Sherwood Holidays

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Your Sherwood Holiday

Take the stress out of planning your next epic adventure with a Sherwood holiday package. Whether you've come for its food, history, art or something else, you'll find countless exciting experiences to delve into. Any trip to Sherwood needs a well-crafted itinerary. Fill yours with famous sights like St. Michaels Winery, Chesapeake Bay Maritime Museum and St. Michaels Museum. Whatever your travel plans or budget, putting together a tailored Sherwood holiday is a piece of cake with Expedia.

Sherwood Holiday

Sherwood Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
St. Michaels Winery, Bayside History Museum and Oxford Museum

Our pick of the best 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! (388 reviews)
"Great place!"

Reviewed on 25 June 2026

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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 AU$197 per night from 14 July to 15 July
AU$197
14 July - 15 July
includes taxes & fees
9/10 Wonderful! (1,867 reviews)
"Staff was friendly, helpful and wonderful. Room was good, location is great."

Reviewed on 3 July 2026

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 5 July to 6 July
AU$156
5 July - 6 July
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"The room is clean. Spacious and quiet. Bed is comfortable. We will stay here again."

Reviewed on 3 July 2026

DoubleTree by Hilton Hotel Annapolis
See all 1,172 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.
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Frequently asked questions

How much does a Sherwood holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday to Sherwood costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Sherwood?
To pick up cheap Sherwood holiday packages, plan your getaway outside of busy periods like public holidays and major events. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Sherwood?
Usually, a handful of days is enough to visit the major attractions during your Sherwood holiday. But if you want to have more time to kick back or take day tours, think about extending your itinerary.
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 customise 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Sherwood holiday as a package?
You can enjoy significant savings on your Sherwood break by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Sherwood?
If you have your Sherwood holiday 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.
How to plan a trip to Sherwood?

  1. Pick your dates: The things you want to do in Sherwood and your favourite season will help you decide when to go.
  2. Set your budget: Factor in costs like flights, meals and transportation when calculating how much to put aside for your trip to Sherwood. Then, pick a hotel that matches your budget, whether that's a low-cost option or a more luxurious retreat.
  3. Decide your trip length: Consider how much time you want to spend discovering Sherwood. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your accommodation and airfare: Once you've nailed down your trip dates and duration, book the right Sherwood holiday package for you.

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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.