Holiday Homes in Sherwood

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Our top choices for Sherwood holiday homes

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is AU$585
includes taxes & fees
6 Apr - 7 Apr
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is AU$394
includes taxes & fees
5 Apr - 6 Apr
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AU$408
includes taxes & fees
8 Apr - 9 Apr
Charming Coastal/Country Home w/3 Acres & Sauna!

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, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$606
includes taxes & fees
6 Apr - 7 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AU$630
includes taxes & fees
8 Apr - 9 Apr
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

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 AU$681
includes taxes & fees
7 Apr - 8 Apr
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is AU$527
includes taxes & fees
14 Apr - 15 Apr
Walk to Beach! King Bed & Free Beach Passes

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (43 reviews)
"Clean, quiet, comfy"
United Kingdom
Deborah V.
Sunset Breezes - quiet waterfront retreat

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
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is AU$605
includes taxes & fees
14 Apr - 15 Apr
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is AU$867
includes taxes & fees
5 Apr - 6 Apr
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is AU$719
includes taxes & fees
7 Apr - 8 Apr
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is AU$767
includes taxes & fees
5 Apr - 6 Apr
Charming Pet-Friendly Stay - Near Bay & Beaches.

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, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AU$684
includes taxes & fees
20 Apr - 21 Apr
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (54 reviews)
"Great place, will stay again"
United States
Matt S.
The price is AU$396
includes taxes & fees
21 Apr - 22 Apr
Waterfront Getaway with Dock

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, (13 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AU$902
includes taxes & fees
28 Apr - 29 Apr
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is AU$747
includes taxes & fees
6 Apr - 7 Apr
Cute bungalow blocks to Stadium

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 AU$763
includes taxes & fees
27 Apr - 28 Apr
Annapolis Retreat - 7 mins from downtown Annapolis!

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (1 review)
"Beautiful home for a girls weekend away. The view is spectacular, host was communicative, and lots of thoughtful small touches throughout the home and the experience. Thank you for a wonderful stay! "
United States
Katie K.
The price is AU$637
includes taxes & fees
14 Apr - 15 Apr
Sunset Cottage - West River Access and Views!

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is AU$871
includes taxes & fees
6 Apr - 7 Apr
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is AU$1,029
includes taxes & fees
6 Apr - 7 Apr
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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

Find out more about Sherwood

Sherwood Holiday Homes information

Number of reviews
346
Accommodation
564 Holiday Homes
Lowest Price
AU$394
Highest Price
AU$1,029