
Sherwood Vacation Packages
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Your Sherwood Vacation
When you organize a vacation package to Sherwood, you can relax and enjoy your getaway knowing that all your travel arrangements have been made in advance. Discover the charms of this vibrant city while based in a neighborhood like Deale Beach, which is good for walking. A trip to Sherwood is an excellent opportunity to take in the sights. Check out renowned attractions like St. Michaels Winery, Chesapeake Bay Maritime Museum and Tilghman Watermen’s Museum. Whoever you're escaping with and whatever your bank balance, your dream Sherwood vacation is only clicks away with Expedia.
Top Sherwood Vacation Deals
Price found within the past 48 hours. Click for updated prices.


Beach Walk
Downtown Ocean City
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
7.6/10 Good! (65 reviews)
PROS:
*The location is less than a minute walk to the boardwalk
*The staff was helpful during hours; in the evening and night we had to wait till the next day for help
*There is a working kitchen with a regular fridge, mini fridge, gas stove, dishwasher, microwave, toaster and coffee pot. Some dishes are provided. While there was soap supplied, no dish sponge or cloth was available
*The table seats 8 and around the bar of the kitchen seats 6.
CONS:
*Even in the apartment that sleeps 14, you are only given 1 parking pass.
*There was mold under one of the bathroom sinks.
*The master bath's shower pressure was terrible.
*Parts of the house are rough (a closet door was hanging off and just leaning against the frame)
*They ask you not to hang things over the porch railings, but there isn't anywhere to dry wet clothes.
*No washer/dryer
*Lobby is upstairs; people walked in on us
HOUSE LAYOUT:
-Bedroom 1 is in the living room, as soon as you walk through the front door; 2-twin trindle beds and a television.
-Bedroom 2 has a queen and a twin with a connected bathroom, shower, toilet, and sink.
*Full bathroom in hallway
-Bedroom 3 has 2 queens with a television
-Bedroom 4 has a queen bed with an attached bathroom, toilet and sink only.
-Bedroom 5 has a king size bed with an attached bathroom that has a toilet, sink and large shower stall with seat.
PARKING:
Parking is on a corner lot and there is an overflow lot, with directions on parking pass.
Parking on 11th St and on is free
Reviewed on Jul. 14, 2025


Americana Motor Inn
Downtown Ocean City
per person
Oct 2 - Oct 6
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.4/10 Very Good! (772 reviews)
The Americana Inn is a hidden gem, is clean, affordable, and right off the boardwalk. The staff was kind and helpful.
Reviewed on Jul. 21, 2025
Sherwood Hotel Deals

Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Aug 3 to Aug 4
CA $139
CA $205 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,809 reviews)
"Overall it is a great hotel to stay, close to all activities"
Reviewed on Jul. 23, 2025

Graduate by Hilton Annapolis
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Aug 3 to Aug 4
CA $211
CA $241 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Excellent!"
Reviewed on Jul. 21, 2025

DoubleTree by Hilton Hotel Annapolis
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Aug 3 to Aug 4
CA $134
CA $153 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (1,010 reviews)
"The staff was very attentive and helpful. The restaurant and bar in the hotel was a delight."
Reviewed on Jul. 22, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.