Sherwood Vacations from $696
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The Latest Sherwood Vacation Packages
- Fenwick Shores, Tapestry Collection by Hilton
Sep 30 - Oct 3Fenwick Shores, Tapestry Collection by Hilton + Flight
Fenwick Island3 nights3.5 star property9.4/10 - Exceptional (802 reviews)"Modern, clean, well-kept, comfy, quiet, close to beach."Reviewed July 19, 2026Roundtrip • Philadelphia (PHL) - Salisbury (SBY)PHL - SBY • Nonstop SBY - PHL • Nonstop$843$696found 17 hours agoper traveler - Sea Breeze Inn
Sep 22 - Sep 26Sea Breeze Inn + Flight
Downtown Ocean City4 nights2.0 star property6.6/10 - (30 reviews)"Not at all what I expected based on photos and reviews. Property needs A LOT of renovation and mold remediation done as I had a broken taped up window in the bathroom and mold in the shower. Appliances in the rooms need to be cleaned and/or updated as well. All rooms should have the same size TVs. I had 2 rooms, 1 with a 32-36in TV and the other with a 17in TV practically a computer screen. Pricing was good to be a block from the boardwalk but you definitely get what you pay for and I don’t mean..."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 2 hours agoper traveler - Ocean 1 Hotel and Suites
Sep 30 - Oct 3Ocean 1 Hotel and Suites + Flight
Downtown Ocean City3 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 • Philadelphia (PHL) - Salisbury (SBY)PHL - SBY • Nonstop SBY - PHL • Nonstop$1,099$901found 17 hours agoper traveler - Carousel Resort Hotel & Condominiums
Sep 3 - Sep 7Carousel Resort Hotel & Condominiums + Flight
North Ocean City4 nights3.0 star property7.8/10 - Good (1,415 reviews)"I was disappointed that my ocean front view was actually st for the patio behind the pool and chairs. So I paid 33o more to upgrade to a higher floor. Then we discovered that the elevator had been out of service for weeks and most of the staff did not understand English. 4 sets of stairs for a couple in their 702 was difficult. One of the activities was a smores event, but no one was informed upfront that each smore kit was $7."Reviewed July 18, 2026Roundtrip • New York (JFK) - Salisbury (SBY)JFK - SBY • 1 stop SBY - JFK • 2 stops$1,670$1,389found 2 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 $696 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.