Sherwood Vacations from $1,145

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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.

The Latest Sherwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $1,486, price is now $1,145 per person
$1,145
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
8.2/10 Very Good! (714 reviews)
Nice and clean. The staff is wonderful and very helpful.

Reviewed on Apr 19, 2026

Americana Motor Inn

Americana Motor Inn

2.5 out of 5
Downtown Ocean City
Price was $1,570, price is now $1,156 per person
$1,156
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
8.4/10 Very Good! (891 reviews)
parking was very tight because of some larger vehicles----the bathroom had no place to hang anything-----a few hooks on the door would be nice !!

Reviewed on May 4, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $1,821, price is now $1,380 per person
$1,380
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (3,531 reviews)
Great room, clean , excellent location

Reviewed on May 5, 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $2,472, price is now $1,899 per person
$1,899
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
9.6/10 Exceptional! (748 reviews)
If you think the Tapestry Collection implies a step above the usual accommodations at, say a Hampton Inn, think again. This place was closer to a Tru - very austere and disappointing. I do not believe that Hilton actively evaluates any of its labeled properties for conformance to any minimum standards - except possibly for those it owns directly which are most certainly the higher priced ones.

Reviewed on May 2, 2026

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Sherwood Hotel Deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $190 total per night from May 31 to Jun 1
$190 total
May 31 - Jun 1
Total with taxes and fees
9/10 Wonderful! (1,846 reviews)
Awesome as usual

Reviewed on May 6, 2026

Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
$110 nightly
The price is $125 total per night from May 24 to May 25
$125 total
May 24 - May 25
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
Do not accept a room facing the highway side. Road noise is terrible.

Reviewed on May 6, 2026

Crowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $113 total per night from May 24 to May 25
$113 total
May 24 - May 25
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
The room was exceptionally clean and well-appointed. The bed was comfortable and shower nice and hot. Breakfast was delicious with sufficient variety of offerings. The lobby is quite pretty and the staff helpful. Plenty of parking and the layout of the rooms made it feel less like a hotel, but more ...

Reviewed on May 5, 2026

Sonesta ES Suites Annapolis
See all 1,171 properties in Sherwood
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.

Find the Best Sherwood Vacation Packages

Sherwood Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
St. Michaels Winery, Bayside History Museum and Tilghman Watermen’s Museum

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Frequently asked questions

How much does a Sherwood vacation package cost?
You can snap up a vacation package to this destination from $1,145 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.

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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.