Sherwood Packages (Flight + Hotel)

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Top hotels in Sherwood

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road Sherwood MD
Fully refundableReserve now, pay when you stay
The price is ฿5,007 per night from 9 Aug to 10 Aug
฿5,007
฿5,507 total
9 Aug - 10 Aug
includes taxes & fees
9.4/10 Exceptional! (393 reviews)
"Spacious room with balcony and very friendly staff. Would definitely stay again"

Reviewed on 29 Jul 2026

Knapps Narrows Marina & Inn
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 ฿3,882 per night from 5 Aug to 6 Aug
฿3,882
฿5,569 total
5 Aug - 6 Aug
includes taxes & fees
9/10 Wonderful! (1,904 reviews)
"This is our 2nd visit here and primarily chosen for location, historical significance and cleanliness. Located directly in the hub of beautiful Annapolis, it is easy walking and convenient to all shops, restaurants and the harbor. The rooms are nicely decorated with all the amenities needed for a ..."

Reviewed on 1 Aug 2026

Historic Inns of Annapolis
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
The price is ฿2,979 per night from 23 Aug to 24 Aug
฿2,979
฿3,277 total
23 Aug - 24 Aug
includes taxes & fees
St Michaels Inn
See all 1,168 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.

Stay near popular Sherwood attractions

Goat Island

Commune with nature and explore the great outdoors at Goat Island during your travels in Sherwood. Wander the marina or discover the area's sunsets.
See properties

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.

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