Search Vacation Homes in Sherwood

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Homes in Sherwood

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
9.6 out of 10, Exceptional, (19)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
The price is AED 496
AED 1,254 total
includes taxes & fees
18 Nov - 19 Nov
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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

Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is AED 270
AED 932 total
includes taxes & fees
19 Nov - 20 Nov
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (42)
"Wonderful home and host. Very easy to check-in and communication was excellent. "
United States
Ann T.
The price is AED 228
AED 891 total
includes taxes & fees
18 Nov - 19 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview

Waterfront Getaway with Dock

Woolford
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
The price is AED 845
AED 1,024 total
includes taxes & fees
18 Nov - 19 Nov
Waterfront Getaway with Dock

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Wonderful stay. The Crab Shack and dock were the highlights. We spent most of our time there. It was awesome. Highly recommend. "
United States
Christopher D.
The price is AED 595
AED 1,390 total
includes taxes & fees
30 Nov - 1 Dec
Beautiful Waterfront Retreat in Cambridge!

Walk to Beach! King Bed & Free Beach Passes

North Beach
10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is AED 361
AED 1,267 total
includes taxes & fees
18 Nov - 19 Nov
Walk to Beach! King Bed & Free Beach Passes

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

Grasonville
9.6 out of 10, Exceptional, (12)
"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 AED 918
AED 1,538 total
includes taxes & fees
18 Nov - 19 Nov
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Prince Frederick
9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is AED 606
AED 1,273 total
includes taxes & fees
24 Nov - 25 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is AED 529
AED 1,574 total
includes taxes & fees
18 Nov - 19 Nov
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis
10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
The price is AED 764
AED 1,938 total
includes taxes & fees
18 Nov - 19 Nov
Charming Pet-Friendly Stay - Near Bay & Beaches.

Family Beach House: Spacious Deck, Grill & Views

Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AED 540
AED 1,521 total
includes taxes & fees
18 Dec - 19 Dec
Family Beach House: Spacious Deck, Grill & Views

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

Arundel on the Bay
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is AED 727
AED 1,780 total
includes taxes & fees
19 Nov - 20 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Cozy 2br home w/ parking in downtown Annapolis

Historic District
10.0 out of 10, Exceptional, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
The price is AED 496
AED 1,214 total
includes taxes & fees
10 Dec - 11 Dec
Cozy 2br home w/ parking in downtown Annapolis

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater
9.8 out of 10, Exceptional, (24)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
The price is AED 672
AED 2,033 total
includes taxes & fees
19 Nov - 20 Nov
Edgewater/Mayo Gateaway w/ Hot Tub

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

North Beach
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AED 532
AED 1,706 total
includes taxes & fees
3 Dec - 4 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Eastport Private Suite – 1 mi to USNA & Downtown, Near Boat Shows & Comm Week

Eastport
The price is AED 203
AED 558 total
includes taxes & fees
24 Nov - 25 Nov
Eastport Private Suite – 1 mi to USNA & Downtown, Near Boat Shows & Comm Week

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

Homewood
9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
The price is AED 744
AED 1,765 total
includes taxes & fees
18 Nov - 19 Nov
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Fisher House: Steps From USNA + Covered Parking!

Historic District
10.0 out of 10, Exceptional, (13)
"The location is perfect!"
United States
suzanne d.
The price is AED 1,179
AED 2,688 total
includes taxes & fees
1 Dec - 2 Dec
Fisher House: Steps From USNA + Covered Parking!

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

Prince Frederick
10.0 out of 10, Exceptional, (8)
"Clean and easy "
United States
Robert R.
The price is AED 588
AED 1,254 total
includes taxes & fees
24 Nov - 25 Nov
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere
10.0 out of 10, Exceptional, (4)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AED 680
AED 2,035 total
includes taxes & fees
2 Dec - 3 Dec
Annapolis Retreat - 7 mins from downtown Annapolis!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sherwood Hotel Reviews