Sherwood Vacations from $560

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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.
The Inn at Lewes

The Inn at Lewes

3 out of 5
Price was $675, price is now $560 per person
$560
per person
Jun 25 - Jun 28
found 6 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Salisbury (SBY)
6.2/10 (96 reviews)
The staff was very helpful.The gentleman even helped me get into My room and I really appreciate that

Reviewed on Jun 26, 2025

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
Price was $1,892, price is now $1,282 per person
$1,282
per person
Jun 4 - Jun 11
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
9.4/10 Exceptional! (734 reviews)
We have stayed here five or six times in the last few months while doing a beach house renovation, always clean and inviting,the rooms are large and everyone is friendly and helpful.

Reviewed on Apr 9, 2026

Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Save 100% on your flight
Price was $1,135, price is now $840 per person
$840
per person
Jun 4 - Jun 11
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.8/10 Excellent! (1,002 reviews)
Location is perfect. It’s an older hotel set for the beach. Parking is convenient and restaurants and the beach are within a block.

Reviewed on Apr 13, 2026

Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Downtown Bethany Beach
Save 100% on your flight
Price was $2,392, price is now $1,825 per person
$1,825
per person
Jun 4 - Jun 11
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (800 reviews)
Family friendly, peaceful, board walk

Reviewed on Apr 11, 2026

Home2 Suites by Hilton Lewes Rehoboth Beach

Home2 Suites by Hilton Lewes Rehoboth Beach

3 out of 5
Save 100% on your flight
Price was $1,403, price is now $1,145 per person
$1,145
per person
Jun 4 - Jun 11
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
9.4/10 Exceptional! (1,005 reviews)
The front desk staff were extremely helpful. More so than at other hotels. The breakfast was very nice. And the owner, Nicola, actually walked around the breakfast room one day to see how everyone was doing. We would definitely stay there again.

Reviewed on Apr 14, 2026

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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
9.4/10 Exceptional! (379 reviews)
A working marina with nice views from third floor rooms. Smallish rooms with no king beds available, but charming, clean, and with convenient amenities (mini-fridge, microwave, and more traditional coffee maker). Waterside dining available in season and on weekends year-round.

Reviewed on Apr 8, 2026

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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
$178 nightly
The price is $203 total per night from May 10 to May 11
$203 total
May 10 - May 11
Total with taxes and fees
9.4/10 Exceptional! (1,010 reviews)
Outstanding

Reviewed on Apr 11, 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
$199 nightly
The price is $227 total per night from Apr 19 to Apr 20
$227 total
Apr 19 - Apr 20
Total with taxes and fees
9/10 Wonderful! (1,878 reviews)
The room was very small. The elevator was not working. I am too old to be hauling bags up the stairs. Parking was $50 and Historical fee was another $53 dollars so it was more expensive that necessary. I would not stay there again.

Reviewed on Apr 14, 2026

Historic Inns of Annapolis
See all 1,154 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 $560 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.