Title: Sherwood Vacation Packages 2026 from $248 | Expedia.com

[Sherwood Travel Guide](https://expedia.com/Sherwood.dx6034722)[Hotels in Sherwood](https://expedia.com/Sherwood-Hotels.d6034722.Travel-Guide-Hotels)[Vacation Rentals in Sherwood](https://expedia.com/Sherwood-Vacation-Rentals.d6034722.Travel-Guide-VacationRentals)[Flights to Sherwood](https://expedia.com/Cheap-Flights-To-Sherwood.d6034722.Travel-Guide-Flights)[Car Rentals in Sherwood](https://expedia.com/Car-Rentals-In-Sherwood.d6034722.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6034722/0bcbb682-8042-4738-8664-a432e128f170.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Sherwood Vacations from $248

## Book a Hotel + Flight or Car together to unlock savings

## Your Sherwood Vacation

When you organize a vacation 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 neighborhood 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](https://www.expedia.com/St-Michaels-Winery-St-Michaels.d553248633992438808.Vacation-Attraction), [Chesapeake Bay Maritime Museum](https://www.expedia.com/Chesapeake-Bay-Maritime-Museum-St-Michaels.d553248633992441010.Vacation-Attraction) and [Tilghman Watermen’s Museum](https://www.expedia.com/Tilghman-Watermens-Museum-Tilghman.d553248621555566156.Vacation-Attraction). Whoever you're escaping with and whatever your bank balance, your dream Sherwood vacation is only clicks away with Expedia.

## The Latest Sherwood vacation packages

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

![The Inn at Lewes](https://images.trvl-media.com/lodging/10000000/9110000/9109000/9108984/6fceeb00_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Inn at Lewes

$248

per person

Apr 2 - Apr 4

found 1 day ago

Roundtrip flight included

New York (NYC) to Salisbury (SBY)

6.2/10 (96 reviews)

The staff was very helpful.The gentleman even helped me get into My room and I really appreciate that

Reviewed on Jun 26, 2025

![Bethany Beach Ocean Suites Residence Inn by Marriott](https://images.trvl-media.com/lodging/11000000/10920000/10912400/10912388/f4da198d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bethany Beach Ocean Suites Residence Inn by Marriott

Downtown Bethany Beach

$405

per person

Apr 2 - Apr 4

found 1 day ago

Roundtrip flight included

New York (NYC) to Salisbury (SBY)

9/10 Wonderful! (770 reviews)

excellent room, ocean view....spotless!

Reviewed on Feb 19, 2026

![Club Ocean Villas II](https://images.trvl-media.com/lodging/63000000/62980000/62974900/62974891/a8f648b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Club Ocean Villas II

North Ocean City

$1,000

per person

Apr 17 - Apr 23

found 9 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

8.6/10 Excellent! (58 reviews)

Did not like the outdated furniture, small televisions and the hot tub wasn’t sanitized until the next day. Notified office told them hot tub cover was not on and they said they were waiting for a new cover to come in. Pools don’t open until 10 There were ants on the counter tops and the first night we were locked out . Staff said they had us listed as checked out . We did get new cards immediately. We have stayed in the condos for over 30 years Disappointed especially for paying g what we paid

Reviewed on Jul 7, 2025

![OCHG VIRGINIA LEE](https://images.trvl-media.com/lodging/105000000/104540000/104533500/104533493/b2b89d86_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### OCHG VIRGINIA LEE

Downtown Ocean City

$856

per person

Apr 17 - Apr 23

found 9 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

8.4/10 Very Good! (7 reviews)

We absolutely loved our stay at the OCHG Virginia Lee! We stayed in the top unit and it was amazing! The property manager, Cindy, is top notch and super quick with communication! Highly recommended!

Reviewed on Aug 3, 2025

Don't see what you're looking for?

See all available trips from Columbus to Sherwood

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-23/2026-03-30/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ESN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_6034722)

## Sherwood Hotel Deals

![Knapps Narrows Marina & Inn](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/6fde5623_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Knapps Narrows Marina & Inn

6176 Tilghman Island Road Tilghman MD

Fully refundableReserve now, pay when you stay

$100 nightly

$110 total

Feb 24 - Feb 25

Total with taxes and fees

9.4/10 Exceptional! (370 reviews)

Great!

Reviewed on Feb 19, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F24%2F2026&endDate=2%2F25%2F2026&selected=9323601&PinnedHotelID=9323601&HadPinnedHotel=true&regionId=6034722)

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Historic Inns of Annapolis

58 State Circle Annapolis MD

Fully refundableReserve now, pay when you stay

$208 nightly

$237 total

Mar 1 - Mar 2

Total with taxes and fees

9/10 Wonderful! (1,889 reviews)

Perfect location. Clean room, nice amount of space, and friendly staff.

Reviewed on Feb 19, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true&regionId=6034722)

![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

Fully refundableReserve now, pay when you stay

$83 nightly

$94 total

Mar 8 - Mar 9

Total with taxes and fees

8.6/10 Excellent! (1,005 reviews)

Staff was very friendly and super accommodating.

Reviewed on Feb 22, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=3040&PinnedHotelID=3040&HadPinnedHotel=true&regionId=6034722)

[See all 1,164 properties in Sherwood](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F24%2F2026&endDate=2%2F25%2F2026&regionId=6034722)

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.

## Find the Best Sherwood Vacation Packages

## Sherwood Essential Information

| Language        | English                                                                                                                                                                                                                                                                                                                                                                                  |
| --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
| Currency        | U.S dollars                                                                                                                                                                                                                                                                                                                                                                              |
| Max Temp Winter | 45ºF                                                                                                                                                                                                                                                                                                                                                                                     |
| Max Temp Summer | 80ºF                                                                                                                                                                                                                                                                                                                                                                                     |
| Top Sights      | [St. Michaels Winery](https://www.expedia.com/St-Michaels-Winery-St-Michaels.d553248633992438808.Vacation-Attraction), [Bayside History Museum](https://www.expedia.com/Bayside-History-Museum-North-Beach.d553248621554160436.Vacation-Attraction) and [Tilghman Watermen’s Museum](https://www.expedia.com/Tilghman-Watermens-Museum-Tilghman.d553248621555566156.Vacation-Attraction) |

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## Frequently asked questions

### How much does a Sherwood vacation package cost?

### What are the cheapest months to go to Sherwood?

### How many days is enough for Sherwood?

### How to find the best Sherwood package deals?

### Is it cheaper to book a Sherwood vacation as a package?

### When to book a vacation package to Sherwood?

### Does Expedia offer Book Now, Pay Later Sherwood vacation packages?

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- [5 Star Hotels in St. Michaels ](https://www.expedia.com/5Star-St-Michaels-Hotels.s50-0-d5940.Travel-Guide-Filter-Hotels)
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- [Resorts in St. Michaels ](https://www.expedia.com/St-Michaels-Resorts.d5940-aaResorts.Travel-Guide-Accommodation)
- [Wyndham Hotels in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-Wyndham-Hotels.0-0-d5940--bWyndhamHotels.Travel-Guide-Filter-Hotels)
- [Beach Hotels in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-Beach-Hotel.0-0-d5940-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Hotel Wedding Venues Hotels in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-Wedding-Hotels.0-0-d5940-tWeddingHotels.Travel-Guide-Filter-Hotels)
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- [Casino Hotels in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-Casino-Hotel.0-0-d5940-tCasinoHotel.Travel-Guide-Filter-Hotels)
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- [Hotels with an Outdoor Pool in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-Hotels-With-Outdoor-Pool.0-0-d5940-tHotelswithOutdoorPool.Travel-Guide-Filter-Hotels)

- [Flights from Wittman ](https://www.expedia.com/lp/flights/3000440946/flights-from-wittman)
- [Flights to Bozman ](https://www.expedia.com/Cheap-Flights-To-Bozman.d3000440434.Travel-Guide-Flights)
- [Flights from Bozman ](https://www.expedia.com/lp/flights/3000440434/flights-from-bozman)
- [Flights from Neavitt ](https://www.expedia.com/lp/flights/3000347944/flights-from-neavitt)
- [Flights to Tilghman ](https://www.expedia.com/Cheap-Flights-To-Tilghman.d166219.Travel-Guide-Flights)
- [Chicago to Tilghman ](https://www.expedia.com/lp/flights/178248/166219/chicago-to-tilghman)
- [Flights to McDaniel ](https://www.expedia.com/Cheap-Flights-To-McDaniel.d6343444.Travel-Guide-Flights)
- [Flights to St. Michaels ](https://www.expedia.com/Cheap-Flights-To-St-Michaels.d5940.Travel-Guide-Flights)

- [Visit Wittman ](https://www.expedia.com/Wittman.dx3000440946)
- [Visit Bozman ](https://www.expedia.com/Bozman.dx3000440434)
- [Phillips Wharf Environmental Center ](https://www.expedia.com/Phillips-Wharf-Environmental-Center-Tilghman.d553248621532662262.Vacation-Attraction)
- [Visit Neavitt ](https://www.expedia.com/Neavitt.dx3000347944)
- [Tilghman Vacations ](https://www.expedia.com/Tilghman.d166219.Destination-Travel-Guides)
- [Visit Tilghman ](https://www.expedia.com/Tilghman.dx166219)
- [Visit McDaniel ](https://www.expedia.com/McDaniel.dx6343444)
- [St. Michaels Vacations ](https://www.expedia.com/St-Michaels.d5940.Destination-Travel-Guides)
- [St. Michaels Winery ](https://www.expedia.com/St-Michaels-Winery-St-Michaels.d553248633992438808.Vacation-Attraction)
- [St. Michaels Museum ](https://www.expedia.com/St-Michaels-Museum-St-Michaels.d553248621561196327.Vacation-Attraction)
- [Chesapeake Bay Maritime Museum ](https://www.expedia.com/Chesapeake-Bay-Maritime-Museum-St-Michaels.d553248633992441010.Vacation-Attraction)
- [Claiborne Vacations ](https://www.expedia.com/Claiborne.d3000440483.Destination-Travel-Guides)
- [Visit St. Michaels ](https://www.expedia.com/St-Michaels.dx5940)

- [Car rentals near Wittman ](https://www.expedia.com/Car-Rentals-In-Wittman.d3000440946.Car-Rental-Guide)
- [Car rentals near Bozman ](https://www.expedia.com/Car-Rentals-In-Bozman.d3000440434.Car-Rental-Guide)
- [Car rentals near Tilghman ](https://www.expedia.com/Car-Rentals-In-Tilghman.d166219.Car-Rental-Guide)
- [Island Car Rentals Rental Cars in Tilghman ](https://www.expedia.com/Island-Car-Rentals-Car-Rentals-In-Tilghman.d166219-c1132.Car-Rental-Guide-Suppliers)
- [Car rentals near McDaniel ](https://www.expedia.com/Car-Rentals-In-McDaniel.d6343444.Car-Rental-Guide)
- [Car rentals near St. Michaels ](https://www.expedia.com/Car-Rentals-In-St-Michaels.d5940.Car-Rental-Guide)
- [Enterprise Rental Cars in St. Michaels ](https://www.expedia.com/Enterprise-Car-Rentals-In-St-Michaels.d5940-c15.Car-Rental-Guide-Suppliers)

- [Bozman Vacation Rentals ](https://www.expedia.com/Bozman-Vacation-Rentals.d3000440434.Travel-Guide-VacationRentals)
- [Neavitt Vacation Rentals ](https://www.expedia.com/Neavitt-Vacation-Rentals.d3000347944.Travel-Guide-VacationRentals)
- [Tilghman Vacation Rentals ](https://www.expedia.com/Tilghman-Vacation-Rentals.d166219.Travel-Guide-VacationRentals)
- [St. Michaels Vacation Rentals ](https://www.expedia.com/St-Michaels-Vacation-Rentals.d5940.Travel-Guide-VacationRentals)

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