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The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
per person
Jul 17 - Jul 20
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.
Club Ocean Villas II

Club Ocean Villas II

3.5 out of 5
North Ocean City
Save 100% on your flight
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Salisbury (SBY)
A marina and an indoor pool are featured at this smoke-free apartment. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like a picnic area and a virtual front desk.
Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
North Ocean City
Save 100% on your flight
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Salisbury (SBY)
This traditional hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at the beach bar and enjoy perks like free WiFi.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Save 100% on your flight
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Salisbury (SBY)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Dine at the beachfront restaurant and relax with beach umbrellas. Family-friendly amenities include an arcade/game room and kid-friendly dining, along with volleyball.
Atlantic Oceanside Dewey

Atlantic Oceanside Dewey

2.5 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Salisbury (SBY)
This hotel features a seasonal outdoor pool and a rooftop terrace. WiFi in public areas is free. Self parking, a coffee shop, and a grocery/convenience store are also offered.

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
$169 nightly
The price is $193 total per night
$193 total
Jun 10 - Jun 11
Total includes taxes and fees
This hotel features 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
$152 nightly
The price is $174 total per night
$174 total
Jun 8 - Jun 9
Total includes taxes and fees
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
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
$281 nightly
The price is $319 total per night
$319 total
Jun 22 - Jun 23
Total includes taxes and fees
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
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
$143 nightly
The price is $159 total per night
$159 total
Jun 9 - Jun 10
Total includes taxes and fees
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
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
$93 nightly
The price is $106 total per night
$106 total
Jun 15 - Jun 16
Total includes taxes and fees
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
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $118 total per night
$118 total
Jun 4 - Jun 5
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.
Pet friendly
Parking included
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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

Browse Sherwood vacation photos for more inspiration