Deals on vacations and trips to Sherwood

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Sherwood flight + hotel vacation packages

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Crystal Beach Hotel

Crystal Beach Hotel

2.5 out of 5
Downtown Ocean City
Price was $424, price is now $398 per person
$398
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Salisbury (SBY)
This smoke-free hotel features 2 outdoor pools, a gym, and a restaurant. Enjoy the seasonal outdoor pool and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $527, price is now $447 per person
$447
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
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 $657, price is now $581 per person
$581
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Salisbury (SBY)
This hotel features a seasonal outdoor pool and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $804, price is now $713 per person
$713
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Salisbury (SBY)
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.
Best Western Salisbury Plaza

Best Western Salisbury Plaza

2.5 out of 5
Price was $619, price is now $575 per person
$575
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a seasonal outdoor pool on site, and a 24-hour front desk and a picnic area are also provided.

Top Sherwood hotels deals

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood MD
Get rates
This vacation home features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden and barbecue grills are also provided.
Pool
Kitchen
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
$147 nightly
The price is $167 total per night
$167 total
Jan 22 - Jan 23
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
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
$169 nightly
The price is $193 total per night
$193 total
Jan 18 - Jan 19
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
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $212 total per night
$212 total
Feb 1 - Feb 2
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 24-hour business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and laundry facilities and concierge services 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
$106 nightly
The price is $121 total per night
$121 total
Feb 11 - Feb 12
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
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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

Frequently asked questions

How much are vacation packages to Sherwood?
Travelocity has flight and hotel vacation packages starting as low as $398. 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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