Sherwood Holidays from £859

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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.

The Latest Sherwood Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
per person
15 Sept - 21 Sept
found 1 day ago
Return flight included
London (LON) to Salisbury (SBY)
7.6/10 Good! (57 reviews)
Amazing coffee available at the front desk and crazy cool location

Reviewed on 21 Jun 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
per person
15 Sept - 21 Sept
found 1 day ago
Return flight included
London (LON) to Salisbury (SBY)
9/10 Wonderful! (2,901 reviews)
Very nice clean hotel. Front desk guy was skeevy and the balcony was uncomfortable but other than that very nice!

Reviewed on 22 Jun 2025

Cambria Hotel Ocean City - Bayfront

Cambria Hotel Ocean City - Bayfront

3 out of 5
Downtown Ocean City
per person
15 Sept - 21 Sept
found 1 day ago
Return flight included
London (LON) to Salisbury (SBY)
9.2/10 Wonderful! (1,000 reviews)
Great place to stay for families. Loved the bay view from the balcony and seeing all of the boats pass by daily. Beautiful grounds and areas to hang out and relax.

Reviewed on 20 Jun 2025

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
per person
15 Sept - 21 Sept
found 1 day ago
Return flight included
London (LON) to Salisbury (SBY)
7.2/10 Good! (149 reviews)
The property itself was good, a little dated but clean otherwise. The three women working the desk were the best part. They were very kind and accommodating to my family. The only part that was not so good was the small print from expedia about this being a timeshare property as we had to change rooms mid trip.

Reviewed on 17 Jun 2025

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
per person
15 Sept - 21 Sept
found 1 day ago
Return flight included
London (LON) to Salisbury (SBY)
8.6/10 Excellent! (1,000 reviews)
Well positioned ocean front great staff alot of fun

Reviewed on 24 Jun 2025

Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
North Ocean City
per person
15 Sept - 21 Sept
found 1 day ago
Return flight included
London (LON) to Salisbury (SBY)
8.2/10 Very Good! (1,240 reviews)
This place is not what I expected. I was on the 9th floor.. pool was not clean look like someone vomit inside the pool. The hallways smelt like dogs

Reviewed on 23 Jun 2025

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
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,785 reviews)
"We loved the area as well as the hotel. It's a 4 minute walk from the waterfront and has a great view of the state capital building. My only complaint would be that the A/C for my room stop functioning on my fourth night. We were moved to another room and the A/C in that room also didn't work. They ..."

Reviewed on 20 Jun 2025

Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful ...
8.4/10 Very Good! (1,000 reviews)
"Conveniently located and clean. Great prices"

Reviewed on 19 Jun 2025

Hilton Garden Inn Annapolis Downtown
Best Western Annapolis
Best Western Annapolis
2.5 out of 5
2520 Riva Rd, Annapolis, MD
Stay at this business-friendly hotel in Annapolis. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
7.8/10 Good! (1,006 reviews)
"good"

Reviewed on 22 Jun 2025

Best Western Annapolis
See all 1,176 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

Family Friendly Holidays

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.