Sherwood Vacations from $1,153
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The Latest Sherwood Vacation Packages
- Beach Walk
Sep 3 - Sep 7Beach Walk + Flight
Downtown Ocean City4 nights2.0 star property7.6/10 - Good (103 reviews)"Wonderful checkin. Fast. Nice. Big apt so we needed big parking. They accommodated us. Thankful. Did cut open foot on their old metal rusty chairs on porch, also sat in it and leg weekend and almost fell over. Cut is healing but was infected even after cleaning and cleaning. Kids could not be around those chairs with their little legs and feet also. We had to set one aside so no one would run into it. Great apt. Our family comes back every yr. Plenty of space. The wicker couch on porch leg was..."Reviewed July 10, 2026Roundtrip • New York (JFK) - Salisbury (SBY)JFK - SBY • 1 stop SBY - JFK • 2 stops$1,514$1,153found 16 hours agoper traveler - Sea Breeze Inn
Sep 22 - Sep 26Sea Breeze Inn + Flight
Downtown Ocean City4 nights2.0 star property6.8/10 - (31 reviews)"A diamond in the rough! Not pristine or glamorous and a little outdated, but it worked for a quick 3 day get away trip. The beds were very comfortable so it was easy to look past the outdated cosmetics of the room and bathroom. Love love love the location! It is absolutely perfect if you have small kids and want to be near the fun attractions OC has to offer. We have stayed here a few times and would definitely book again! Also, I really loved how they booked families with children all on one..."Reviewed July 20, 2026Roundtrip • Pittsburgh (PIT) - Salisbury (SBY)PIT - SBY • 1 stop SBY - PIT • 1 stop - Ocean Terrace Family Apartments
Sep 3 - Sep 7Ocean Terrace Family Apartments + Flight
Downtown Ocean City4 nights3.0 star property7.8/10 - Good (40 reviews)"Greatly enjoyed!!! Will stay again!!!"Reviewed July 11, 2026Roundtrip • New York (JFK) - Salisbury (SBY)JFK - SBY • 1 stop SBY - JFK • 2 stops$1,760$1,323found 16 hours agoper traveler - Empress Motel
Sep 3 - Sep 7Empress Motel + Flight
Downtown Ocean City4 nights2.0 star property7.8/10 - Good (175 reviews)"It was not clean. Restroom was really bad . Microwave didn’t work."Reviewed July 16, 2026Roundtrip • New York (JFK) - Salisbury (SBY)JFK - SBY • 1 stop SBY - JFK • 2 stops$1,607$1,218found 16 hours agoper traveler - Ocean 1 Hotel and Suites
Aug 20 - Aug 25Ocean 1 Hotel and Suites + Flight
Downtown Ocean City5 nights2.0 star property8.2/10 - Very Good (754 reviews)"Parking was a 1-2 blocks away. The spots were so tight the passenger had to get out before parking. Coffee pots were small and very dirty. Desk people were nice. It’s old but clean."Reviewed July 19, 2026Roundtrip • New York (NYC) - Salisbury (SBY)LGA - SBY • 2 stops SBY - LGA • 2 stops$1,508$1,164found 0 hours agoper traveler
Sherwood Hotel Deals
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & Suites
Frequently Asked Questions
How much does a Sherwood vacation package cost?
You can snap up a vacation package to this destination from $1,153 on Expedia. However, how much your vacation to Sherwood costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Sherwood?
November, December and January are great times to search for cheap Sherwood vacation packages. Opting to travel in quieter periods means you can usually find lower prices on flights and hotels.
How many days is enough for Sherwood?
Typically, a handful of days is enough to see the major attractions during your Sherwood vacation. However, if you'd like to have more time to relax or go on day trips, consider extending your trip.
How to find the best Sherwood package deals?
Finding a cheap Sherwood package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Sherwood package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Sherwood vacation as a package?
You can enjoy significant savings on your Sherwood break by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Sherwood?
If you have your Sherwood vacation dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Sherwood vacation packages?
Secure your dream trip to Sherwood with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until payday — we've partnered with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snap up travel deals while they last.