Sherwood Holidays

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Your Sherwood Holiday

When you organise a holiday 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 neighbourhood 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 holiday is only clicks away with Expedia.

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

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! (1,817 reviews)
"Liked the historic feel and the archeological dig site located just off the lobby (and still inside the hotel)! Tahina gave excellent customer support"

Reviewed on 8 Aug 2025

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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 £132 per night from 17 Aug to 18 Aug
£132
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"This hotel is great. Good location accommodations are beautiful. The only thing they lack is a coffee maker in the room."

Reviewed on 7 Aug 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 £80 per night from 10 Sept to 11 Sept
£80
10 Sept - 11 Sept
includes taxes & fees
8.8/10 Excellent! (851 reviews)
"Great room for a great price... Very friendly staff, too."

Reviewed on 17 Jul 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
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Family Friendly Holidays

Frequently asked questions

Why should I book my Sherwood holiday with Expedia?
With great-value airfares, car hire and accommodation options all in the same place, Expedia makes arranging your Sherwood getaway hassle-free. Moreover, we can help you bundle your bookings into a package holiday so you can enjoy even more savings. Pick from amazing properties, add flights and/or a car hire (and maybe even some fun activities!) and land incredible prices. Need to cancel? Expedia offers a flexible cancellation policy for many reservations. To learn more, check out our Customer Service Portal link.
When is the best time of year to holiday in Sherwood?
Peak season falls in May, June and July and is an exciting time to visit — if you don't mind the crowds. November, December and January are usually quieter times of the year. To get an idea of what type of weather to expect, the average daytime temperature in January, the coolest time of year in Sherwood, is 2ºC. The warmest period here is July, when temperatures are around 25ºC.
What is the top hotel for my holiday in Sherwood?
Create unforgettable memories in Sherwood by choosing Courtyard by Marriott Baltimore Downtown/McHenry Row as your home-away-from-home and gateway to adventure and fun.
How do I get a cheap holiday to Sherwood?
If you love bargains, combine your bookings into a Sherwood holiday. Whether you're chasing hotels, flights, hire cars or day tours, you can browse and book everything in one place. You'll have loads of choice at your fingertips too. Expedia has more than 400 partner airlines and 321,000 hotels all over the world to take your pick of. Fly with who you want, stay in a place you like and save a tidy sum — now that's the perfect getaway! Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Sherwood holiday?
There's an almost endless list of places to check out while enjoying a holiday in Sherwood. St. Michaels Winery, Chesapeake Bay Maritime Museum, St. Michaels Museum and Tilghman Watermen's Museum are among this destination's top attractions.
Do I need a visa for my Sherwood holiday?
Check the most up-to-date information on official government websites. Your nationality and whether you're visiting for study, leisure or business will determine if you require a visa for Sherwood. Make yourself familiar with the application process, including any required documentation, fees and turnaround times. Finalise your application well in advance to allow plenty of time for processing. Some visas may take several weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Sherwood holiday?
Though everyone's fashion style varies, it can be helpful to have some guidelines for what to bring during your holiday in Sherwood. We recommend searching style blogs before you go to get inspiration for local fashion trends. Pack your bags with confidence by looking up the local weather conditions in Sherwood. July brings the warmest temperatures, with daytime averages of 25ºC, while January days average 2ºC, making it the coolest time of year.
What does an Expedia Sherwood holiday include?
It all depends on what sort of trip you're thinking about. Sherwood travel deals can include car hires, hotels and flights. You can mix and match to create the bundle that suits you. You can also add on activities and experiences after you've booked to land even bigger discounts. Private holiday homes and cottages are a couple of the most popular property types in Sherwood. Whatever your preference or size of your group, you can count on Expedia for the freedom to personalise your next big adventure.
Does Expedia offer Book Now, Pay Later Sherwood holidays?
We sure do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in instalments. Simply click on the payment plan that works for you during checkout and take the stress out of budgeting for your trip. Be sure to bundle your accommodation, flights and activities with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that suit all types of budgets, so you can lock in that well-deserved holiday sooner.
  • No-deposit holidays: When you come across an awesome deal but your budget doesn't quite cover it yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to secure your getaway.

Can I choose my airline with a Sherwood Expedia holiday?
Yes, you sure can. We have more than 400 airline partners across the globe, so select the carrier that's a good fit for your travel preferences.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.