt Regency Dulles International Airport, both 1 mile away. Lastly, Baltimore Washington International Airport (BWI) is 34 miles from Sherwood, offering luxurious options like Pendry Baltimore and Four Seasons Hotel Baltimore, approximately 8 miles from the airport.

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 much is the nightly rate at a Sherwood hotel?

Prices for hotels in Sherwood often vary, but you can find a great deal from $84 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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Our top choices for Sherwood hotels

1. Historic Inns of Annapolis

2. The Tilghman Island Inn

3. Knapps Narrows Marina & Inn

4. Hyatt Regency Chesapeake Bay

5. Wylder Tilghman Island

6. St Michaels Inn

7. Inn at Perry Cabin

8. Rod 'N' Reel Resort

9. Annapolis Waterfront Hotel, Autograph Collection

10. Graduate by Hilton Annapolis

11. The Wildset

12. Crowne Plaza Annapolis by IHG

13. Comfort Inn Conference Center

14. DoubleTree by Hilton Hotel Annapolis

15. Hyatt Place Kent Narrows & Marina

16. The Oaks Waterfront

17. Hilton Garden Inn Annapolis Downtown

18. Courtyard by Marriott Annapolis

19. Sandaway Suites & Beach

20. Sonesta ES Suites Annapolis

Where to stay near Sherwood

St. Michaels

Bozman

Wittman

Tilghman

Neavitt

Stay near popular attractions in and around Sherwood

Chesapeake Bay Maritime Museum

Northern Chesapeake Bay

Phillips Wharf Environmental Center

Tilghman Watermen’s Museum

St. Michaels Museum

Oxford Museum

Rod n Reel Charter Fishing

Shadyside Park

Learn more about Sherwood

Top Sherwood Hotel Reviews

Graduate by Hilton Annapolis

St Michaels Inn

The Inn at Chesapeake Bay Beach Club

Annapolis Waterfront Hotel, Autograph Collection

Knapps Narrows Marina & Inn

Best Western Annapolis

Baymont by Wyndham Easton

More cheap stays in Sherwood

Best Western Annapolis

St Michaels Inn

Best Western Kent Narrows Inn

Holiday Inn Express & Suites Annapolis by IHG

Hampton Inn & Suites Annapolis

Best Western Plus Easton Inn & Suites

Hotels in Sherwood with star-rating

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