Sherwood Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Sherwood
Knapps Narrows Marina & Inn
6176 Tilghman Island Road Sherwood MD
Fully refundableReserve now, pay when you stay
S$211
19 Aug - 20 Aug
includes taxes & fees
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
S$142
30 Aug - 31 Aug
includes taxes & fees
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
S$178
23 Aug - 24 Aug
includes taxes & fees
9/10 Wonderful! (1,936 reviews)
"ac worked fine"
Reviewed on 14 Aug, 2026
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.
Stay near popular Sherwood attractions
Back Creek Community Park
Back Creek Community Park is just one of the places to see in Sherwood, so why not enjoy the other things to explore during your travels? Wander the marina or discover the area's sunsets.
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.
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?
- Pick your dates: The things you want to do in Sherwood and your favourite season will help you decide when to go.
- 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.
- 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.
- Combine your accommodation and airfare: Once you've nailed down your trip dates and duration, book the right Sherwood holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
