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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Pet friendly

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Pool

Condo

Hot tub

Family friendly

Cottage

Waterpark

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Our top choices for Sherwood hotels

Pet-friendly

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Breakfast included

Hotel

Pool

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

1. Knapps Narrows Marina & Inn

Sherwood

BARBARA

฿4,903

฿5,394 total

includes taxes & fees

30 Aug - 31 Aug

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

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

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.

2. The Tilghman Island Inn

Tilghman

Pamela

฿6,701

฿7,371 total

includes taxes & fees

16 Sept - 17 Sept

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

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

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

฿2,922

฿3,215 total

includes taxes & fees

31 Aug - 1 Sept

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

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

A golf course with a water hazard and surrounding trees.

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

4. Inn at Perry Cabin

Downtown St. Michaels

Andrew

฿14,579

฿16,037 total

includes taxes & fees

7 Sept - 8 Sept

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

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

A modern kitchen with a large island, bar stools, and a wine rack.

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

5. Anchored Inn at Hidden Harbour Marina

Deale

Dale

฿6,512

฿7,424 total

includes taxes & fees

8 Sept - 9 Sept

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

6. Wylder Tilghman Island

Tilghman

Leslie

฿7,252

฿9,611 total

includes taxes & fees

1 Sept - 2 Sept

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

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

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 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.

7. The Wildset

Downtown St. Michaels

Paula

฿7,812

฿9,411 total

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 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.

8. Best Western Plus Easton Inn & Suites

Easton

Margaret

฿4,544

฿4,998 total

includes taxes & fees

30 Aug - 31 Aug

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

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.

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

9. George Brooks House B&B

St. Michaels

Erin

฿6,914

฿7,605 total

includes taxes & fees

31 Aug - 1 Sept

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

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

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.

10. The Oaks Waterfront

Easton

Jeffrey

฿14,386

฿15,825 total

includes taxes & fees

1 Sept - 2 Sept

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

A Holiday Inn Express building with a brick facade, a green roof, and a flagpole with a flag.

An indoor swimming pool with lounge chairs and a no diving sign.

A Holiday Inn Express hotel with a brick facade, a green roof, and a flagpole with the American flag.

11. Holiday Inn Express Easton by IHG

Easton

Alicia

฿5,197

฿5,717 total

includes taxes & fees

30 Aug - 31 Aug

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

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

12. Hampton Inn Easton

Easton

Rachel

฿4,782

฿5,260 total

includes taxes & fees

30 Aug - 31 Aug

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.

13. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

฿5,459

฿6,059 total

includes taxes & fees

8 Sept - 9 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 lobby with a brick wall, three framed pictures, and a patterned carpet.

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

14. Quality Inn

Easton

Erik

฿4,938

฿5,431 total

includes taxes & fees

29 Aug - 30 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.

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

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.

15. Fairfield Inn & Suites by Marriott Easton

Easton

Stephanie

฿4,418

฿4,860 total

includes taxes & fees

6 Sept - 7 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 spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

16. Hilton Garden Inn Kent Island Marina

Grasonville

roney

฿4,798

฿5,326 total

includes taxes & fees

2 Sept - 3 Sept

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

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

17. The Tidewater Inn

Easton

Diana

฿6,178

฿6,796 total

includes taxes & fees

30 Aug - 31 Aug

A grassy area with white Adirondack chairs and a view of sailboats on the water.

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

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.

18. Sandaway Suites & Beach

Oxford

Sandra

฿9,241

฿10,165 total

includes taxes & fees

2 Sept - 3 Sept

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

A spacious lobby with a staircase, a reception desk, and a dining area.

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.

19. Quality Inn Grasonville near Kent Island

Grasonville

Faezeh

฿3,383

฿3,755 total

includes taxes & fees

22 Sept - 23 Sept

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

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.

A hotel reception area with a check-in counter, a digital display, and a red carpet with the hotel's name.

20. Econo Lodge Easton Route 50

Easton

Nicole

฿2,647

฿2,912 total

includes taxes & fees

2 Sept - 3 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 Regency Chesapeake Bay

10/10 Excellent

"Three pools and a hot tub are great. Took advantage of kayak rental on the premises. Our room was clean and the staff were very helpful and friendly."

St Michaels Inn

8/10 Good

"My room was wonderful! Great comfort of the bed. Peaceful. The breakfast was lack luster with all carbs. Nothing sugar free for diabetics. Lots of construction and painting during my stay. Would stay here again, however!"

Sonesta ES Suites Annapolis

10/10 Excellent

"Spacious rooms, very good breakfast selection, even had tacos for breakfast!"

Rod 'N' Reel Resort

10/10 Excellent

"The staff went out of their way for me and I complimented them on how well they took care of the property"

The Westin Annapolis

10/10 Excellent

"Walking distance from the historic main street."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The location of the hotel was awesome along with our balcony view. However you should not have to pay an additional $50 per day to park your car especially since the garage up the street is Therefore the guests are getting pentalized to park at the hotel . Additionally the front desk women were rude and condescending"

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"Very nice hotel in an area of mixed use properties. Convenient to shopping, dining and entertainment"

Graduate by Hilton Annapolis

10/10 Excellent

"I arrived late following a long-distance sailboat race across the Chesapeake Bay. “Nick” was managing the front desk. He was polite, efficient, friendly, and professional. He offered me the best room the hotel had available at my price, and guaranteed I would have a good night’s rest. He was 100% correct. The room was clean and comfortable, and more importantly it was quiet. Check out was easy the next morning."

Crowne Plaza Annapolis by IHG

8/10 Good

"I wish I could give half stars because this place is really a 4.5 stars. First off this place was great, it is everything you need for a hotel. Great prices, friendly staff, very clean, very nice hotel. Why I gave it 4 stars? The coffee machine was down for our first night, the jacuzzi was down for maintenance, the wifi went for maintenance lol so it was a little much but I know you can't always control those things. Another small thing, I also wish the TV's were smart TV's and I wish the rooms came with a microwave. Overall great hotel, would stay here again."

More cheap stays in Sherwood

Best Western Annapolis

2520 Riva Rd Annapolis MD

฿2,480

฿2,827 total

27 Sept - 28 Sept

includes taxes & fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

฿2,922

฿3,215 total

31 Aug - 1 Sept

includes taxes & fees

8/10 Very good! (1,007 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

฿3,200

฿3,648 total

27 Sept - 28 Sept

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

฿3,214

฿3,664 total

27 Sept - 28 Sept

includes taxes & fees

8.4/10 Very good! (1,000 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

฿3,898

฿4,327 total

7 Sept - 8 Sept

includes taxes & fees

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD

฿4,151

฿4,608 total

9 Sept - 10 Sept

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

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.

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Book Hotels in Sherwood on Expedia.com

Find hotels in Sherwood, MD from ฿2,827

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. Inn at Perry Cabin

5. Anchored Inn at Hidden Harbour Marina

6. Wylder Tilghman Island

7. The Wildset

8. Best Western Plus Easton Inn & Suites

9. George Brooks House B&B

10. The Oaks Waterfront

11. Holiday Inn Express Easton by IHG

12. Hampton Inn Easton

13. Hyatt Place Kent Narrows & Marina

14. Quality Inn

15. Fairfield Inn & Suites by Marriott Easton

16. Hilton Garden Inn Kent Island Marina

17. The Tidewater Inn

18. Sandaway Suites & Beach

19. Quality Inn Grasonville near Kent Island

20. Econo Lodge Easton Route 50

Stay near popular Sherwood attractions

Goat Island

Back Creek Community Park

Learn more about Sherwood

Top Sherwood Hotel Reviews

Hyatt Regency Chesapeake Bay

St Michaels Inn

Sonesta ES Suites Annapolis

Rod 'N' Reel Resort

The Westin Annapolis

Annapolis Waterfront Hotel, Autograph Collection

Holiday Inn Express Annapolis East-Kent Island by IHG

Graduate by Hilton Annapolis

Crowne Plaza Annapolis by IHG

More cheap stays in Sherwood

Best Western Annapolis

St Michaels Inn

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Best Western Kent Narrows Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

Frequently asked questions

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