Sherwood Vacations from $750

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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.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $905, price is now $750 per person
$750
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
7.4/10 Good! (170 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

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $920, price is now $772 per person
$772
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
9/10 Wonderful! (3,316 reviews)
Our room was clean and neat but far from spotless. There were stains on carpet, dirt on bathroom floor in corners. Honestly, all the rooms and entire hotel frankly need updating.

Reviewed on Dec 21, 2025

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,009, price is now $857 per person
$857
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.8/10 Excellent! (1,000 reviews)
The property was marketed as luxury but it's far from it. My headboard was shredded. Bathtub had hair. Heating was inconsistent

Reviewed on Dec 21, 2025

Cypress River Inn & Spa

Cypress River Inn & Spa

5 out of 5
Price was $1,528, price is now $1,317 per person
$1,317
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
No reviews
Salisbury Riverfront Lofts

Salisbury Riverfront Lofts

3 out of 5
Price was $901, price is now $792 per person
$792
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
9.4/10 Exceptional! (23 reviews)
Great spot and well appointed. Great communicator. HVAC loud and might consider brighter bulbs in lamps.

Reviewed on Nov 17, 2024

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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
$75 nightly
The price is $85 total per night from Jan 4 to Jan 5
$85 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (1,021 reviews)
Overall great experience

Reviewed on Dec 23, 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
$169 nightly
The price is $193 total per night from Jan 1 to Jan 2
$193 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.8/10 Excellent! (1,907 reviews)
Best place to stay is the main building

Reviewed on Dec 22, 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
$106 nightly
The price is $121 total per night from Jan 25 to Jan 26
$121 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
Very clean room, breakfast was delicious and parking was safe On thing that bothered me though… I visited the gym three days in a row and all three days there were no wipes for the machines and nothing to clean the machines with. It a post-covid world that is not acceptable.

Reviewed on Dec 17, 2025

Crowne Plaza Annapolis by IHG
See all 1,150 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 $750 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.