Deals on vacations and trips to Sherwood

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Sherwood flight + hotel vacation packages

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Sea Bay Hotel

Sea Bay Hotel

2.5 out of 5
Midtown Ocean City
Price was $608, price is now $562 per person
$562
per person
Apr 17 - Apr 19
found 6 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, luggage storage, and laundry facilities are also on offer.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $678, price is now $612 per person
$612
per person
Apr 17 - Apr 19
found 6 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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 self parking and free WiFi.
Surf Villa Apartments

Surf Villa Apartments

3 out of 5
Midtown Ocean City
Price was $723, price is now $667 per person
$667
per person
Apr 17 - Apr 19
found 6 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Aloft Ocean City

Aloft Ocean City

3 out of 5
Midtown Ocean City
Price was $706, price is now $656 per person
$656
per person
Apr 17 - Apr 19
found 6 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Enjoy the indoor pool and perks like free WiFi. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was $690, price is now $642 per person
$642
per person
Apr 17 - Apr 19
found 6 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.

Top Sherwood hotels deals

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
$75 nightly
The price is $85 total per night
$85 total
Feb 8 - Feb 9
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
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
$149 nightly
The price is $170 total per night
$170 total
Jan 30 - Jan 31
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.
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
$101 nightly
The price is $115 total per night
$115 total
Feb 15 - Feb 16
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
Free Cancellation
Reserve now, pay when you stay
$184 nightly
The price is $210 total per night
$210 total
Feb 16 - Feb 17
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
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
$211 nightly
The price is $240 total per night
$240 total
Jan 28 - Jan 29
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.
On private beach
Pool
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $170 total per night
$170 total
Jan 25 - Jan 26
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this Beaux Arts hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and snack bar/deli.
Pool
Spa
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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 $562. 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

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