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

Holiday Homes in Sherwood

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is NZ$466
includes taxes & fees
30 Aug - 31 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is NZ$527
includes taxes & fees
3 Sept - 4 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

3. 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, (37 reviews)
"Such a great house! "
United States
Stephanie V.
The price is NZ$752
includes taxes & fees
31 Aug - 1 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

4. 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, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is NZ$587
includes taxes & fees
30 Aug - 31 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A deck with outdoor furniture, a red door, and a house with siding.

5. 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
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is NZ$414
includes taxes & fees
1 Sept - 2 Sept
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

6. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is NZ$892
includes taxes & fees
7 Sept - 8 Sept
Sunset Cottage - West River Access and Views!

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is NZ$762
includes taxes & fees
1 Sept - 2 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (15 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is NZ$988
includes taxes & fees
2 Sept - 3 Sept
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

9. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is NZ$845
includes taxes & fees
31 Aug - 1 Sept
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

10. 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 NZ$850
includes taxes & fees
9 Sept - 10 Sept
3-bedroom house in Deale located on Bay many amenities and great views
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

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

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is NZ$705
includes taxes & fees
1 Sept - 2 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is NZ$1,164
includes taxes & fees
29 Aug - 30 Aug
Family Home on Mayo Peninsula | Deck | Sleeps 10
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

13. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is NZ$769
includes taxes & fees
9 Sept - 10 Sept
Plum Point Cottage #17
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is NZ$972
includes taxes & fees
2 Sept - 3 Sept
Renovated Bungalow | Walk to Beach | Dog-Friendly
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

15. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is NZ$974
includes taxes & fees
9 Sept - 10 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

16. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (76 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is NZ$1,126
includes taxes & fees
21 Sept - 22 Sept
Charming Annapolis WaterVIEW Home
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

17. 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, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is NZ$685
includes taxes & fees
1 Sept - 2 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A two-story house with a red roof, a brick chimney, and a small porch.

18. 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
6.8 out of 10, (3 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveller
The price is NZ$1,757
includes taxes & fees
3 Sept - 4 Sept
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

19. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (3 reviews)
"N"
United States
Maria S.
The price is NZ$1,975
includes taxes & fees
30 Aug - 31 Aug
Waterfront Escape with Pool Nature Lover Paradise
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Location is great! Thank you."
Patrick 2-night trip
Posted 11 hours ago
Crowne Plaza Annapolis by IHG

Find out more about Sherwood

Sherwood Holiday Homes information

Number of reviews
209
Accommodation
620 Holiday Homes
Lowest Price
NZ$414
Highest Price
NZ$1,975