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

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Sherwood vacation 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, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is ￥12,723
￥44,058 total
includes taxes & fees
Nov 1 - Nov 2
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

2. 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)
"Wonderful place to visit "
United States
James L.
The price is ￥22,877
￥51,175 total
includes taxes & fees
Oct 30 - Oct 31
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

3. 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
10.0 out of 10, Exceptional, (1 review)
"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...
United States
Amelia
The price is ￥28,399
￥72,123 total
includes taxes & fees
Nov 1 - Nov 2
3-bedroom house in Deale located on Bay many amenities and great views
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is ￥14,313
￥45,656 total
includes taxes & fees
Nov 2 - Nov 3
Charming Coastal/Country Home w/3 Acres & Sauna!
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

5. 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, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is ￥16,635
￥54,254 total
includes taxes & fees
Nov 1 - Nov 2
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

6. 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)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is ￥38,946
￥75,279 total
includes taxes & fees
Oct 30 - Oct 31
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A deck with outdoor furniture, a red door, and a house with windows.

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)
"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!"
United States
David S.
The price is ￥26,979
￥59,533 total
includes taxes & fees
Nov 8 - Nov 9
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.

8. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 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."
United States
Michelle H.
The price is ￥31,554
￥71,063 total
includes taxes & fees
Nov 4 - Nov 5
Sunset Cottage - West River Access and Views!
Three birds perched on a wooden structure by the water.

9. 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)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is ￥126,058
￥218,718 total
includes taxes & fees
Nov 1 - Nov 2
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

10. 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)
"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."
United States
Sarah
The price is ￥30,749
￥81,292 total
includes taxes & fees
Nov 16 - Nov 17
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A beach with chairs and a pier in the background.

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)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is ￥30,571
￥75,916 total
includes taxes & fees
Nov 3 - Nov 4
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A two-story house with a red roof, a brick chimney, and a small porch.

12. 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)
"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...
United States
Michele F.
The price is ￥113,594
￥166,232 total
includes taxes & fees
Oct 30 - Oct 31
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

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, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is ￥126,058
￥218,718 total
includes taxes & fees
Nov 2 - Nov 3
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.

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)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is ￥38,196
￥110,811 total
includes taxes & fees
Nov 1 - Nov 2
Family Home on Mayo Peninsula | Deck | Sleeps 10
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 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 ￥30,387
￥87,520 total
includes taxes & fees
Oct 30 - Oct 31
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.

16. 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 ￥34,078
￥92,986 total
includes taxes & fees
Nov 9 - Nov 10
Annapolis Retreat - 7 mins from downtown Annapolis!
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

17. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
The price is ￥17,118
￥48,749 total
includes taxes & fees
Nov 2 - Nov 3
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

18. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
Sunset Breezes - quiet waterfront retreat
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

19. 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)
"Pet friendly!"
United States
Mary Beth S.
The price is ￥26,821
￥61,209 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A marina with boats docked, a water tower, and residential buildings with balconies.

20. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
Cambridge
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wouldn't hesitate to come back and stay for a few days. Beautiful home overlooking the docks."
United States
mike
The price is ￥35,498
￥76,444 total
includes taxes & fees
Nov 1 - Nov 2
Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Our stay was much better than I was expecting! The area was very quiet and the staff friendly and helpful. Continental breakfast was your standard fare and everything clean."
Bobbi 2-night trip
Posted 4 hours ago
St Michaels Inn

Find out more about Sherwood

Sherwood Vacation Homes information

Number of reviews
407
Accommodation
595 Vacation Homes
Lowest Price
￥44,058
Highest Price
￥218,718