Sherwood Vacations from $768

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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.
Empress Motel

Empress Motel

2 out of 5
Downtown Ocean City
Price was $982, price is now $768 per person
$768
per person
Jun 7 - Jun 12
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
7.8/10 Good! (149 reviews)
Exactly as advertised and a 2 minute walk to the beach. Would stay again.

Reviewed on Oct 16, 2025

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,934, price is now $1,261 per person
$1,261
per person
Jun 7 - Jun 12
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
8/10 Very Good! (31 reviews)
The unit was outdated, small, and had mismatched and old furniture. The shower in one of our bathrooms wouldn’t drain. The oven did not work. There was only one television. Concerns couldn’t be communicated because the staff hardly spoke English (although they were very nice). The unit was in a really nice location - 1.5 blocks from the boardwalk and beach. We liked the outside showers.

Reviewed on Aug 9, 2025

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $1,425, price is now $1,069 per person
$1,069
per person
May 1 - May 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
8.2/10 Very Good! (699 reviews)
Front desk staff was great!!

Reviewed on Mar 15, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $1,214, price is now $931 per person
$931
per person
May 1 - May 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
9/10 Wonderful! (3,461 reviews)
very clean room, great breakfast.

Reviewed on Mar 27, 2026

Lankford Hotel and Lodge

Lankford Hotel and Lodge

3.5 out of 5
Downtown Ocean City
Price was $1,041, price is now $806 per person
$806
per person
May 1 - May 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
8.6/10 Excellent! (639 reviews)
The staff was very friendly. It was right on the boardwalk with direct beach access. Fully stocked with plates, cups, and utensils. I would recommend this hotel again and again!!!!

Reviewed on Oct 28, 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
$100 nightly
The price is $110 total per night from Mar 29 to Mar 30
$110 total
Mar 29 - Mar 30
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
$173 nightly
The price is $197 total per night from Apr 19 to Apr 20
$197 total
Apr 19 - Apr 20
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
Unique hotel in the heart of Annapolis. The room was lovely, comfortable and well equipped. Parking was a bit expensive $32 one day and strange, couldnt actually park in the covered garrage that was only for vallette patrons. Would have been nice to have a regular coffee maker in the room, only instant ...

Reviewed on Mar 27, 2026

Graduate by Hilton 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
$174 nightly
The price is $198 total per night from Apr 5 to Apr 6
$198 total
Apr 5 - Apr 6
Total with taxes and fees
9/10 Wonderful! (1,863 reviews)
Clean room, friendly staff, and the PERFECT location for walking downtown Annapolis.

Reviewed on Mar 24, 2026

Historic Inns of Annapolis
See all 1,143 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 $768 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.