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

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Our top choices for Sherwood holiday homes

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

An aerial view of a marina with numerous boats docked, surrounded by residential and commercial buildings.

A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

1. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

9.8 out of 10, Exceptional, (56 reviews)

9.8/10

Exceptional

(56 reviews)

"very clean home, quiet neighborhood in a great location."

Anthony P.

The price is £226

£226

includes taxes & fees

26 Oct - 27 Oct

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

A dining table set with pink bowls and glasses, surrounded by chairs, with a large plant and a window in the background.

A living room with a blue sofa, a round mirror, and a coffee table.

2. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

10.0 out of 10, Exceptional, (24 reviews)

10/10

Exceptional

(24 reviews)

"Cute, family friendly home. Had everything we needed for a comfortable stay."

Johanna S.

The price is £242

£242

includes taxes & fees

23 Oct - 24 Oct

Beachside Oasis with Beach Passes & King Suite by A Haven Away

A lighthouse with a white exterior, a balcony, and a metal roof.

A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

A bedroom with a wooden floor, a bed with a white and yellow bedspread, a nightstand, and a window with a view of the outdoors.

A spacious living room with a sofa set, a coffee table, and a dining area with a table and chairs.

3. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

9.8 out of 10, Exceptional, (47 reviews)

9.8/10

Exceptional

(47 reviews)

"Great stay"

Michael V.

The price is £215

£215

includes taxes & fees

26 Oct - 27 Oct

Charming Coastal/Country Home w/3 Acres & Sauna!

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

A living room with a grey sofa, two lamps, a coffee table, and a TV.

A hallway with a wooden floor, a white door with a black frame, and a small window at the end.

An outdoor patio with a round table and chairs, a yellow umbrella, and a wooden deck.

4. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach

9.6 out of 10, Exceptional, (30 reviews)

9.6/10

Exceptional

(30 reviews)

"Wonderful place to visit "

James L.

The price is £226

£226

includes taxes & fees

29 Oct - 30 Oct

The Cozy Crab- Your Charming Haven in Lovely North Beach!

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

A kitchen with a stove, sink, and dining area with chairs and a table.

A two-story house with a red roof, white siding, and red shutters.

A park with swings, a bench, and a view of a body of water.

5. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views

Deale

The price is £330

£330

includes taxes & fees

27 Oct - 28 Oct

3-bedroom house in Deale located on Bay many amenities and great views

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

A two-story house with a porch, a white picket fence, and blooming pink trees.

A dining area with a wooden table and chairs, a patterned rug, and a staircase leading to another level.

A pier with a wooden walkway, a sandy beach, and a dog on a leash.

6. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

10.0 out of 10, Exceptional, (40 reviews)

10/10

Exceptional

(40 reviews)

"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."

Sarah

The price is £330

£330

includes taxes & fees

26 Oct - 27 Oct

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

A deck with outdoor furniture, a red door, and a house with windows.

A living room with a sofa, ottoman, TV, and dining area with chairs and a table.

A bedroom with a bed, a window with curtains, a radiator, and a mirror.

A modern kitchen with wooden cabinets, stainless steel appliances, a round dining table with stools, and a ceiling fan.

7. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"

David S.

The price is £282

£282

includes taxes & fees

18 Nov - 19 Nov

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

A bedroom with a bed, a ceiling fan, a window, and a view of the outdoors.

A single-story house with a front porch, a chimney, and a green door.

A modern kitchen with white cabinetry, a built-in oven, a microwave, and a coffee maker.

8. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

10.0 out of 10, Exceptional, (17 reviews)

10/10

Exceptional

(17 reviews)

"very serene, peaceful home on the bay! Amazing getaway! "

Jill C.

The price is £388

£388

includes taxes & fees

25 Oct - 26 Oct

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

A two-story house with a red roof, a brick chimney, and a small porch.

A hallway with wooden flooring, a colorful rug, a potted plant, a wall-mounted wooden art piece, and a door leading to another room.

A spacious living room with a sectional sofa, a fireplace, and a sliding glass door leading to a balcony.

A grassy area with a body of water, a wooden fence, and a white building in the background.

9. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

8.4 out of 10, Very good, (6 reviews)

8.4/10

Very good

(6 reviews)

"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...

Michele F.

The price is £781

£781

includes taxes & fees

26 Oct - 27 Oct

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Three birds perched on a wooden structure by the water.

KI Beach House has many Great Rooms for Mingling or just being by yourself.

A beach with thatched umbrellas and tables, a wooden fence, and a sunset in the background.

A wooden deck with picnic tables and umbrellas, a covered seating area with chairs, and a house with large windows.

10. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

10.0 out of 10, Exceptional, (75 reviews)

10/10

Exceptional

(75 reviews)

"Just what was needed for our weekend stay."

barbara s.

The price is £1,022

£1,022

includes taxes & fees

26 Oct - 27 Oct

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

A beach with chairs and a pier in the background.

A living room with a sofa, coffee table, and a ceiling fan. There is a staircase with a railing leading to an upper level.

A restaurant interior with tables, chairs, and a green dinosaur-shaped salt shaker.

An aerial view of a marina with boats docked, surrounded by residential buildings and lush greenery.

11. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

9.6 out of 10, Exceptional, (19 reviews)

9.6/10

Exceptional

(19 reviews)

"The perfect off-season get-away! "

Pamela B.

The price is £398

£398

includes taxes & fees

3 Nov - 4 Nov

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

A calm lake with a wooden dock extending into the water, surrounded by trees and buildings in the background.

A spacious living room with a fireplace, a round wooden dining table with chairs, a sofa, and a large window offering a view of a lake.

A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

12. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!

Shady Side

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."

Michelle H.

The price is £365

£365

includes taxes & fees

10 Nov - 11 Nov

Sunset Cottage - West River Access and Views!

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

A cozy living room with a sofa, chairs, a coffee table, and a patterned rug.

A spacious kitchen with a central island, wooden cabinets, and a dining area with a table and chairs.

A kitchen with white cabinets, a central island with stools, a dining area with a table and chairs, and a view through the glass doors.

13. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

10.0 out of 10, Exceptional, (43 reviews)

10/10

Exceptional

(43 reviews)

"Fantastic, property, location and positive interaction with owner."

David R.

The price is £1,008

£1,008

includes taxes & fees

26 Oct - 27 Oct

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

A modern kitchen with white cabinets, stainless steel appliances, a window with a view, and a teal chair.

A house with a red door, a small front yard with a pathway, and a bush with pink flowers.

A modern living room with a sofa, a coffee table with flowers, a kitchen area with a refrigerator, and a dining table with chairs.

14. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10

Edgewater

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"House was clean and comfortable. Great layout. "

Kristin G.

The price is £525

£525

includes taxes & fees

22 Oct - 23 Oct

Family Home on Mayo Peninsula | Deck | Sleeps 10

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

A staircase with wooden steps leading to an upper floor, a blue rug with a white pattern at the bottom, and a wall-mounted surfboard rack.

A modern living room with a sectional sofa, a wooden coffee table, a fireplace, and a brick accent wall.

A modern kitchen with white countertops, wooden cabinets, and stainless steel appliances. There is a dining area with a glass table and chairs, and a view of the outdoors through large windows.

15. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Great house in cute neighborhood. Thanks for a very comfortable stay!"

Paul C.

The price is £415

£415

includes taxes & fees

17 Nov - 18 Nov

Annapolis Retreat - 7 mins from downtown Annapolis!

A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

A kitchen with white cabinets, a granite countertop, and three stools.

A living room with a sofa, ottoman, and a coffee table. There is a ladder leaning against the wall and a door leading to a balcony.

A calm waterfront with docked boats, a clear sky, and houses in the background.

16. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly

Edgewater

9.8 out of 10, Exceptional, (13 reviews)

9.8/10

Exceptional

(13 reviews)

"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "

Diane D.

The price is £406

£406

includes taxes & fees

22 Oct - 23 Oct

Renovated Bungalow | Walk to Beach | Dog-Friendly

A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

A multi-story building with a central staircase, outdoor seating area, and potted plants.

A spacious living room with a blue wall, wooden flooring, a glass display cabinet, and a dining area with a table and chairs.

A dining area with a table and chairs, a bookshelf, and a view of the outdoors.

17. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat

Dorchester County

10.0 out of 10, Exceptional, (45 reviews)

10/10

Exceptional

(45 reviews)

"Comfortable, roomy, awesome views!"

John C.

The price is £244

£244

includes taxes & fees

17 Nov - 18 Nov

Sunset Breezes - quiet waterfront retreat

A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

A living room with a sofa, a dining table with placemats, a basket of oranges, and a staircase.

An outdoor dining area with wooden tables and chairs, surrounded by greenery and a large tree.

A brick building with a white porch and a well-maintained lawn.

18. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

9.4 out of 10, Exceptional, (26 reviews)

9.4/10

Exceptional

(26 reviews)

"Pet friendly!"

Mary Beth S.

The price is £300

£300

includes taxes & fees

21 Nov - 22 Nov

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

A wooden dock extending into a calm body of water with boats docked at the end.

A modern living room with a white sofa, a coffee table, and a dining area with a wooden table and chairs.

A modern living room with a white sofa, a coffee table, and a potted plant.

A kitchen with wooden flooring, stainless steel appliances, a white door, and a white dining table with chairs.

19. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

Historic District

10.0 out of 10, Exceptional, (86 reviews)

10/10

Exceptional

(86 reviews)

"Location, amenities, cleanliness, parking all great!"

Nancy N.

The price is £360

£360

includes taxes & fees

16 Nov - 17 Nov

Cozy 2br home w/ parking in downtown Annapolis

An outdoor patio with a table and chairs, a large umbrella, and a view of a garden and trees.

A spacious room with a large sliding glass door leading to a balcony, a wooden rocking chair, and a cabinet with drawers.

A marina with multiple boats docked at wooden piers, surrounded by buildings and trees.

A bedroom with a bed, a ceiling fan, a window with curtains, and a dresser.

20. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis

Hillsmere

The price is £314

£314

includes taxes & fees

29 Oct - 30 Oct

The Harness Creek Retreat in Annapolis

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Sherwood Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"Esperaba mas de este hotel. Aun asi no esta mal."

Christian 2-night trip

Posted 6 hours ago

DoubleTree by Hilton Hotel Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent

"I was very pleased with the amenities, room size, cleanliness of the room. There were plenty of towel, blankets and shower items to make the stay warm and pleasant. Breakfast was delicious with lots of choices."

Ann Christine 2-night trip

Posted 12 hours ago

Sonesta ES Suites Annapolis

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Great location, hotel super clean and good restaraunt . Short walking distance to great shopping and many more bars and restaraunts"

Robin 1-night trip

Posted 1 day ago

Annapolis Waterfront Hotel, Autograph Collection

Knapps Narrows Marina & Inn

8/10 Good

"Property is very clean with beautiful views. Property very close to Tilghman island as quick walk over the bridge to get on the island. Restaurant also within walking distance."

Jim 1-night trip

Posted 1 day ago

Knapps Narrows Marina & Inn

Best Western Annapolis

10/10 Excellent

"Super nice staff, Clean rooms, comfortable bed, good breakfast and close to restaurants and less than 5miles to City Dock. I was in Annapolis for work for 5 days, I recommend this hotel, thank you!"

Teri 5-night trip

Posted 1 day ago

Best Western Annapolis

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Wonderful staff! Had a problem getting into the bed because it was too high and I was too short. They were wonderful with accommodating my needs! They moved me to a new room and location!"

Katherine 2-night trip

Posted 2 days ago

The Inn at Chesapeake Bay Beach Club

Rod 'N' Reel Resort

10/10 Excellent

"Loved the balcony."

Hildehardo F 4-night trip

Posted 2 days ago

Rod 'N' Reel Resort

Hyatt Regency Chesapeake Bay

8/10 Good

"Nice place, dinner staff was super slow but overall nice stay"

Richard 1-night trip

Posted 2 days ago

Hyatt Regency Chesapeake Bay

Find out more about Sherwood

Sherwood Holiday Homes information

Number of reviews	471
Accommodation	584 Holiday Homes
Lowest Price	£215
Highest Price	£1,022

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Sherwood on Expedia.com

Search Holiday Homes in Sherwood

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sherwood holiday homes

1. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

2. Beachside Oasis with Beach Passes & King Suite by A Haven Away

3. Charming Coastal/Country Home w/3 Acres & Sauna!

4. The Cozy Crab- Your Charming Haven in Lovely North Beach!

5. 3-bedroom house in Deale located on Bay many amenities and great views

6. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

7. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

8. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

9. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

10. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

11. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

12. Sunset Cottage - West River Access and Views!

13. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

14. Family Home on Mayo Peninsula | Deck | Sleeps 10

15. Annapolis Retreat - 7 mins from downtown Annapolis!

16. Renovated Bungalow | Walk to Beach | Dog-Friendly

17. Sunset Breezes - quiet waterfront retreat

18. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

19. Cozy 2br home w/ parking in downtown Annapolis

20. The Harness Creek Retreat in Annapolis

Find holiday rentals that suit your style

Top Sherwood Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

Find out more about Sherwood

Sherwood Holiday Homes information

Explore a world of travel with Expedia

8. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8