Sherwood Vacations from $599

Book a Hotel + Flight or Car together to unlock savings

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.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $669, price is now $599 per person
$599
per person
Feb 20 - Feb 23
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Salisbury (SBY)
9/10 Wonderful! (3,316 reviews)
All of the staff from front desk to bar to cleaning staff were very friendly Clean throughout and decorated beautifully for the Holidays

Reviewed on Dec 8, 2025

The Shore House

The Shore House

2 out of 5
West Ocean City
Price was $2,117, price is now $1,769 per person
$1,769
per person
Feb 20 - Feb 23
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Salisbury (SBY)
6.8/10 (598 reviews)
Overall it was perfect for country calling. There’s a shuttle at the hotel next door that we took everyday down to the entrance for $5 cash. The beds were comfortable, clean and the shower water was hot. I almost ended up cancelling though because during the off season it is nearly impossible to reach the hotel!! I called probably 10 times and couldn’t get an answer on my booking until Expedia themselves contacted me about changing the days we were staying. While the location was great, convenient and good for the price for country calling, the lack of communication was just shocking. As someone who travels often this customer service really needs to improve or I think sales will really suffer.

Reviewed on Oct 5, 2025

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $850, price is now $740 per person
$740
per person
Feb 20 - Feb 23
found 11 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Salisbury (SBY)
8.8/10 Excellent! (1,000 reviews)
Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience.

Reviewed on Dec 5, 2025

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,117, price is now $972 per person
$972
per person
Feb 20 - Feb 23
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!

Reviewed on Aug 23, 2025

Home2 Suites By Hilton Salisbury Fruitland

Home2 Suites By Hilton Salisbury Fruitland

3 out of 5
Price was $791, price is now $700 per person
$700
per person
Feb 20 - Feb 23
found 11 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Salisbury (SBY)
No reviews
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Sherwood Hotel Deals

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
$76 nightly
The price is $87 total per night from Dec 28 to Dec 29
$87 total
Dec 28 - Dec 29
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Great place!

Reviewed on Dec 3, 2025

DoubleTree by Hilton Hotel Annapolis
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
$164 nightly
The price is $187 total per night from Dec 16 to Dec 17
$187 total
Dec 16 - Dec 17
Total with taxes and fees
8.8/10 Excellent! (1,898 reviews)
Rooms are in the different buildings so we needed to check in to find out where we were staying. Parking is difficult so we chose to pay for valet. Loved the location and it was convenient for Midnight Madness shopping and to great restaurants.

Reviewed on Dec 6, 2025

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
$97 nightly
The price is $111 total per night from Dec 15 to Dec 16
$111 total
Dec 15 - Dec 16
Total with taxes and fees
8.6/10 Excellent! (1,017 reviews)
Mold on the fruit at Breakfast. Grapefruit dried out. Broken bathroom fixtures (toilet paper holder & magnifying mirror). No extra blanket in closet since husband and I like to sleep at different temperature. Moldy grout in bathroom.

Reviewed on Dec 2, 2025

Crowne Plaza Annapolis by IHG
See all 1,155 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 $599 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.