Maryland may have travel restrictions in place, including self-quarantine, due to COVID-19.

Find out moreOpens in new tab or window

Find Hotels in Sherwood, MD

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Filter by

Popular filters
Star rating
Your budget
Guest rating
Payment type
Property type
Neighborhood
Popular locations
Meal plans available
Amenities
Accessibility
Trip type
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $144 per night from Feb 1 to Feb 2
17.95 mi from city center
4.3/5Excellent! (330 reviews)

"Overlooks the water the bay USNA and DTA and is pet friendly"…"

Reviewed on Jan 15, 2021

Annapolis Waterfront Hotel, Autograph Collection
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
Get Rates
6.33 mi from city center
4.7/5Exceptional! (265 reviews)

"I have been to Inn at Perry Cabin Many times . Just love the place"…"

Reviewed on Mar 21, 2020

Inn at Perry Cabin
Best Western Annapolis

Best Western Annapolis

2.5 out of 5
2520 Riva Rd, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $55 per night from Jan 26 to Jan 27
19.96 mi from city center
3.5/5Good! (992 reviews)

"Your new bathrooms, about time someone upgraded. Thsnks"…"

Reviewed on Oct 7, 2020

Best Western Annapolis
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Sign up, it's freeSign in
Lowes Wharf Marina Inn

Lowes Wharf Marina Inn

3 out of 5
21651 Lowes Wharf Rd, Sherwood, MD
Free CancellationReserve now, pay when you stay
The price is $109 per night from Jan 27 to Jan 28
1.31 mi from city center
3.5/5Good! (28 reviews)

"Very enjoyable!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!"…"

Reviewed on Sep 7, 2020

Lowes Wharf Marina Inn
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 out of 5
3101 Main Street, Grasonville, MD
Free CancellationReserve now, pay when you stay
The price is $81 per night from Jan 26 to Jan 27
15.96 mi from city center
3.8/5Good! (682 reviews)

"Good value. Clean. Check in was a slow though. Would stay again"…"

Reviewed on Jan 16, 2021

Best Western Kent Narrows Inn
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

2.5 out of 5
8708 Alicia Drive, Easton, MD
Free CancellationReserve now, pay when you stay
The price is $84 per night from Jan 28 to Jan 29
14.79 mi from city center
4.8/5Exceptional! (789 reviews)

"Don’t stay anywhere else in Easton, MD. Always great service and hospitality"…"

Reviewed on Jan 11, 2021

Best Western Plus Easton Inn & Suites
The Oxford Inn

The Oxford Inn

3 out of 5
504 S Morris St, Oxford, MD
Free Cancellation
The price is $125 per night from Jan 26 to Jan 27
9.51 mi from city center
4.4/5Excellent! (49 reviews)

"Very nice place. Hospitable staff. Nice breakfast."…"

Reviewed on Oct 12, 2020

The Oxford Inn
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

3.5 out of 5
210 Holiday Court, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $84 per night from Jan 26 to Jan 27
20 mi from city center
4.2/5Very Good! (996 reviews)

"The staff were super helpful and personable. They were quick to answer questions and gave excellent recommendations for dining and sightseeing spots. Definitely will stay here again."…"

Reviewed on Dec 13, 2020

DoubleTree by Hilton Hotel Annapolis
Super 8 by Wyndham Prince Frederick

Super 8 by Wyndham Prince Frederick

2 out of 5
40 Commerce Ln, Rt 2 and Rt 4, Prince Frederick, MD
Free CancellationReserve now, pay when you stay
The price is $62 per night from Jan 31 to Feb 1
19.86 mi from city center
3.2/5 (179 reviews)

"Service was great , staff very nice Very clean But I feel like they need to change all the lamps in rooms they are all rusty, they should get better pillows and the rugs need need cleaning ."…"

Reviewed on Sep 8, 2020

Super 8 by Wyndham Prince Frederick
Graduate Annapolis

Graduate Annapolis

4 out of 5
126 West St, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $93 per night from Feb 1 to Feb 2
18.39 mi from city center
4.4/5Excellent! (992 reviews)

"Always love our stays at the Graduate! Highly recommend"…"

Reviewed on Jan 10, 2021

Graduate Annapolis
Extended Stay America Annapolis - Admiral Cochrane Drive

Extended Stay America Annapolis - Admiral Cochrane Drive

2.5 out of 5
120 Admiral Cochrane Dr, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $67 per night from Feb 15 to Feb 16
19.88 mi from city center
2.9/5 (543 reviews)

"Stayn here is more a home feel than a hotel feel. Would recommend."…"

Reviewed on Nov 22, 2020

Extended Stay America Annapolis - Admiral Cochrane Drive
Residence Inn by Marriott Annapolis

Residence Inn by Marriott Annapolis

3 out of 5
170 Admiral Cochrane Dr, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $77 per night from Feb 8 to Feb 9
19.68 mi from city center
4.4/5Wonderful! (272 reviews)

"Property located in near Aerospace Academy. Must have a vehicle"…"

Reviewed on Jan 2, 2021

Residence Inn by Marriott Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $76 per night from Jan 26 to Jan 27
18.24 mi from city center
4.5/5Wonderful! (989 reviews)

"Excellent front desk staff and comfortable rooms, would definitely recommend it"…"

Reviewed on Dec 5, 2020

Historic Inns of Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

3 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Free Cancellation
The price is $92 per night from Jan 29 to Jan 30
11.78 mi from city center
4/5Very Good! (399 reviews)

"Bay view is beautiful. Make sure you get a room with it."…"

Reviewed on Jan 24, 2021

Rod 'N' Reel Resort
Extended Stay America Annapolis - Womack Drive

Extended Stay America Annapolis - Womack Drive

2.5 out of 5
1 Womack Dr, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $67 per night from Feb 15 to Feb 16
19.45 mi from city center
2.7/5 (508 reviews)

"It was amazing"…"

Reviewed on Jul 16, 2020

Extended Stay America Annapolis - Womack Drive
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4 out of 5
180 Pier One Road, Stevensville, MD
Free CancellationReserve now, pay when you stay
The price is $179 per night from Jan 26 to Jan 27
15.92 mi from city center
4.6/5Exceptional! (216 reviews)

"Very nice & clean resort. Great for a quick getaway. The resort is small and not many activities or things to do in the winter."…"

Reviewed on Jan 6, 2021

The Inn at Chesapeake Bay Beach Club
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
The price is $76 per night from Jan 26 to Jan 27
6.7 mi from city center
4/5Very Good! (707 reviews)

"The room was very clean and the staff at front desk friendly. They had a recommendation for transportation for us into town so we didn't have to take our own vehicle. Even though breakfast wasn't available because of Covid, they had snacks out you could grab and go the next morning."…"

Reviewed on Dec 10, 2020

St Michaels Inn
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $77 per night from Jan 31 to Feb 1
19.47 mi from city center
4.5/5Wonderful! (997 reviews)

"Very clean, great staff. The jacuzzi tub is the best amenity!!!!!!"…"

Reviewed on Oct 3, 2020

SpringHill Suites by Marriott Annapolis
Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton

2.5 out of 5
8945 Sunflower Drive, Easton, MD
Free CancellationReserve now, pay when you stay
The price is $99 per night from Jan 29 to Jan 30
14.94 mi from city center
4.7/5Exceptional! (164 reviews)

"Great place to stay and relax. Will come again! Saw the lively sunrise from my room"…"

Reviewed on Dec 19, 2020

Fairfield Inn & Suites by Marriott Easton
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 out of 5
124 Womack Dr, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $68 per night from Jan 26 to Jan 27
19.73 mi from city center
4.2/5Very Good! (997 reviews)

"Room was spotless, good service and room space. Good for pet owners"…"

Reviewed on Dec 26, 2020

Hampton Inn & Suites Annapolis
Don't see what you're looking for?
See all available properties in Sherwood
View all properties
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.

Visiting Sherwood

Visitors can enjoy all that Sherwood has to offer including the waterfront and restaurants. This city also attracts tourists with its scenic and welcoming setting.

  • There are 2 hotels and other accommodations in Sherwood
  • The closest major airport is in Easton, MD (ESN-Easton - Newnam), 14.9 mi (23.9 km) from the city center
  • The next closest is in Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), 51.9 mi (83.6 km) away

Sightseeing and Staying in Sherwood

Places to visit in the larger region include Tilghman Watermen’s Museum, St. Michaels Winery, and St. Michaels Museum. In the area, you'll also find Chesapeake Bay Maritime Museum and Oxford Museum.

Below is a top place to stay based on our user reviews:

  • Lowes Wharf Marina Inn - With a stay at this 3-star inn, guests can enjoy access to a restaurant and free parking, along with free WiFi.

Dressing for Sherwood

  • Between January and March, daytime temperatures average 59°F, while nighttime temperatures stay around 26°F
  • From April to June, the average is 85°F during the day and 41°F at night
  • July through September sees average temperatures of 86°F during the day and 56°F at night
  • In October-December, you can expect 74°F as the daytime average and 28°F as the nighttime average
  • Average annual rainfall for Sherwood is 47.32 inches
  • July and August are usually the hottest months averaging 85°F, while January and February are usually the coldest with an average temperature of 28°F

Frequently asked questions

Where is the best place to stay in Sherwood?
Lowes Wharf Marina Inn is one of the top choices for your stay based on our traveler data. This 3-star inn offers a marina and a restaurant. Holidays at the Cove - plenty of space to gather while making memories is another good choice for your stay.
If I need to cancel my hotel reservation in Sherwood, will I receive a refund?
Yes, most room reservations are fully refundable if cancelled prior to the accommodation’s cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, you might still have the option to cancel and get a refund within 24 hours of booking. Plug in your dates, click on “Search”, then you can filter by “free cancellation” to review top deals in Sherwood.
Where can I learn more about changing or cancelling my trip to Sherwood?
To find more details about changing or cancelling your trip to Sherwood, head over to our customer service page.
What are some hotels with pools in Sherwood?
Holidays at the Cove - plenty of space to gather while making memories: Provides a sauna, an outdoor pool, and a hot tub. Hyatt Regency Chesapeake Bay and Courtyard by Marriott Annapolis are a couple of other choices that feature an onsite pool.

Recent reviews of Sherwood hotels

    Rod 'N' Reel Resort
    Expedia Verified Review…
    5 / 5 Excellent
    Bay view is beautiful. Make sure you get a room with it.…
    A verified traveler stayed at Rod 'N' Reel Resort
    Posted 18 hours ago
    Rod 'N' Reel Resort
    Hilton Garden Inn Annapolis Downtown
    Expedia Verified Review…
    5 / 5 Excellent
    Room wad immaculate, parking was convenient. And was nice to have a bar, restaurant in lobby …
    A verified traveler from Chesapeake stayed at Hilton Garden Inn Annapolis Downtown
    Posted 19 hours ago
    Hilton Garden Inn Annapolis Downtown
    Quality Inn
    Expedia Verified Review…
    5 / 5 Excellent
    The property was quiet clean and convient. My stay was only for a night but it was safe .Coffee was ready in the morning. No breakfast due to the coronavirus.…
    A verified traveler from Grasonville stayed at Quality Inn
    Posted 2 days ago
    Quality Inn
    Holiday Inn Express Cambridge
    Expedia Verified Review…
    5 / 5 Excellent
    Great Covid safety practices and also enjoyed the no noise after ten pm policy…
    A verified traveler from Cambridge stayed at Holiday Inn Express Cambridge
    Posted 3 days ago
    Holiday Inn Express Cambridge
    The Westin Annapolis
    Expedia Verified Review…
    5 / 5 Excellent
    Location was very good. Check in and out very easy. Staff very professional …
    A verified traveler from Ocean City Md stayed at The Westin Annapolis
    Posted 4 days ago
    The Westin Annapolis
    Parsonage Inn
    Expedia Verified Review…
    5 / 5 Excellent
    The building itself was gorgeous inside and out. It felt like you were time traveling to the Victorian era. There is an illusion sighting of a woman in white spirit. I didn’t see her but I felt her presence. The inn owner is hospitable and full of information. He gave great tips on where to eat and what to check out in town. Overall fantastic experience and I will recommend this inn to everyone I know. …
    A verified traveler from Baltimore stayed at Parsonage Inn
    Posted 9 days ago
    Parsonage Inn
    Annapolis Waterfront Hotel, Autograph Collection
    Expedia Verified Review…
    5 / 5 Excellent
    Overlooks the water the bay USNA and DTA and is pet friendly…
    A verified traveler stayed at Annapolis Waterfront Hotel, Autograph Collection
    Posted 9 days ago
    Annapolis Waterfront Hotel, Autograph Collection
    Hyatt Regency Chesapeake Bay
    Expedia Verified Review…
    5 / 5 Excellent
    I had a nice time and wish I could’ve stayed longer. …
    A verified traveler stayed at Hyatt Regency Chesapeake Bay
    Posted 11 days ago
    Hyatt Regency Chesapeake Bay
    Crowne Plaza Annapolis
    Expedia Verified Review…
    5 / 5 Excellent
    Great customer service. Asked for early check in and they accommodated without charging. Great price for quality …
    A verified traveler stayed at Crowne Plaza Annapolis
    Posted 11 days ago
    Crowne Plaza Annapolis

More trip options