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Top Sherwood hotels

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road Sherwood MD
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $165 total per night from Oct 14 to Oct 15
$165 total
Oct 14 - Oct 15
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 ...
"I will be back! Beautiful surroundings in a very well maintained, locally staffed (and guessing owned in conjunction with the marina), quaint hotel. The sound of the moored boats out front was soothing and the place was spic and span. Front desk staff are very friendly and great with ..."

Reviewed on Sep 28, 2026

Opens in a new windowKnapps Narrows Marina & Inn
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$119 nightly
The price is $136 total per night from Nov 11 to Nov 12
$136 total
Nov 11 - Nov 12
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. ...
"We stayed here overnight so that we didn't have to travel from MoCo to Annapolis for an early morning conference. We stayed in the Maryland Inn, it was quaint, very clean, and cute. We really enjoyed the property, its location to the water and the conference. We'd definitely stay here again."

Reviewed on Oct 13, 2026

Opens in a new windowHistoric Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$106 nightly
The price is $121 total per night from Oct 18 to Oct 19
$121 total
Oct 18 - Oct 19
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 staff at this hotel was very helpful, but the hotel design was meandering and confusing. I had a very long walk through twisting corridors to reach my room. No carts or bell staff seemed to be available."

Reviewed on Oct 13, 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
$107 nightly
The price is $122 total per night from Nov 11 to Nov 12
$122 total
Nov 11 - Nov 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. ...
"Clean room. Great breakfast."

Reviewed on Oct 13, 2026

Opens in a new windowCrowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
$95 nightly
The price is $108 total per night from Nov 8 to Nov 9
$108 total
Nov 8 - Nov 9
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 room smelled terrible like feet and dust and mildew. The smell was so strong i could not sleep through the night. The bathroom shower leaked all night and the curtains had a million little holes in them like bugs had been chewing through them. There was a roach walking across the kitchen ..."

Reviewed on Oct 13, 2026

Opens in a new windowSonesta ES Suites Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $146 total per night from Oct 21 to Oct 22
$146 total
Oct 21 - Oct 22
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 ...
"Beautiful property on the Chesapeake Bay. It was very clean. We went off season highly recommend."

Reviewed on Oct 11, 2026

Opens in a new windowRod 'N' Reel Resort
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
$106 nightly
The price is $121 total per night from Oct 25 to Oct 26
$121 total
Oct 25 - Oct 26
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 ...
"Room was awesome, very clean housekeeping staff extremely nice. Would suggest more help in the restaurant, food was excellent, poor waitress was running around trying to serve everyone!"

Reviewed on Oct 13, 2026

Opens in a new windowHilton Garden Inn Annapolis Downtown
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $98 total per night from Nov 1 to Nov 2
$98 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of ...
"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help ..."

Reviewed on Oct 13, 2026

Opens in a new windowSt Michaels Inn
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
$147 nightly
The price is $167 total per night from Oct 26 to Oct 27
$167 total
Oct 26 - Oct 27
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, ...
Opens in a new windowGraduate by Hilton Annapolis
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See all available properties in Sherwood
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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 $98. 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 1,170 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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Clean room. Great breakfast."
A verified traveler stayed at Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG

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