Book Exclusive Sherwood Vacation Packages

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Sherwood flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Monte Carlo Ocean City

Hotel Monte Carlo Ocean City

3 out of 5
Downtown Ocean City
Price was CA $2,129, price is now CA $1,788 per person
CA $1,788
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
Book a stay at this family-friendly hotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was CA $2,542, price is now CA $1,997 per person
CA $1,997
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
Book a stay at this beach hotel in Fenwick Island. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maryland Beach and Northside Park are located nearby.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was CA $2,388, price is now CA $1,891 per person
CA $1,891
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maryland Beach and Ocean City Boardwalk are located nearby.
Monte Carlo Boardwalk Oceanfront Ocean City

Monte Carlo Boardwalk Oceanfront Ocean City

3 out of 5
Downtown Ocean City
Price was CA $2,451, price is now CA $1,949 per person
CA $1,949
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was CA $2,193, price is now CA $1,808 per person
CA $1,808
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
Book a stay at this beach aparthotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean City Boardwalk and Ocean City Beach 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
Free cancellation
Reserve now, pay when you stay
The price is CA $211 per night
CA $211
CA $232 total
Aug 3 - Aug 4
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.
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 $144 per night
CA $144
CA $165 total
Aug 23 - Aug 24
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 $150 per night
CA $150
CA $219 total
Aug 19 - Aug 20
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 Chesapeake Bay Bridge are located nearby.
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Free cancellation
Reserve now, pay when you stay
The price is CA $115 per night
CA $115
CA $127 total
Aug 17 - Aug 18
includes taxes & fees
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saint Michaels Village and Classic Motor Museum are located nearby.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Free cancellation
Reserve now, pay when you stay
The price is CA $358 per night
CA $358
CA $473 total
Aug 19 - Aug 20
includes taxes & fees
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.
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 $166 per night
CA $166
CA $189 total
Aug 12 - Aug 13
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.
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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.

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

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 $1,788, 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.