Sherwood Vacations from $843

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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 $1,020, price is now $843 per person
$843
per person
May 18 - May 23
found 13 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.2/10 Very Good! (699 reviews)
Please don’t believe these reviews I had an excellent experience. The hotel was older but is a mom and pop hotel family feel.

Reviewed on Mar 31, 2026

Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Downtown Bethany Beach
Price was $1,325, price is now $1,055 per person
$1,055
per person
May 23 - May 25
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (794 reviews)
We had a wonderful stay from start to finish. We were greeted warmly at reception, and checked into an incredibly spacious room with balcony. The hotel is centrally located and it was easy to pop out to walk to the beach or shops, and also to hop in the car and explore further. We enjoyed the spacious indoor/outdoor pool while the roof was partially retracted. We also had the breakfast buffet the next morning, which had more than enough options for both kids and adults. We would definitely stay here again, and regretted making this a shorter trip!

Reviewed on Mar 29, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $1,297, price is now $1,035 per person
$1,035
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
9/10 Wonderful! (3,461 reviews)
I stayed one night there and it’s my third time I reserved this hotel, so clean, big room , bed more comfortable, friendly staff.

Reviewed on Mar 31, 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,256, price is now $1,029 per person
$1,029
per person
May 23 - May 25
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
9.4/10 Exceptional! (725 reviews)
Good stay as always. Thank you

Reviewed on Mar 29, 2026

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $1,640, price is now $1,356 per person
$1,356
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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
$150 nightly
The price is $165 total per night from Apr 7 to Apr 8
$165 total
Apr 7 - Apr 8
Total with taxes and fees
9.4/10 Exceptional! (375 reviews)
A convenient, charming Inn with scenic views and helpful staff. My room was clean, quiet and comfortable. Delicious Continental breakfast included fresh fruit salad and cold cereal in addition to yogurt and baked goods. Looking forward to returning.

Reviewed on Mar 27, 2026

Knapps Narrows Marina & Inn
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $204 total per night from Apr 19 to Apr 20
$204 total
Apr 19 - Apr 20
Total with taxes and fees
9.4/10 Exceptional! (1,005 reviews)
The room was clean and comfortable. The hotel was decorated with a fun nautical theme. The location is excellent and close to dining and shopping.

Reviewed on Mar 31, 2026

Graduate by Hilton Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$174 nightly
The price is $198 total per night from Apr 19 to Apr 20
$198 total
Apr 19 - Apr 20
Total with taxes and fees
9/10 Wonderful! (1,871 reviews)
The parking valet was wonderful- so easy to park and also gave us recommendations of where to eat! Front desk personnel were also lovely.

Reviewed on Apr 1, 2026

Historic Inns of Annapolis
See all 1,146 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 $843 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.