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.
Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
North Ocean City
per person
Oct 8 - Oct 12
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
8.2/10 Very Good! (1,410 reviews)
The wait for the elevator could get backed up… and layout in the lobby could be better, very congested especially during check in

Reviewed on Aug. 5, 2025

The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
per person
Oct 24 - Oct 27
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
9.8/10 Exceptional! (263 reviews)
I am so glad I chose Surf Shanty to stay at! The man at the front desk was so nice and helpful upon checking in. The location was perfect! Less than a block to the beach, on the quieter end of the strip but still walkable to everything. The room was clean and you can tell they put thought into this hotel. All the colors and decor are cohesive and beachy. There is an outdoor shower to rinse the sand off before going back to your room. The beds are super comfortable. We will definitely be back!

Reviewed on Aug. 5, 2025

Comfort Inn & Suites Milford

Comfort Inn & Suites Milford

2.5 out of 5
per person
Oct 24 - Oct 27
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
8/10 Very Good! (575 reviews)
If details matter, you won’t like this hotel. My sink faucet was leaking. My tub faucet was dripping. Tub base was stained. Otherwise my stay was fine. Nice people at the desk.

Reviewed on Jul. 9, 2025

Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
per person
Oct 24 - Oct 27
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
8.6/10 Excellent! (1,000 reviews)
Noisy at night but expected. No food but a vendimg machine was available Nice and clesn room .

Reviewed on Aug. 5, 2025

The Marylander Condo & Hotel

The Marylander Condo & Hotel

4 out of 5
North Ocean City
per person
Oct 8 - Oct 12
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
8/10 Very Good! (38 reviews)
As great location and close to the beach access.

Reviewed on Aug. 12, 2024

Ready to book your vacation to Sherwood?

 

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Sherwood Hotel Deals

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 $140 per night from Aug 12 to Aug 13
CA $140
CA $207 total
Aug 12 - Aug 13
includes taxes & fees
8.8/10 Excellent! (1,820 reviews)
"Hotel was very quaint, valet is a little steep at 50 dollars a day so I would recommend off street parking."

Reviewed on Aug. 4, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Aug 17 to Aug 18
CA $213
CA $243 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Charming spot close to everything with excellent amenities and service."

Reviewed on Aug. 4, 2025

Graduate by Hilton Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Aug 17 to Aug 18
CA $147
CA $167 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (848 reviews)
"Great room for a great price... Very friendly staff, too."

Reviewed on Jul. 17, 2025

Sonesta ES Suites Annapolis
See all 1,184 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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Frequently asked questions

How much does a Sherwood vacation package cost?
You'll find cheap prices from CA $715 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.