Sherwood Holiday Homes from €246: Search Top 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 holiday homes

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

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

Stevensville

Dawn G.

includes taxes & fees

28 Sept - 29 Sept

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

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

Stevensville

Michelle P.

includes taxes & fees

28 Sept - 29 Sept

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

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

North Beach

Johanna S.

includes taxes & fees

27 Sept - 28 Sept

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

4. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

includes taxes & fees

21 Oct - 22 Oct

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

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

North Beach

Penny N.

includes taxes & fees

29 Sept - 30 Sept

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Sharon Z.

includes taxes & fees

28 Sept - 29 Sept

A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

7. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

Robin

includes taxes & fees

28 Sept - 29 Sept

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

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

Cambridge

Jill C.

includes taxes & fees

26 Oct - 27 Oct

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

9. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

David S.

includes taxes & fees

21 Oct - 22 Oct

A market with a covered seating area and a sign indicating parking for curbside pickup.

10. Rose Haven Coastal Cottage

North Beach

Sharon t.

includes taxes & fees

28 Sept - 29 Sept

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

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

Cambridge

Robert

includes taxes & fees

12 Oct - 13 Oct

A living room with two brown leather sofas, a wooden side table with a lamp, a small shelf with plants, and a painting of a tree.

12. More, than just a place to sleep - welcome home!

Cambridge

includes taxes & fees

8 Oct - 9 Oct

13. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Chesapeak beach

Bryan P.

includes taxes & fees

26 Oct - 27 Oct

A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

14. Plum Point Cottage #17

Huntingtown

includes taxes & fees

26 Sept - 27 Sept

A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

15. Waterfront Getaway with Dock

Woolford

Meagan G.

includes taxes & fees

4 Oct - 5 Oct

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

16. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

includes taxes & fees

6 Oct - 7 Oct

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

17. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

"We arrived and the air conditioning was broken.The owner did not inform us but installed portable AC’s running vents out of doors that would not close or lock. The old AC unit was installed incorrectly &BR below flooded by 12 am. contacted owner and then was told not to run AC & we would be refunded. Covered mattresses that were being soaked, cleaned up flood, washed all bedding. Owner said trying to find us another rental but there were none & I had service dog. If we moved we would miss...

Suzanne R.

includes taxes & fees

27 Sept - 28 Sept

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

18. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

20 Oct - 21 Oct

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

19. Sunset Breezes - quiet waterfront retreat

Dorchester County

John C.

includes taxes & fees

27 Sept - 28 Sept

Three birds perched on a wooden structure by the water.

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

Stevensville

barbara s.

includes taxes & fees

27 Sept - 28 Sept

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Top Sherwood Hotel Reviews

Sonesta ES Suites Annapolis

8/10 Good

"Good value for the money. Older property and there’s nothing special about it. Comfortable bed; limited cable TV package. Pretty good breakfast included, with free parking. It was cool in the morning and the breakfast room needed a little heat; instead they actually turned the a/c on which made the room too cool. This is my only complaint. Good for short stays."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."

Find out more about Sherwood

Sherwood Holiday Homes information

Number of reviews	274
Accommodation	501 Holiday Homes
Lowest Price	€246
Highest Price	€1,156

Room 1

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

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

4. 3-bedroom house in Deale located on Bay many amenities and great views

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

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

7. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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