𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Sherwood (2026)

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

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Our top choices for Sherwood hotels

Breakfast included

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Motel

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

A building with a sign reading "The Inn."

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

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

1. Knapps Narrows Marina & Inn

Sherwood

BARBARA

S$209

includes taxes & fees

25 Aug - 26 Aug

An outdoor bar area with a view of the lake, wooden deck, and metal roof structure.

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

A modern lounge area with a fireplace, seating, and a view of the outdoors.

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

2. The Tilghman Island Inn

Tilghman

Pamela

S$286

includes taxes & fees

25 Aug - 26 Aug

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

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

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.

3. St Michaels Inn

St. Michaels

Karen

S$117

includes taxes & fees

31 Aug - 1 Sept

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

A waterfront hotel with a covered dock and a large building with multiple balconies.

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

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

4. Wylder Tilghman Island

Tilghman

Leslie

S$371

includes taxes & fees

3 Sept - 4 Sept

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

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

5. The Wildset

Downtown St. Michaels

Paula

S$365

includes taxes & fees

8 Sept - 9 Sept

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

6. Best Western Plus Easton Inn & Suites

Easton

Margaret

S$194

includes taxes & fees

25 Aug - 26 Aug

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

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

A restaurant with a high ceiling, large windows, and a central bar area.

A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.

7. Rod 'N' Reel Resort

Chesapeake Beach

Tessa

S$181

includes taxes & fees

3 Sept - 4 Sept

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

A four-poster bed with a floral bedspread, a large bathtub, and a chair in a room with green walls and wooden floors.

A dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.

A two-story house with a wrap-around porch, multiple chimneys, and a well-maintained front yard.

8. George Brooks House B&B

St. Michaels

Erin

S$295

includes taxes & fees

31 Aug - 1 Sept

A modern building with large windows, a brick facade, and a well-maintained lawn with flower beds.

A hotel reception area with a wooden counter, a large sailboat painting, and a waffle station.

A swimming pool with lounge chairs and a covered area, surrounded by a fence and buildings.

A lobby with a brick wall, three framed pictures, and a patterned carpet.

9. Quality Inn

Easton

Karen

S$145

includes taxes & fees

27 Aug - 28 Aug

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

A golf course with a water hazard and surrounding trees.

10. Inn at Perry Cabin

Downtown St. Michaels

Andrew

S$594

includes taxes & fees

7 Sept - 8 Sept

A buffet with labeled food stations including omelets and cheese.

A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.

An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty.

A lobby with two green armchairs, a small round table, a flat-screen TV mounted on the wall, and a patterned rug on the floor.

11. Holiday Inn Express Easton by IHG

Easton

Alicia

S$222

includes taxes & fees

25 Aug - 26 Aug

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".

A bedroom with a large bed, a nightstand, a lamp, and a window with blinds.

A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.

12. The Tidewater Inn

Easton

Diana

S$227

includes taxes & fees

26 Aug - 27 Aug

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

13. Fairfield Inn & Suites by Marriott Easton

Easton

Stephanie

S$189

includes taxes & fees

30 Aug - 31 Aug

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.

A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

14. Quality Inn Grasonville near Kent Island

Grasonville

Faezeh

S$142

includes taxes & fees

14 Sept - 15 Sept

A patio with outdoor seating, overlooking a marina with boats.

A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

An indoor swimming pool with clear views of boats and water.

A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

15. Hilton Garden Inn Kent Island Marina

Grasonville

roney

S$207

includes taxes & fees

31 Aug - 1 Sept

A modern hotel dining area with a long table, four chairs, and three pendant lights.

A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.

A hotel hallway with carpeted floors, white doors, and overhead lighting.

16. Hampton Inn Easton

Easton

Jason

S$222

includes taxes & fees

23 Sept - 24 Sept

A hotel room with two beds, a desk, a TV, and a window with curtains.

A building with a sign reading "EcoLodge."

A covered corridor with a series of doors, each marked with a number.

A breakfast bar with a waffle maker, coffee machine, and juice dispenser.

17. Econo Lodge Easton Route 50

Easton

michael

S$113

includes taxes & fees

31 Aug - 1 Sept

A swimming pool with a mural, lounge chairs, and a hot tub.

A patio area with lounge chairs, a table, and umbrellas.

A multi-story hotel with a central courtyard, a flag, and a sign indicating it is a Radisson hotel.

A hotel room with a large bed, a separate sitting area, a bathtub, and a view of the outdoors.

18. Best Western Kent Narrows Inn

Grasonville

chanel

S$179

includes taxes & fees

31 Aug - 1 Sept

A large, two-story barn-style building with a covered front porch and a garage.

A large, two-story white house with a porch and multiple windows.

A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

19. Kent Island Resort

Stevensville

Leigh

S$260

includes taxes & fees

10 Sept - 11 Sept

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 modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

20. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

S$235

includes taxes & fees

8 Sept - 9 Sept

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Stay near popular Sherwood attractions

Goat Island

Commune with nature and explore the great outdoors at Goat Island during your travels in Sherwood. Wander the marina or discover the area's sunsets.

See properties

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.

See properties

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.

See all hotels in Sherwood

Top Sherwood Hotel Reviews

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"our ocean facing room was beautiful. We enjoyed staying here."

Sonesta ES Suites Annapolis

10/10 Excellent

"I thought the room and facilities were great. It was annoying that a guest was playing basketball at 8AM outside my window. But everything else was great. The staff were very nice!"

Rod 'N' Reel Resort

10/10 Excellent

"."

Crowne Plaza Annapolis by IHG

8/10 Good

"Generally, the facility is fine - two things regarding room: 1) no grab bar in side shower 2) no bar soap in bathroom."

St Michaels Inn

8/10 Good

"It seems the hotel is under going renovation. Parts of it were nice and updated, others were very rundown looking. The staff were all very friendly and helpful. Our room was fine, bed was comfortable, it looked newly updated which was nice. The breakfast was typical hotel continental. It's a good place stay for the money."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"Balcony was great so was the view, hotel getting a little old needs some room cosmetics, location great"

Courtyard by Marriott Annapolis

10/10 Excellent

"Clean room and staff was very courteous."

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"Perfect for what I needed"

Hyatt Regency Chesapeake Bay

10/10 Excellent

"Excellent well-maintained rooms with new ceiling fan. Summer amenities are geared to families and include mini golf, multiple pools indoors & outdoors, day spa, convenience shop with coffee , pool tables (although not as well maintained as other areas of the property), walking paths, and a regulationgolf course. Families can be quite boisterous; we will opt for calmer winter months in future."

More cheap stays in Sherwood

Best Western Annapolis

2520 Riva Rd Annapolis MD

S$116

30 Aug - 31 Aug

includes taxes & fees

7.8/10 Good! (1,010 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

S$117

31 Aug - 1 Sept

includes taxes & fees

8/10 Very good! (1,018 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

S$141

30 Aug - 31 Aug

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

S$152

30 Aug - 31 Aug

includes taxes & fees

8.4/10 Very good! (1,010 reviews)

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD

S$179

1 Sept - 2 Sept

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

S$179

31 Aug - 1 Sept

includes taxes & fees

Frequently asked questions

Where is the best place to stay in Sherwood?

Knapps Narrows Marina & Inn is one of the top choices for your stay based on our traveller data. This hotel is a short 14-minute walk from Chesapeake Bay, and it offers a marina and free breakfast. Two other choices for your stay in the area are DoubleTree by Hilton Hotel Annapolis and Historic Inns of Annapolis. See all available top hotels, or vacation rentals in Sherwood.

If I need to cancel my hotel reservation in Sherwood, will I receive a refund?

Yes, most hotel reservations are fully refundable as long as you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Sherwood.

What's the best dog-friendly place to stay in Sherwood?

Lowes Wharf Marina Inn is a top inn for people travelling 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?

Knapps Narrows Marina & Inn: Hotel, 14-minute walk from Chesapeake Bay. Features daily, a seasonal outdoor pool and free self parking. Crowne Plaza Annapolis by IHG and Rod 'N' Reel Resort are a couple of other choices with an on-site pool. View all hotels with pools in Sherwood.

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 accommodation options to choose from. Find out more about Sherwood.

What are the top places to visit in Sherwood?

A couple of favourite 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. Take a look at what more there is to see and do in Expedia's Sherwood guide.

What's the seasonal weather like in Sherwood?

The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Sherwood is 1341 mm.

Sherwood Hotels from S$113

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Sherwood

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Sherwood hotels

1. Knapps Narrows Marina & Inn

2. The Tilghman Island Inn

3. St Michaels Inn

4. Wylder Tilghman Island

5. The Wildset

6. Best Western Plus Easton Inn & Suites

7. Rod 'N' Reel Resort

8. George Brooks House B&B

9. Quality Inn

10. Inn at Perry Cabin

11. Holiday Inn Express Easton by IHG

12. The Tidewater Inn

13. Fairfield Inn & Suites by Marriott Easton

14. Quality Inn Grasonville near Kent Island

15. Hilton Garden Inn Kent Island Marina

16. Hampton Inn Easton

17. Econo Lodge Easton Route 50

18. Best Western Kent Narrows Inn

19. Kent Island Resort

20. Hyatt Place Kent Narrows & Marina

Stay near popular Sherwood attractions

Goat Island

Back Creek Community Park

Learn more about Sherwood

Top Sherwood Hotel Reviews

Hyatt Place Kent Narrows & Marina

Sonesta ES Suites Annapolis

Rod 'N' Reel Resort

Crowne Plaza Annapolis by IHG

St Michaels Inn

Annapolis Waterfront Hotel, Autograph Collection

Courtyard by Marriott Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Hyatt Regency Chesapeake Bay

More cheap stays in Sherwood

Best Western Annapolis

St Michaels Inn

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

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