Book Exclusive Sherwood Vacation Packages

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Sherwood flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
Price was CA $761, price is now CA $730 per person
CA $730
per person
Apr 10 - Apr 14
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Rolling Road Park and Historical Society of Kent County Maryland are located nearby.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was CA $1,283, price is now CA $1,259 per person
CA $1,259
per person
Apr 10 - Apr 14
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Dorchester County Historical Society and Bay Country Shop are located nearby.
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 out of 5
Price was CA $1,063, price is now CA $1,044 per person
CA $1,044
per person
Apr 10 - Apr 14
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Grasonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Chesapeake Bay Environmental Center and Queenstown Harbor Golf Club are located nearby.
Quality Inn

Quality Inn

2.5 out of 5
Price was CA $874, price is now CA $874 per person
CA $874
per person
Apr 11 - Apr 15
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
Stay at this hotel in Grasonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chesapeake Bay Environmental Center and Queenstown Harbor Golf Links are located nearby.

Top Sherwood hotels deals

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road Tilghman MD
Free cancellation
Reserve now, pay when you stay
The price is CA $136 per night
CA $136
CA $150 total
Feb 17 - Feb 18
includes taxes & fees
Stay at this hotel in Tilghman. 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
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
Free cancellation
Reserve now, pay when you stay
The price is CA $124 per night
CA $124
CA $141 total
Mar 8 - Mar 9
includes taxes & fees
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Annapolis Harbor Center Shopping Center and Annapolis Harbour Center are located nearby.
Pool
Breakfast 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 $220 per night
CA $220
CA $251 total
Feb 23 - Feb 24
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 Civil Rights Plaque and ARTFX Gallery of Fine Crafts and Arts are located nearby.
Pet-friendly
Free WiFi
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
Get rates
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 The Colonial Players and 97, 99 and 101 East Street are located nearby.
Pet-friendly
Free WiFi
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
Free cancellation
Reserve now, pay when you stay
The price is CA $137 per night
CA $137
CA $156 total
Feb 22 - Feb 23
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 helpful staff and the clean rooms in our reviews. Popular attractions Annapolis Civil Rights Plaque and ARTFX Gallery of Fine Crafts and Arts 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 $143 per night
CA $143
CA $163 total
Mar 3 - Mar 4
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 Mall Shopping Center and Westfield Annapolis Mall are located nearby.
Pool
Parking included
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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.

Popular places to visit

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.

Back Creek Community Park

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.

Goat Island

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 $730, 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

Gardens and large home at Sherwood Gardens Park, in Baltimore, M
Gardens and large home at Sherwood Gardens Park, in Baltimore, M