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Top Sherwood hotels

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $183 total per night from Sep 2 to Sep 3
$183 total
Sep 2 - Sep 3
Total includes 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, ...
"Every boat show this is my go to spot."

Reviewed on Aug 17, 2025

Graduate by Hilton Annapolis
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $115 total per night from Aug 24 to Aug 25
$115 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...
"from the moment we arrived, every person encountered was great!!! I especially Nicole at the front desk. I would definitely, definitely be coming back"

Reviewed on Aug 15, 2025

SpringHill Suites by Marriott Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $163 total per night from Aug 25 to Aug 26
$163 total
Aug 25 - Aug 26
Total includes 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. ...
"Nice size room (#3329), clean, comfortable and quiet - everything we ask for in a hotel room! Front office staffer and valet team friendly and helpful. Hotel itself is an easy walk to all the shopping and restaurants. Would definitely stay here again."

Reviewed on Aug 15, 2025

Historic Inns of Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $108 total per night from Sep 7 to Sep 8
$108 total
Sep 7 - Sep 8
Total includes 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. ...
"Well equipped, clean, and convenient, with plenty of room. Amenities."

Reviewed on Aug 17, 2025

Sonesta ES Suites Annapolis
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $283 total per night from Aug 25 to Aug 26
$283 total
Aug 25 - Aug 26
Total includes 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 ...
"#1 family get away. Kids absolutely love the pool."

Reviewed on Aug 14, 2025

Hyatt Regency Chesapeake Bay
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
$104 nightly
The price is $119 total per night from Aug 28 to Aug 29
$119 total
Aug 28 - Aug 29
Total includes 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. ...
"Good location"

Reviewed on Aug 12, 2025

Crowne Plaza Annapolis by IHG
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $212 total per night from Aug 24 to Aug 25
$212 total
Aug 24 - Aug 25
Total includes 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 ...
"Basic hotel 4 stars, does not have upscale rooms. Left a day early as my next day flight was canceled and the hotel refused to credit me the night I missed. Very unfriendly staff."

Reviewed on Aug 15, 2025

The Westin Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $110 total per night from Aug 31 to Sep 1
$110 total
Aug 31 - Sep 1
Total includes 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. ...
"Convince"

Reviewed on Aug 14, 2025

DoubleTree by Hilton Hotel Annapolis
Best Western Annapolis

Best Western Annapolis

2.5 out of 5
2520 Riva Rd, Annapolis, MD
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $87 total per night from Aug 20 to Aug 21
$87 total
Aug 20 - Aug 21
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the ...
"Good customer service at the desk. The area seemed a little sketchy, it sounded like someone tried to open our door, and there were a couple of people just waiting in their cars when we were checking in at 10pm."

Reviewed on Aug 17, 2025

Best Western Annapolis
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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.

Sherwood Hotel & Travel Guide\n

If you are intending on journeying through Eastern Chesapeake Shore and would like to stop by Sherwood, you would do well to book as soon as you can through Travelocity's hotels page so that you find the most suitable place to stay at. Sherwood offers 6 short and long-stay options within a 6-mile (10-kilometer) radius of the town center.

Are you wanting to find a place to stay that is a short walk to the middle of Sherwood? The Tilghman Island Inn and Lowes Wharf Marina Inn has you covered.

You could also check out the Inn at Perry Cabin by Belmond along with the Annapolis Waterfront Hotel, Autograph Collection. The Inn at Perry Cabin by Belmond can be found just 6 miles (10 kilometers) from the main part of Sherwood. The Annapolis Waterfront Hotel, Autograph Collection, is situated only 18 miles (29 kilometers) away. The Historic Kent Manor Inn as well as the Five Gables Inn and Spa are alternate places to base yourself in Sherwood.

For those who are wanting to check out some more of the coastal plains and wetlands that are a big feature in this area of United States of America, you would be wise to also plan some time in other destinations in Eastern Maryland. Modern travelers can see the area's attractions or enjoy ice fishing, hiking and shore fishing and afterwards reserve a suitable Travelocity-listed hotel to stay the night.

St. Michaels is 6 miles (10 kilometers) northeast of Sherwood and is where you'll find Chesapeake Bay Maritime Museum and St. Michaels Museum. The Harbourtowne St. Michaels and St Michaels Inn are a few of the convenient apartment and hotel alternatives in St. Michaels. 25 miles (41 kilometers) north of Sherwood, you'll find Rock Hall, which boasts the Mariners Motel and Inn at Osprey Point. The Mainstay and Rock Hall Harbor are some more popular attractions to explore in Rock Hall.

Baltimore Washington International Thurgood Marshall Airport is 35 miles (56 kilometers) away from Sherwood's city center. Travelers who hope to find accommodation in the area can easily secure a good option in the Residence Inn by Marriott Baltimore BWI Airport or the BWI Airport Marriott.

Frequently asked questions

What are the top kid-friendly hotels in Sherwood?
Take some of the struggles out of traveling with young ones by choosing a family-friendly Sherwood hotel. From well-thought-out amenities to extra-helpful services, these properties feature perks that'll make your visit go off without a hitch: You'll be well looked after at Lowes Wharf Marina Inn. It comes with a nearby beach, pet-friendly facilities and a commitment to making families feel at home. Also check out Waterfront-Private 153 acre Historic Estate. It offers a swimming pool, a travel crib and plenty of opportunities to spend time together.
Where can I find cheap hotels in Sherwood?
At Travelocity you'll find really nice hotels in Sherwood at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Sherwood rather than in Sherwood. We may find you even better rates, too.
How do I find the best Sherwood hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Sherwood then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Sherwood?
The cheapest hotel in Sherwood is $87. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Sherwood?
There are 1,184 hotels in Sherwood on Travelocity.
What are the best hotels in Sherwood?
Sherwood has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Sherwood for you!
When is the best time to visit Sherwood?
If you want the joy of a fun-filled trip in peak season, visit Sherwood during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Sherwood?
Based on historic data is usually the cheapest month to visit Sherwood. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Sherwood?
There are multiple hotels in Sherwood that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Sherwood. We have plenty of kid-friendly hotels in Sherwood to choose from on Travelocity!
Why book a hotel in Sherwood through Travelocity?
Because we have the top hotels in Sherwood! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Sherwood on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

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