Title: Sherwood Vacation Packages 2026 from $1,131 | 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 $1,131

## 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.

![Miramar Condominiums](https://images.trvl-media.com/lodging/91000000/90310000/90308700/90308605/f837bfd4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Miramar Condominiums

Downtown Ocean City

$1,131

per person

Mar 23 - Mar 27

found 23 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

9.4/10 Exceptional! (15 reviews)

Stayed in unit 505 and it was beautiful! We loved it!

Reviewed on Aug 23, 2025

![Beach Walk](https://images.trvl-media.com/lodging/91000000/90730000/90727900/90727853/f6dfd7c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Beach Walk

Downtown Ocean City

Save 100% on your flight

$1,975

per person

Mar 23 - Mar 27

found 23 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

7.6/10 Good! (95 reviews)

Everything was exactly what you would expect for a budget friendly room, only complaint was that the steps and porch going to 3rd floor was sketchy and theres a large soft spot on 3rd floor side landing

Reviewed on Oct 17, 2025

![Surf Villa Apartments](https://images.trvl-media.com/lodging/91000000/90620000/90612400/90612343/5e121fab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Surf Villa Apartments

Midtown Ocean City

Save 100% on your flight

$2,094

per person

Mar 23 - Mar 27

found 23 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

9.4/10 Exceptional! (3 reviews)

![Americana Motor Inn](https://images.trvl-media.com/lodging/19000000/18140000/18132800/18132755/4e1c1d86_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Americana Motor Inn

Downtown Ocean City

Save 100% on your flight

$2,195

per person

Mar 23 - Mar 27

found 23 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

8.4/10 Very Good! (883 reviews)

Rooms were clean, best location and very reasonable price.

Reviewed on Oct 22, 2025

![Kings Arms Motel](https://images.trvl-media.com/lodging/6000000/5790000/5789500/5789481/067b70f7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kings Arms Motel

Downtown Ocean City

$1,534

per person

Mar 23 - Mar 27

found 23 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

7.6/10 Good! (220 reviews)

The staff was so helpful and made sure we had plenty of towels. They even let us check in early since we arrived in town before our checkout time. Great location, and very clean.

Reviewed on Oct 6, 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/2026-03-15/2026-03-22/?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

$90 nightly

$99 total

Feb 16 - Feb 17

Total with taxes and fees

9.4/10 Exceptional! (367 reviews)

Always a great time.

Reviewed on Jan 29, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F16%2F2026&endDate=2%2F17%2F2026&selected=9323601&PinnedHotelID=9323601&HadPinnedHotel=true&regionId=6034722)

![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Sonesta ES Suites Annapolis

170 Admiral Cochrane Dr Edgewater MD

Fully refundableReserve now, pay when you stay

$87 nightly

$100 total

Feb 24 - Feb 25

Total with taxes and fees

8.8/10 Excellent! (985 reviews)

We were happy to stay at this place. Very beautiful, warm, comfortable ❤️❤️❤️

Reviewed on Feb 3, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F24%2F2026&endDate=2%2F25%2F2026&selected=2982&PinnedHotelID=2982&HadPinnedHotel=true&regionId=6034722)

![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Graduate by Hilton Annapolis

126 West St Annapolis MD

Fully refundableReserve now, pay when you stay

$161 nightly

$183 total

Feb 22 - Feb 23

Total with taxes and fees

9.2/10 Wonderful! (1,006 reviews)

Clean comfortable room!

Reviewed on Feb 8, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=846&PinnedHotelID=846&HadPinnedHotel=true&regionId=6034722)

[See all 1,158 properties in Sherwood](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F16%2F2026&endDate=2%2F17%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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- [Golf Hotels in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-Golf-Hotel.0-0-d5940-tGolfHotel.Travel-Guide-Filter-Hotels)
- [Family Hotels in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-Family-Hotel.0-0-d5940-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in St. Michaels ](https://www.expedia.com/5Star-St-Michaels-Hotels.s50-0-d5940.Travel-Guide-Filter-Hotels)
- [Gay friendly Hotels in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-LGBT-Welcoming-Hotel.0-0-d5940-tLGBTWelcomingHotel.Travel-Guide-Filter-Hotels)
- [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)
- [Honeymoon Resorts & in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-Honeymoon-Hotels.0-0-d5940-tHoneymoonHotels.Travel-Guide-Filter-Hotels)
- [Casino Hotels in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-Casino-Hotel.0-0-d5940-tCasinoHotel.Travel-Guide-Filter-Hotels)
- [Historic Hotels in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-Historic-Hotel.0-0-d5940-tHistoricHotel.Travel-Guide-Filter-Hotels)
- [Hilton Hotels in St. Michaels ](https://www.expedia.com/St-Michaels-Hotels-Hilton-Hotels.0-0-d5940--bHiltonHotels.Travel-Guide-Filter-Hotels)
- [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)
- [Flights from 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.