Deals on vacations and trips to Sherwood

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Sherwood flight + hotel vacation packages

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Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $950, price is now $797 per person
$797
per person
Sep 3 - Sep 7
found 22 hours ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
This hotel features free self parking and express check-in. Express check-out is also provided.
Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $2,813, price is now $2,227 per person
$2,227
per person
Sep 24 - Sep 27
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was $2,016, price is now $1,610 per person
$1,610
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Dine at the beachfront restaurant and relax with beach umbrellas. Family-friendly amenities include an arcade/game room and kid-friendly dining, along with volleyball.
Monte Carlo Boardwalk Oceanfront Ocean City

Monte Carlo Boardwalk Oceanfront Ocean City

3 out of 5
Downtown Ocean City
Price was $1,991, price is now $1,624 per person
$1,624
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like free self parking and WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.
Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Price was $1,087, price is now $891 per person
$891
per person
Sep 3 - Sep 7
found 22 hours ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.

Top Sherwood hotels deals

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road Sherwood MD
$150 nightly
The price is $165 total per night
$165 total
Aug 2 - Aug 3
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
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$147 nightly
The price is $168 total per night
$168 total
Aug 5 - Aug 6
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.
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
$98 nightly
The price is $111 total per night
$111 total
Aug 2 - Aug 3
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.
Pet friendly
Parking included
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Free Cancellation
$118 nightly
The price is $134 total per night
$134 total
Aug 16 - Aug 17
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.
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
$88 nightly
The price is $97 total per night
$97 total
Aug 27 - Aug 28
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the conference center and conference space on site. Enjoy the seasonal outdoor pool and conveniences like a terrace and laundry facilities.
Pool
Breakfast included
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
$288 nightly
The price is $327 total per night
$327 total
Aug 13 - Aug 14
Total with taxes and fees
This smoke-free resort features a private beach, a golf course, and a full-service spa. Bring the family and enjoy the children's club, mini golf, and children's pool. Enjoy the 2 outdoor pools and perks like free self parking and free WiFi.
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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

Frequently asked questions

How much are vacation packages to Sherwood?
Travelocity has flight and hotel vacation packages starting as low as $797. 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

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