Sherwood Vacations from $760

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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.
Comfort Inn Gold Coast

Comfort Inn Gold Coast

2.5 out of 5
North Ocean City
Price was $890, price is now $760 per person
$760
per person
May 11 - May 17
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.4/10 Very Good! (1,000 reviews)
Clean room. Quiet. Lots of parking

Reviewed on Feb 28, 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,199, price is now $922 per person
$922
per person
May 11 - May 17
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
9.4/10 Exceptional! (720 reviews)
Very clean, updated, with friendly staff.

Reviewed on Mar 6, 2026

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $1,031, price is now $820 per person
$820
per person
May 11 - May 17
found 3 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.6/10 Excellent! (1,154 reviews)
Love the ocean front rooms nice size balcony, best if you can get a end room, more windows

Reviewed on Mar 4, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $1,160, price is now $924 per person
$924
per person
May 11 - May 17
found 3 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
9/10 Wonderful! (3,444 reviews)
Room was clean, comfortable, 11th floor was a little bit too high for me. Next trip lower floor. Friendly staff

Reviewed on Feb 28, 2026

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $1,273, price is now $1,066 per person
$1,066
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
7.4/10 Good! (171 reviews)
Got better than what I expected for the price. Front desk ladies were happy & helpfully. Only thing that would be nice would be some type of dimmer lights for night, outlets near beds & softer beds. Will definately be staying here again! Full kitchen with full size fridge saved us $ not having to eat out. It's like a hotel sized condo.

Reviewed on Oct 1, 2025

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Sherwood Hotel Deals

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road Sherwood MD
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $99 total per night from Mar 8 to Mar 9
$99 total
Mar 8 - Mar 9
Total with taxes and fees
9.4/10 Exceptional! (371 reviews)
The staff were very accommodating for our late check-in. The room was clean, the view was beautiful. It was only an overnight trip but I can't wait to come back when it's warmer.

Reviewed on Mar 4, 2026

Knapps Narrows Marina & Inn
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
$157 nightly
The price is $179 total per night from Apr 2 to Apr 3
$179 total
Apr 2 - Apr 3
Total with taxes and fees
9/10 Wonderful! (1,880 reviews)
Staff were a pleasure. Room was beautiful.

Reviewed on Mar 4, 2026

Historic Inns of 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
$89 nightly
The price is $102 total per night from Mar 15 to Mar 16
$102 total
Mar 15 - Mar 16
Total with taxes and fees
8.6/10 Excellent! (1,014 reviews)
I stayed here as I did a visit for my youngest son who is attending Bowie. While I stayed most of the time on campus, I found when I was at the hotel I found the staff and facility both inviting, warm and cordial.

Reviewed on Mar 5, 2026

DoubleTree by Hilton Hotel Annapolis
See all 1,156 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 $760 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.