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

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$286 per night from 31 Mar to 1 Apr
AU$286
includes taxes & fees
31 Mar - 1 Apr
8.8/10 Excellent! (1,725 reviews)
"Friendly and helpful staff and lovely rooms including foyer and meeting rooms. Individual room could have used a bath mat for floor and grab bars and mat in shower for safety sake. Would definitely stay there again."

Reviewed on 20 Mar. 2025

Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG
3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is AU$176 per night from 15 Apr to 16 Apr
AU$176
includes taxes & fees
15 Apr - 16 Apr
8.6/10 Excellent! (1,000 reviews)
"Stayed for one night here at the Crowne and had a great stay. The room was nice with comfy beds. The hotel was near lots of restaurants and had its own bar restaurant as well. Food was decent. Downtown Annapolis is only about 10 minutes away. Would definitely stay here again when in Annapolis."

Reviewed on 2 Mar. 2025

Crowne Plaza Annapolis by IHG
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$173 per night from 27 Mar to 28 Mar
AU$173
includes taxes & fees
27 Mar - 28 Mar
8.4/10 Very Good! (1,001 reviews)
"Jody was an outstanding guest services Representative!!!"

Reviewed on 18 Mar. 2025

DoubleTree by Hilton Hotel Annapolis
See all 1,139 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

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.