Book Exclusive Sherwood Vacation Packages

Choose one or more items to build your trip:

Sherwood flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Comfort Suites Ocean City West

Comfort Suites Ocean City West

2.5 out of 5
West Ocean City
Price was CA $713, price is now CA $679 per person
CA $679
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Salisbury (SBY)
Book a stay at this family-friendly hotel in Ocean City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ocean City Beach and Ocean City Boardwalk are located nearby.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was CA $725, price is now CA $686 per person
CA $686
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Salisbury (SBY)
Book a stay at this beach hotel in Dewey Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Rehoboth Beach Boardwalk and Rehoboth Beach are located nearby.
Cambridge Inn

Cambridge Inn

2 out of 5
Price was CA $722, price is now CA $686 per person
CA $686
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Salisbury (SBY)
Stay at this hotel in Cambridge. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Bay Country Shop and Dorchester County Historical Society are located nearby.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was CA $719, price is now CA $687 per person
CA $687
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Salisbury (SBY)
Stay at this motel in Pocomoke City. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Newtown Park and Pocomoke Fair Grounds are located nearby.
Motel 6 Pocomoke City, MD

Motel 6 Pocomoke City, MD

2 out of 5
Price was CA $709, price is now CA $680 per person
CA $680
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Salisbury (SBY)
Stay at this hotel in Pocomoke City. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Newtown Park and Pocomoke Fair Grounds are located nearby.

Top Sherwood hotels deals

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road Sherwood MD
The price is CA $210 per night
CA $210
CA $231 total
Sep 20 - Sep 21
includes taxes & fees
Stay at this hotel in Sherwood. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Knapp's Narrows Marina & Inn and Back Creek Community Park are located nearby.
Pool
Breakfast included
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Free cancellation
Reserve now, pay when you stay
The price is CA $116 per night
CA $116
CA $132 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Annapolis City Dock and Annapolis Harbor Center Shopping Center are located nearby.
Pet-friendly
Parking included
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Free cancellation
Reserve now, pay when you stay
The price is CA $138 per night
CA $138
CA $205 total
Oct 12 - Oct 13
includes taxes & fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Annapolis City Dock and Sandy Point State Park are located nearby.
Pet-friendly
Free WiFi
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Free cancellation
The price is CA $154 per night
CA $154
CA $175 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Annapolis City Dock and Westfield Annapolis Mall are located nearby.
Pool
Parking included
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Free cancellation
Reserve now, pay when you stay
The price is CA $208 per night
CA $208
CA $237 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Annapolis City Dock and Sandy Point State Park are located nearby.
Pet-friendly
Free WiFi
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Free cancellation
Reserve now, pay when you stay
The price is CA $198 per night
CA $198
CA $267 total
Oct 7 - Oct 8
includes taxes & fees
Book a stay at this business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chesapeake Beach Railway Museum and Rod n Reel Charter Fishing are located nearby.
Pool
Spa
Don't see what you're looking for?
See all available properties in Sherwood
View all properties
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

Back Creek Community Park

Back Creek Community Park is just one of the places to see in Sherwood, so why not enjoy the other things to explore during your travels? Wander the marina or discover the area's sunsets.
See properties

Sherwood Vacations

Get your journey started on the right foot by knowing a bit about Sherwood before you jet off.

If you travel 12 miles (19 kilometers) southeast of Shady Side, or 12 miles (19 kilometers) east of Chesapeake Beach, you'll be in Sherwood.

Places to visit in Sherwood

Forget your history journals! Allow the past to jump to life at Tilghman Watermen’s Museum. Want some more ideas? Our natural environment is an interconnected and wonderful thing. Phillips Wharf Environmental Center is a good place to go to find out more about it. But there's more. The labels on wine bottles usually only provide us with part of the story about the drop inside. Why not take a tour around St. Michaels Winery to hear the full history behind their blends?

Where do you fly into for Sherwood?

Fasten your seatbelt, stow your tray table and get set to explore Sherwood! Once the wheels hit the tarmac at Baltimore Washington International Thurgood Marshall Airport (BWI), the buzzing main streets will be just 35 miles (56 kilometers) to the southeast from here.

Frequently asked questions

How much are vacation packages to Sherwood?
With vacation packages available for only CA $679, you won't need to drain your bank balance for your getaway to Sherwood. Travelocity can help. Bundle up flights, hotels and experiences into a package and score exciting discounts. The more you book, the bigger the savings.
How long should my Sherwood vacation be?
Most people choose to spend around 2 nights in Sherwood, but it's entirely up to you. If you're hoping to explore all the fantastic things this location has waiting for you, why not hang around for a couple of extra nights?
Where can I get the best vacation package deals for Sherwood?
Travelocity will be able to help you snap up an unbeatable Sherwood package deal. With 400 airlines and 665,000 properties across the globe, you're bound to find the perfect mix.
Why should I purchase my Sherwood vacation package via Travelocity?
Nothing tops the peace of mind knowing you've just picked up the best price around — that's our Price Match Guarantee. Add to that our enormous range of magical destinations and 24/7 team of customer service professionals and you've got the blueprint for a stress-free vacation.
Will I save money on my Sherwood car rental if I combine it with my hotel or flight?
With a Sherwood vacation package, you can combine your car, flight and hotel bookings and save a whole lot. If you're in the mood to see the best of this impressive region, why not make tracks to White House? This well-known attraction is 64 kilometersfrom Sherwood. With your own rental car, you'll be there in no time.
What is the best time of year to go to Sherwood?
Pack your bags in and spend more of your money on experiences, not your hotel room. This is the most affordable month to lock in a stay. Prices are at their highest in , so avoid traveling during this time if your budget is tight. are the high season months for Sherwood. You'll need to book in advance and be ready to pay premium prices. are the least popular months to visit.
Which airport is best for Sherwood?
Washington, DC (DCA-Ronald Reagan Washington National) (64 kilometersaway from the downtown area), Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) (55 kilometersaway from central Sherwood) and Washington, DC (IAD-Washington Dulles Intl.) (100 kilometersaway from central Sherwood) are the main hubs in Sherwood.
Where should I stay when visiting Sherwood?
The Lowes Wharf Marina Inn is recommended by many visitors. Book as soon as possible before it's too late.
Can I go on vacation to Sherwood at this time?
Don't plan your trip to Sherwood without the facts about quarantine policies and travel restrictions. Travelocity's Covid-19 Travel Advisor will fill in the blanks. Our travel experts have pulled together all the info you need to make your vacation as hassle-free as possible.

Photos of local treasures

Browse Sherwood vacation photos for more inspiration

A large brick house with a green roof, surrounded by lush gardens and trees.