Book Hotels in Sherwood, MD

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Top Sherwood hotels

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
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 ...
What a spectacular home!! We all loved our stay and took advantage of the beautiful heated pool, dock, fire pit and playground. In the evening the pool table, ping pong and foosball were enjoyed by all. Stunning views, beautiful furnishings and comfortable bedding. Hopefully we will have occasion ...

Reviewed on Oct 20, 2025

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Opens in a new windowHeated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $167 total per night from Jan 12 to Jan 13
$167 total
Jan 12 - Jan 13
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, ...
Pleasant staff. Good location to walk to restaurants, shops.

Reviewed on Dec 30, 2025

Opens in a new windowGraduate by Hilton 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
$169 nightly
The price is $193 total per night from Jan 7 to Jan 8
$193 total
Jan 7 - Jan 8
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. ...
Staff was exceptionally friendly & helpful. Room clean & tastefully appointed. Location was perfectly situated in the old town & near antique stores, Main Street & the harbor. Great getaway!

Reviewed on Jan 1, 2026

Opens in a new windowHistoric Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $250 total per night from Jan 11 to Jan 12
$250 total
Jan 11 - Jan 12
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 ...
Was disappointed that I expected a balcony but got the parking lot view and no balcony. Rooms were changed from my reservation for a King bed to two full size beds without my knowledge. Beds were comfortable. Shower water pressure was not the best. Very beautiful downtown with lots of shopping and ...

Reviewed on Jan 2, 2026

Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
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
$91 nightly
The price is $104 total per night from Jan 26 to Jan 27
$104 total
Jan 26 - Jan 27
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. ...
The people were extremely nice. I asked for a room close to the elevator because I have trouble walking. They went out of their way to help with that.

Reviewed on Jan 1, 2026

Opens in a new windowSonesta ES Suites 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
$83 nightly
The price is $94 total per night from Jan 11 to Jan 12
$94 total
Jan 11 - Jan 12
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. ...
The room was excellent, and the staff was as well. Special kudos to Jody behind the desk. The hotel bar /restaurant is fantastic and the bartender, Carlos, was amazing! We had a great time in the bar ringing in the new year.

Reviewed on Jan 1, 2026

Opens in a new windowDoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
$110 nightly
The price is $125 total per night from Jan 10 to Jan 11
$125 total
Jan 10 - Jan 11
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. ...
Amazing staff and breakfast was delicious.

Reviewed on Jan 2, 2026

Opens in a new windowCrowne Plaza Annapolis by IHG
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $231 total per night from Jan 15 to Jan 16
$231 total
Jan 15 - Jan 16
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 ...
Great rooms, amenities, staff

Reviewed on Dec 29, 2025

Opens in a new windowHyatt Regency Chesapeake Bay
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $104 total per night from Jan 11 to Jan 12
$104 total
Jan 11 - Jan 12
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, free WiFi in public areas, and ...
Everything was clean and in working order in the room. Staff was friendly and efficient. Location was perfect. Would definitely stay here again.

Reviewed on Jan 2, 2026

Opens in a new windowHilton Garden Inn Annapolis Downtown
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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 $94. 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 1,156 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.

Recent Sherwood hotel reviews by fellow wanderers

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

5 out of 5
Posted 4 days ago
Travelocity Verified Review
"Everything was clean and in working order in the room. Staff was friendly and efficient. Location was perfect. Would definitely stay here again."
A verified traveler stayed at Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown

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