Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Find holiday rentals that suit your style
Apartments
Cottages
Our top choices for Sherwood holiday homes
1. Relax on Kent Island in 4 Bedroom Home w/Waterview
Relax on Kent Island in 4 Bedroom Home w/WaterviewStevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
Anthony P.
The price is €259
includes taxes & fees
15 Nov - 16 Nov
2. Beachside Oasis with Beach Passes & King Suite by A Haven Away
Beachside Oasis with Beach Passes & King Suite by A Haven AwayNorth Beach
10.0 out of 10, Exceptional, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
Johanna S.
The price is €279
includes taxes & fees
15 Nov - 16 Nov
3. 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"
Michael V.
The price is €293
includes taxes & fees
23 Nov - 24 Nov
4. 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 viewsDeale
10.0 out of 10, Exceptional, (2 reviews)
"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...
Amelia
The price is €398
includes taxes & fees
14 Nov - 15 Nov
5. 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 "
James L.
The price is €285
includes taxes & fees
16 Nov - 17 Nov
6. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, RestaurantsNorth Beach
10.0 out of 10, Exceptional, (41 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 €405
includes taxes & fees
16 Nov - 17 Nov
7. 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 parkingStevensville
8.6 out of 10, Excellent, (7 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."
Anonymous traveller
The price is €900
includes taxes & fees
21 Nov - 22 Nov
8. 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 AccessShady Side
9.4 out of 10, Exceptional, (3 reviews)
"the house was clean and fully stocked with all linens. there are some staples in the refrigerator and cabinets. All cookware and eatery are provided. there is only one grocery store in the area, so plan ahead. Fast food is not readily available. Nick responded quickly and thoroughly to all messages, that was great. It's a quiet neighborhood. It was the perfect place for a family and pet. we will return"
Jenny A.
The price is €324
includes taxes & fees
16 Nov - 17 Nov
9. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8Cambridge
10.0 out of 10, Exceptional, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
Jill C.
The price is €448
includes taxes & fees
19 Nov - 20 Nov
10. 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."
Michelle H.
The price is €389
includes taxes & fees
1 Dec - 2 Dec
11. 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)
"Great stay, exactly as advertised, Donna was great!"
Sam C.
The price is €1,134
includes taxes & fees
1 Dec - 2 Dec
12. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community BeachArundel 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!"
Ryan C.
The price is €428
includes taxes & fees
16 Nov - 17 Nov
13. Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Beach Front, Bay View, Fishing, chesapeake,Family GetawayChesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
Ben W.
The price is €361
includes taxes & fees
8 Dec - 9 Dec
14. 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."
David R.
The price is €1,138
includes taxes & fees
1 Dec - 2 Dec
15. Family Home on Mayo Peninsula | Deck | Sleeps 10
Family Home on Mayo Peninsula | Deck | Sleeps 10Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
Kristin G.
The price is €605
includes taxes & fees
14 Nov - 15 Nov
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!"
Paul C.
The price is €484
includes taxes & fees
30 Nov - 1 Dec
17. Family Friendly Cozy 3 Bedroom Duplex
Family Friendly Cozy 3 Bedroom DuplexGrasonville
The price is €279
includes taxes & fees
11 Dec - 12 Dec
18. Renovated Bungalow | Walk to Beach | Dog-Friendly
Renovated Bungalow | Walk to Beach | Dog-FriendlyEdgewater
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. "
Diane D.
The price is €474
includes taxes & fees
14 Nov - 15 Nov
19. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City MarinaCambridge
9.4 out of 10, Exceptional, (26 reviews)
"Pet friendly!"
Mary Beth S.
The price is €336
includes taxes & fees
13 Dec - 14 Dec
20. 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."
Sean B.
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.
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.
