Deals on vacations and trips to Sherwood

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Sherwood flight + hotel vacation packages

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Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $661, price is now $606 per person
$606
per person
Dec 15 - Dec 19
found 1 day 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 WiFi.
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $2,562, price is now $1,919 per person
$1,919
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
This hotel features free self parking and express check-in. Express check-out is also provided.
Oceanic Motel

Oceanic Motel

2 out of 5
Downtown Ocean City
Price was $2,656, price is now $2,219 per person
$2,219
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this motel. WiFi in public areas is free. A terrace and a picnic area are also provided.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $751, price is now $650 per person
$650
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
This aparthotel features a seasonal outdoor pool and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning and laundry facilities are also provided.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,180, price is now $1,037 per person
$1,037
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

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
$100 nightly
The price is $110 total per night
$110 total
Nov 9 - Nov 10
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
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $120 total per night
$120 total
Dec 3 - Dec 4
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
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Free Cancellation
Reserve now, pay when you stay
$173 nightly
The price is $192 total per night
$192 total
Nov 17 - Nov 18
Total with taxes and fees
A marina, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Make the most of the 24-hour gym and seasonal outdoor pool, and relax with drinks at one of the 2 bars/lounges.
Pool
Restaurant
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Free Cancellation
$103 nightly
The price is $117 total per night
$117 total
Dec 6 - Dec 7
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
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
Free Cancellation
Reserve now, pay when you stay
$82 nightly
The price is $93 total per night
$93 total
Nov 29 - Nov 30
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Pool
Breakfast included
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
Nov 10 - Nov 11
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
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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 $606. 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.