Sherwood Holiday Rentals, Maryland: Private House Rentals

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

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

A building with a sign reading "The Inn."

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

1. Knapps Narrows Marina & Inn

Sherwood

BARBARA

฿5,030

฿5,532 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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.

2. The Tilghman Island Inn

Tilghman

William

฿6,203

฿6,823 total

includes taxes & fees

12 Oct - 13 Oct

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

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.

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

3. Wylder Tilghman Island

Tilghman

Gary

฿8,148

฿10,639 total

includes taxes & fees

18 Oct - 19 Oct

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

A two-story building with a balcony on the upper floor, outdoor seating with wooden chairs and tables, and a clear view of the surrounding area.

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.

4. The Wildset

Downtown St. Michaels

Sarah

฿7,678

฿9,284 total

includes taxes & fees

3 Nov - 4 Nov

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

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

A golf course with a water hazard and surrounding trees.

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

5. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

฿17,201

฿18,921 total

includes taxes & fees

8 Nov - 9 Nov

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

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.

A hotel room with two beds, a chair, and a painting on the wall.

6. St Michaels Inn

St. Michaels

Lynn

฿2,867

฿3,153 total

includes taxes & fees

1 Nov - 2 Nov

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

A white colonial-style house with a covered porch, brick steps, and outdoor seating.

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

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

7. The Oaks Waterfront

Easton

Jeffrey

฿14,757

฿16,232 total

includes taxes & fees

12 Oct - 13 Oct

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

A living room with a fireplace, a sofa, a chair, and a bookshelf.

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

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

฿6,488

฿7,137 total

includes taxes & fees

2 Nov - 3 Nov

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

A four-poster bed with a floral bedspread, a nightstand with a lamp, and a chair with a cushion.

An outdoor patio with a round wooden table and chairs, surrounded by potted plants and a brick wall.

A cozy room with a fireplace, a framed picture above it, and two armchairs.

9. Parsonage Inn

Downtown St. Michaels

Paul

฿8,383

฿9,221 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.

10. Best Western Plus Easton Inn & Suites

Easton

Lori

฿4,325

฿4,758 total

includes taxes & fees

12 Oct - 13 Oct

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

A reception area with two reception desks, a wall-mounted sign reading "Holiday Inn Express," and a telephone on the right side.

A coffee station with two coffee machines and a variety of coffee pods and cups.

11. Holiday Inn Express Easton by IHG

Easton

Emily

฿4,996

฿5,496 total

includes taxes & fees

18 Oct - 19 Oct

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.

A hotel with a covered entrance, multiple floors, and a parking lot.

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

12. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

฿4,532

฿4,985 total

includes taxes & fees

18 Oct - 19 Oct

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

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

13. Rod 'N' Reel Resort

Chesapeake Beach

Kathleen K

฿4,848

฿5,381 total

includes taxes & fees

20 Oct - 21 Oct

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

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

A waterfront bar with outdoor seating, a view of the water, and American flags.

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

14. Sandaway Suites & Beach

Oxford

Amber

฿10,058

฿11,064 total

includes taxes & fees

22 Oct - 23 Oct

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

A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

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.

15. Hampton Inn Easton

Easton

Rachel

฿4,288

฿4,717 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

16. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

฿5,097

฿5,657 total

includes taxes & fees

18 Oct - 19 Oct

A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.

A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.

A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

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

17. Baymont by Wyndham Easton

Easton

Ellen

฿2,988

฿3,286 total

includes taxes & fees

12 Oct - 13 Oct

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

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

A spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.

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

18. The Tidewater Inn

Easton

Miriam

฿6,002

฿6,602 total

includes taxes & fees

1 Nov - 2 Nov

A multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.

A marina with docked boats, a picnic area, and a grassy lawn with a tree.

A marina with boats docked at wooden piers, surrounded by greenery and houses in the background.

A modern kitchen with a bar area, wooden flooring, and blue bar stools.

19. Anchored Inn at Hidden Harbour Marina

Deale

Beverly

฿6,219

฿7,090 total

includes taxes & fees

12 Oct - 13 Oct

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

20. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

฿6,840

฿8,446 total

includes taxes & fees

2 Nov - 3 Nov

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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

Rod 'N' Reel Resort

10/10 Excellent

"Overall a great place to stay, very clean, and updated, price was more then expected, breakfast should of been included. Also a lot of hidden fees. Overall enjoyed our stay. Free parking was a plus. I am thinking about returning for my 60th birthday."

Hampton Inn & Suites Annapolis

8/10 Good

"Everything was great here except the plug for the tub didnt work."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Had an amazing stay here. The room was spotlessly clean from top to bottom. The linens were fresh, the bathroom was pristine, and everything felt completely sanitized. It’s rare to find a property that pays such close attention to detail. Fantastic housekeeping service!"

St Michaels Inn

10/10 Excellent

"We travel to St micheals md, several times a year, during the oyster season. Usually we stay at hotels in easton, so this time we tried the st micheals inn. It's closer to the Cheasapeake Landing restaurant. We were placed in a room opposite the main street, which made for a very quiet evening. Much better than those hotels off rt.50. The breakfast was a "hot" breakfast and included with the stay. The beds are comfortable, and the showers hot and forceful."

The Westin Annapolis

10/10 Excellent

"Easy parking. Super comfy bed."

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"no"

Knapps Narrows Marina & Inn

10/10 Excellent

"I will be back! Beautiful surroundings in a very well maintained, locally staffed (and guessing owned in conjunction with the marina), quaint hotel. The sound of the moored boats out front was soothing and the place was spic and span. Front desk staff are very friendly and great with recommendations."

More cheap stays in Sherwood

Best Western Annapolis

2520 Riva Rd Annapolis MD

฿2,656

฿3,027 total

13 Oct - 14 Oct

includes taxes & fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

฿2,867

฿3,153 total

1 Nov - 2 Nov

includes taxes & fees

8/10 Very good! (1,004 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

฿3,014

฿3,345 total

8 Nov - 9 Nov

includes taxes & fees

8/10 Very good! (1,004 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

฿3,185

฿3,631 total

9 Nov - 10 Nov

includes taxes & fees

8.4/10 Very good! (1,001 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

฿3,272

฿3,730 total

18 Oct - 19 Oct

includes taxes & fees

8.2/10 Very good! (1,001 reviews)

Best Western Plus Easton Inn & Suites

8708 Alicia Drive Easton MD

฿4,325

฿4,758 total

12 Oct - 13 Oct

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 Saint Michaels Town Hall 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.

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Find hotels in Sherwood, MD from ฿2,987

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. Wylder Tilghman Island

4. The Wildset

5. Inn at Perry Cabin

6. St Michaels Inn

7. The Oaks Waterfront

8. George Brooks House B&B

9. Parsonage Inn

10. Best Western Plus Easton Inn & Suites

11. Holiday Inn Express Easton by IHG

12. Fairfield Inn & Suites by Marriott Easton

13. Rod 'N' Reel Resort

14. Sandaway Suites & Beach

15. Hampton Inn Easton

16. Hyatt Place Kent Narrows & Marina

17. Baymont by Wyndham Easton

18. The Tidewater Inn

19. Anchored Inn at Hidden Harbour Marina

20. The Inn at Chesapeake Bay Beach Club

Stay near popular Sherwood attractions

Goat Island

Back Creek Community Park

Learn more about Sherwood

Top Sherwood Hotel Reviews

Rod 'N' Reel Resort

Hampton Inn & Suites Annapolis

The Inn at Chesapeake Bay Beach Club

St Michaels Inn

The Westin Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Knapps Narrows Marina & Inn

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

Frequently asked questions

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