Sherwood Holidays

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Top hotels in Sherwood

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
8.8/10 Excellent! (1,775 reviews)
"Great location near the dock!"

Reviewed on 14 Jun, 2025

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Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
The price is S$160 per night from 13 Jul to 14 Jul
S$160
13 Jul - 14 Jul
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"Hotel was clean, staff was friendly. Within walking distance of shops, restaurant and landmarks."

Reviewed on 14 Jun, 2025

Hilton Garden Inn Annapolis Downtown
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 S$226 per night from 13 Jul to 14 Jul
S$226
13 Jul - 14 Jul
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"We had a great stay. Walkable to everything we wanted to do. Quaint little town."

Reviewed on 12 Jun, 2025

Graduate by Hilton Annapolis
See all 1,177 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.

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.

* 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.