Sherwood Vacations

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Find the Best Sherwood Vacation Packages

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 AED 531 per night from Apr 20 to Apr 21
AED 531
AED 730 total
includes taxes & fees
20 Apr - 21 Apr
8.8/10 Excellent! (1,740 reviews)
"Wonderful hotel. Great Staff. The location is optimal to exploring downtown Annapolis. Excellent restaurants within walking distance. Only thing was the room was cold and it was hard to set the room temperature. But the linen bed were comfortable and the room was clean. Would recommend staying ..."

Reviewed on 11 April 2025

Historic Inns of Annapolis
The Westin Annapolis
The Westin Annapolis
4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AED 547 per night from Apr 16 to Apr 17
AED 547
AED 624 total
includes taxes & fees
16 Apr - 17 Apr
8.6/10 Excellent! (1,000 reviews)
"Stayed here for a wedding, but it was our first time to the area. Hotel is great, clean friendly. But the real value was the location. Walking distance to restaurants, convenience, stores, and bars. It was an eight minute walk to a super cute coffee shop, bakery. Parking seemed unnecessarily expensive, ..."

Reviewed on 7 April 2025

The Westin Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4 out of 5
80 Compromise St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AED 702 per night from Apr 20 to Apr 21
AED 702
AED 801 total
includes taxes & fees
20 Apr - 21 Apr
8.8/10 Excellent! (808 reviews)
"Good"

Reviewed on 23 March 2025

Annapolis Waterfront Hotel, Autograph Collection
See all 1,141 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 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.