Sherwood Vacation Packages

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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.

Top Sherwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was CA $1,269, price is now CA $1,152 per person
CA $1,152
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
7.4/10 Good! (179 reviews)

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was CA $3,973, price is now CA $3,269 per person
CA $3,269
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
7.6/10 Good! (128 reviews)
We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel.

Reviewed on Oct 13, 2026

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was CA $2,306, price is now CA $2,082 per person
CA $2,082
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
9.4/10 Exceptional! (34 reviews)

Cypress River Inn & Spa

Cypress River Inn & Spa

5 out of 5
Price was CA $2,444, price is now CA $2,220 per person
CA $2,220
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.4/10 Very good! (7 reviews)

Club Ocean Villas II by Coolvacay

Club Ocean Villas II by Coolvacay

3.5 out of 5
North Ocean City
Price was CA $1,843, price is now CA $1,693 per person
CA $1,693
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.4/10 Very good! (74 reviews)
La casa lucia limpia y todo, pero muchas las luces de las habitaciones y de la casa no funcionaban, a parte la tina de hidromasaje

Reviewed on Sep 22, 2026

Ready to book your vacation to Sherwood?

 

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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
The price is CA $168 per night from Nov 30 to Dec 1
CA $168
CA $185 total
Nov 30 - Dec 1
includes taxes & fees
9.4/10 Exceptional! (401 reviews)
"We are boaters so love the atmosphere of staying in a marina with a boat yard. The sunsets were beautiful there. Make sure you get a room facing the bay."

Reviewed on Oct 23, 2026

Knapps Narrows Marina & Inn
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
The price is CA $139 per night from Nov 30 to Dec 1
CA $139
CA $206 total
Nov 30 - Dec 1
includes taxes & fees
Historic Inns of Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Nov 30 to Dec 1
CA $176
CA $242 total
Nov 30 - Dec 1
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"As far as I'm concerned one of the best places to stay in the area"

Reviewed on Oct 30, 2026

Rod 'N' Reel Resort
See all 1,164 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.
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Stay near popular Sherwood attractions

Goat Island

Commune with nature and explore the great outdoors at Goat Island during your travels in Sherwood. Wander the marina or discover the area's sunsets.
See properties

Frequently asked questions

How much does a Sherwood vacation package cost?
You'll find cheap prices from CA $1,152 on Expedia for your Sherwood getaway. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Sherwood costs.
What are the cheapest months to go to Sherwood?
Plan your trip for the shoulder or low season and you're likely to get cheap Sherwood vacation packages. Keep in mind that school vacation periods and major local events can impact prices, so do some research before booking.
How many days is enough for Sherwood?
Typically, a handful of days is enough to see the top sights during your Sherwood vacation. But if you prefer to have some time to chill out or take day trips, consider extending your itinerary.
How to find the best Sherwood package deals?
Start your search for a Sherwood package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Sherwood package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Sherwood escape off to a flying start.
Is it cheaper to book a Sherwood vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still have the flexibility to create a customized Sherwood vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Sherwood?
Secure incredible discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Sherwood getaway.
How to plan a trip to Sherwood?

  1. Choose when to travel: Check your calendar and get your bags packed. Your favourite time of year and the activities on offer will also help you decide when to visit Sherwood.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Sherwood.
  3. Work out your trip length: Consider how long you'd like to spend discovering Sherwood. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Sherwood vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.