Deals on vacations and trips to Sherwood

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Sherwood flight + hotel vacation packages

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Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
per person
Jul 27 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
This hotel features free self parking and express check-in. Express check-out is also provided.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Jul 27 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. Dry cleaning is also provided.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Jul 27 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
This hotel features 4 restaurants, an outdoor pool, and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.
The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
per person
Jul 27 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
This hotel features a restaurant and 2 bars/lounges. Enjoy the indoor pool and perks like free WiFi. Self parking and a safe deposit box are also offered on site.
Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
per person
Jul 27 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.

Top Sherwood hotels deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
The price is $199 per night
$199
includes taxes & fees
$145 per night
May 25 - May 26
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.
Pet friendly
Free WiFi
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
The price is $183 per night
$183
includes taxes & fees
$161 per night
May 28 - May 29
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Pet friendly
Free WiFi
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
The price is $170 per night
$170
includes taxes & fees
$149 per night
May 8 - May 9
A full-service spa, a 24-hour gym, and a restaurant are all featured at this Beaux Arts hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and snack bar/deli.
Pool
Spa
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
The price is $125 per night
$125
includes taxes & fees
$110 per night
May 27 - May 28
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a snack bar/deli, and dry cleaning are also offered.
Pet friendly
Free WiFi
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
Free Cancellation
Reserve now, pay when you stay
The price is $159 per night
$159
includes taxes & fees
$143 per night
May 13 - May 14
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Pet friendly
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Free Cancellation
Reserve now, pay when you stay
The price is $310 per night
$310
includes taxes & fees
$273 per night
May 7 - May 8
This smoke-free resort features a private beach, a golf course, and a full-service spa. Bring the family and enjoy the children's club, mini golf, and children's pool. Enjoy the 2 outdoor pools and perks like free self parking and free WiFi.
On private beach
Pool
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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.

Popular places to visit

Back Creek Community Park

Back Creek Community Park is just one of the places to see in Sherwood, so why not enjoy the other things to explore during your travels? Wander the marina or discover the area's sunsets.

Back Creek Community Park

Goat Island

Commune with nature and explore the great outdoors at Goat Island during your travels in Sherwood. Wander the marina or discover the area's sunsets.

Goat Island

Photos of local treasures

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