Deals on vacations and trips to Sherwood

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Sherwood flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

2.5 out of 5
Midtown Ocean City
Price was $750, price is now $603 per person
$603
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Salisbury (SBY)
A private beach and an outdoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Enjoy the indoor pool and perks like free self parking.
Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Price was $1,987, price is now $1,438 per person
$1,438
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Providence (PVD) to Salisbury (SBY)
Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $995, price is now $722 per person
$722
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Salisbury (SBY)
This hotel features 4 restaurants, an outdoor pool, and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free WiFi.
Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $1,312, price is now $1,031 per person
$1,031
per person
Jun 8 - Jun 13
found 9 hours ago
Roundtrip non-stop flight included
Providence (PVD) to Salisbury (SBY)
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. Luggage storage is also provided.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
Price was $1,165, price is now $930 per person
$930
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Salisbury (SBY)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Top Sherwood hotels deals

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road Sherwood MD
$100 nightly
The price is $110 total per night
$110 total
Mar 26 - Mar 27
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A picnic area is also provided.
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
$176 nightly
The price is $201 total per night
$201 total
Apr 12 - Apr 13
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Free Cancellation
$105 nightly
The price is $120 total per night
$120 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Parking included
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$157 nightly
The price is $179 total per night
$179 total
Apr 2 - Apr 3
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.
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
$105 nightly
The price is $120 total per night
$120 total
Mar 29 - Mar 30
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a snack bar/deli, and dry cleaning are also offered.
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
$89 nightly
The price is $102 total per night
$102 total
Mar 29 - Mar 30
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.
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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

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

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

Frequently asked questions

How much are vacation packages to Sherwood?
Travelocity has flight and hotel vacation packages starting as low as $603. With these kinds of bargains, you'll be saying hello to Sherwood in a flash.
How long should my Sherwood vacation be?
The majority of people lock in a hotel for 2 nights in Sherwood. But that doesn't mean you're limited to that. How long you spend here really comes down to what you hope to do on your vacation. If your aim is to discover every part of this superb location, book another night or two (or even an extra week!).
Where can I get the best vacation package deals for Sherwood?
You'll come across a fantastic range of Sherwood package deals on Travelocity. With 400 partner airlines and 1,000,000 worldwide properties, piecing together your ideal vacation will be simple.
Why should I book my Sherwood vacation bundle with Travelocity?
With our Price Match Guarantee, we'll match any lower price you're able to find. Add on our 24/7 support and high-quality service and the vacation you've been dreaming of is closer than ever before.
Can I save money on my Sherwood car rental if I bundle it with my hotel or flight?
Bundling your flight, hotel and car into a Sherwood vacation package is a great way to land the best deal. Plus, having your own set of wheels gives you absolute freedom to find your way to all those amazing sights you want to see. Located 40 mi from Sherwood, White House is one attraction that should be on your agenda. Top up the tank and make a day trip of it.
What is the best time of year to go to Sherwood?
Vacationing in the quieter months of the year, November, December and January, comes with a swag of benefits — think cheap airfares and hotels and less bumping shoulders with tourist crowds. But there's magic in the destination in the peak season. More events will be staged and more attractions will be open in May, June and July. If you're on a budget, generally offers the cheapest hotel prices. You can expect to pay more for a room in .
Which airport is best for Sherwood?
Ronald Reagan Washington National Airport (DCA) (40 mi away from downtown), Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (35 mi away from central Sherwood) and Salisbury - Ocean City Wicomico Regional Airport (SBY) (50 mi away from central Sherwood) are the main options in Sherwood.
Where should I stay when visiting Sherwood?
The Waterfront - Private 153 Acre Historic Estate is the number one choice of many travelers. Book now before it's too late.

Photos of local treasures

Browse Sherwood vacation photos for more inspiration

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