Sherwood Vacations from $1,463

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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.
Hampton Inn & Suites Ocean City West

Hampton Inn & Suites Ocean City West

2.5 out of 5
West Ocean City
Price was $1,753, price is now $1,463 per person
$1,463
per person
Oct 3 - Oct 6
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
9.2/10 Wonderful! (719 reviews)
Very nice room , clean , will be back

Reviewed on Aug 24, 2025

Americana Motor Inn

Americana Motor Inn

2.5 out of 5
Downtown Ocean City
Price was $2,100, price is now $1,547 per person
$1,547
per person
Oct 3 - Oct 6
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
8.4/10 Very Good! (814 reviews)
We enjoyed being close to the boardwalk. Room was clean and served its purpose, nothing special but worked for our weekend stay. Loved having a balcony.

Reviewed on Aug 25, 2025

Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk

2.5 out of 5
Downtown Ocean City
Price was $2,700, price is now $2,111 per person
$2,111
per person
Oct 3 - Oct 6
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
9/10 Wonderful! (1,010 reviews)
Very nice and efficient staff

Reviewed on Aug 24, 2025

Tidelands Caribbean Hotel and Suites

Tidelands Caribbean Hotel and Suites

2.5 out of 5
Downtown Ocean City
Price was $1,885, price is now $1,498 per person
$1,498
per person
Oct 3 - Oct 6
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
6.8/10 (1,125 reviews)
We've stayed here before. Convenient to the Boardwalk. Check in staff wonderful! However, bath mat was torn and maid took our hand towels and didn't replace them. We asked for more and she said we have to wait for laundry? Front desk gave us 2 bath towels🙄. Cracks in ceramic towel. Phone didn't work. Needs definite updating!

Reviewed on Aug 24, 2025

Courtyard Ocean City Oceanfront

Courtyard Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $2,328, price is now $2,015 per person
$2,015
per person
Oct 3 - Oct 6
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
9/10 Wonderful! (948 reviews)
Most importantly, the room and bathroom were very clean. Staff members were nice and polite. Ocean front location was convenient. Excellent hotel overall.

Reviewed on Aug 16, 2025

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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
$143 nightly
The price is $163 total per night from Sep 8 to Sep 9
$163 total
Sep 8 - Sep 9
Total with taxes and fees
8.8/10 Excellent! (1,817 reviews)
"I just had the best birthday here. Perfect location, staff was amazing."

Reviewed on Aug 23, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $183 total per night from Sep 2 to Sep 3
$183 total
Sep 2 - Sep 3
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
"Very good"

Reviewed on Aug 20, 2025

Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $112 total per night from Aug 31 to Sep 1
$112 total
Aug 31 - Sep 1
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
"Where is the receipt"

Reviewed on Aug 19, 2025

DoubleTree by Hilton Hotel Annapolis
See all 1,190 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.

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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 $1,463 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.