Book Hotels in Sherwood, MD

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Top Sherwood hotels

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Sherwood MD
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Wonderful for our needs this Thanksgiving. Playroom was full of blocks, books and puzzles. Hot tub was the best!! Kitchen is so well stocked!

Reviewed on Nov 30, 2025

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Opens in a new window6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
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 7 to Jan 8
$167 total
Jan 7 - Jan 8
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, ...
Room was spotless. The staff was helpful

Reviewed on Dec 16, 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 4 to Jan 5
$193 total
Jan 4 - Jan 5
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. ...
Best place to stay is the main building

Reviewed on Dec 22, 2025

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
$212 nightly
The price is $241 total per night from Jan 9 to Jan 10
$241 total
Jan 9 - Jan 10
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 ...
THE ROOM WAS CLEAN AND BEDS WERE COMFORTABLE THE STAFF WAS FRIENDLY THE LOCATION WAS PERFECT I WOULD STAY THERE AGAIN ON BAD THING THE COFFEE MACHINE AND THE COFFEE WERE BAD SWITCH TO A BETTER COFFEE

Reviewed on Dec 27, 2025

Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
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
$75 nightly
The price is $85 total per night from Jan 4 to Jan 5
$85 total
Jan 4 - Jan 5
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. ...
did not dine in your hotel.

Reviewed on Dec 24, 2025

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
$106 nightly
The price is $121 total per night from Feb 1 to Feb 2
$121 total
Feb 1 - Feb 2
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. ...
Everything was good - only minor negatives: 1) bathroom sink drained verrrrrry slowly 20-30 min to drain the sink completely. 2) bedding had an odd smell, though it didn’t seem unclean. 3) the tub has a significant slope to the center, which is scary; when it’s wet, especially when there’s soap residue; ...

Reviewed on Dec 27, 2025

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
$192 nightly
The price is $218 total per night from Jan 20 to Jan 21
$218 total
Jan 20 - Jan 21
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 ...
Clean room

Reviewed on Dec 26, 2025

Opens in a new windowHyatt Regency Chesapeake Bay
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $158 total per night from Jan 2 to Jan 3
$158 total
Jan 2 - Jan 3
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 ...
Beautiful and perfect location

Reviewed on Dec 22, 2025

Opens in a new windowThe Westin Annapolis
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
$83 nightly
The price is $95 total per night from Jan 15 to Jan 16
$95 total
Jan 15 - Jan 16
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 ...
Excellent

Reviewed on Dec 27, 2025

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 $85. 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 1,149 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 5 days ago
Travelocity Verified Review
"Excellent"
A verified traveler stayed at Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown

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