Sherwood Trips (flight + hotel)

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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! (1,817 reviews)
Sail and lighthouse trip
"Perfect location easy access to shops, restaurants, and City Dock. Confortable beds and a lot of connections for devices. Be careful in shower, VERY slippery. Ask front desk for shower mat, but they never delivered."

Reviewed on Aug 3, 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 P9,014 per night from Aug 10 to Aug 11
P9,014
P10,276 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
First class
"It was pouring when we arrived, my wife and i were soaked and the staff was at the front desk with warm towels. Beginning to end first class service, attentiveness and respectful."

Reviewed on Jul 28, 2025

Graduate by Hilton Annapolis
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 P5,835 per night from Aug 10 to Aug 11
P5,835
P6,652 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
7 out of 10 stars
"The hotel is older and as we walked through we were saying how it could be (& you can tell it was) a really nice hotel. Don’t misunderstand, it was a nice hotel, but you can tell it’s ‘used’. There are scuffs on doors and walls, there are tiles broken on floors, etc. the room itself was clean. The ..."

Reviewed on Jul 27, 2025

DoubleTree by Hilton Hotel Annapolis
See all 1,186 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 vacation package cost?
You can snap up a vacation package to this destination on Expedia. However, how much your vacation 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 vacation 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 vacation. 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 customize 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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Sherwood vacation as a package?
You can enjoy significant savings on your Sherwood break by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Sherwood?
If you have your Sherwood vacation 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 favorite 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 accommodations and airfare: Once you've nailed down your trip dates and duration, book the right Sherwood vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.