Browse the Best Sherwood Resorts from CA $383

A large brick house with a green roof, surrounded by lush gardens and trees.

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Our top choices for Sherwood resorts

Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers

1. Hyatt Regency Chesapeake Bay

Cambridge

Sinan

CA $383 total

includes taxes & fees

Aug 26 - Aug 27

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Top Sherwood Hotel Reviews

Rod 'N' Reel Resort

10/10 Excellent

"Great stay, staff can be more knowledgeable about property amenities."

Hyatt Regency Chesapeake Bay

10/10 Excellent

"⭐⭐⭐⭐⭐ First-Class in Every Way From the moment we arrived until the day we reluctantly checked out, the Hyatt Regency Chesapeake Bay exceeded every expectation. This isn’t just a hotel—it’s a destination. We made the most of everything the resort has to offer. We spent hours relaxing by the beautiful pool with attentive waitress service, rented bikes to explore the property, took Sea-Doos out on the bay for an unforgettable afternoon, enjoyed a round of mini golf, and then retreated to our luxurious suite to unwind in comfort. Every experience was seamless and first class. What truly sets this resort apart is the staff. Every employee we encountered was genuinely friendly, welcoming, and eager to help. Their attention to detail and commitment to making our stay special never went unnoticed. The grounds are immaculate, the amenities are outstanding, and the entire resort strikes the perfect balance between luxury and relaxation. Whether you’re looking for adventure, a romantic getaway, or simply a place to recharge, this property delivers. We’ve stayed at many resorts over the years, and this one ranks among the very best. We left already talking about when we can come back. Five stars without hesitation."

Sonesta ES Suites Annapolis

10/10 Excellent

"My first time here and it was perfect! Room was spacious with a full kitchen, breakfast was delicious and had a variety, was able to use the pool and the grilling/bonfire area, as well as the basketball court. It was the perfect getaway for me and my family. I will have to come here again!"

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"We got in very late and needed to sleep, shower, have breakfast and go. We didn’t use any amenities. It was fine for our need. Bed was comfortable and didn’t smell like a dog had been in the room. The carpet had some spots at the entry and things were compact in size but it met all of our needs. The refrigerator had a freezer section which was great to regress ice packs for insulin bag. The bathroom was tiny but worked. (Close the toilet lid so things don’t fall from the narrow counter behind) The thing we missed was a bath floor mat so not to slip. I put a small towel down but not the best option. The light for the bathroom is at the entry alongside of the entry light which put me using my cell phone light so not to wake the sleeping roommate with a bright light. Like I said. It worked for us, but there are sacrifices for a longer stay."

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Sherwood Resorts information

Number of reviews	1,004
Accommodation	1 Resorts
Lowest Price	CA $383
Highest Price	CA $383

Frequently asked questions

What can I expect from a resort vacation in Sherwood?

You deserve to get away, and a resort is just the place to find all the services and amenities you need for a relaxing trip to Sherwood. One of the comfortable resort hotels in the surrounding area could be just what you're searching for, whether you want a luxurious suite, a state-of-the-art fitness center, or fun activities to try.

What's a top resort in Sherwood?

Our top-rated resort near Sherwood: Hyatt Regency Chesapeake Bay - Beach resort. 20.1 mi (32.3 km) from Sherwood. Features 2 outdoor pools, 3 restaurants, and a private beach. Popular for its pool.

What can I do in Sherwood?

Goat Island and Knapp's Narrows Marina & Inn are a few of the interesting sights to visit. Other attractions in the area include St. Michaels Winery and St. Michaels Marina.

What's the weather like in Sherwood?

The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 41°F. Average annual precipitation for Sherwood is 53 inches.

What's the best way to get to and around Sherwood?

Fly into Easton, MD (ESN-Easton - Newnam), which is located 14.1 mi (22.7 km) from the heart of the city. Otherwise, look for flights into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 52.1 mi (83.8 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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Treat yourself

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Check prices for these dates

Our top choices for Sherwood resorts

1. Hyatt Regency Chesapeake Bay

Top Sherwood Hotel Reviews

Rod 'N' Reel Resort

Hampton Inn & Suites Annapolis

DoubleTree by Hilton Hotel Annapolis

Hyatt Regency Chesapeake Bay

Sonesta ES Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Hyatt Place Kent Narrows & Marina

The Westin Annapolis

Crowne Plaza Annapolis by IHG

Find out more about Sherwood

Sherwood Resorts information

Frequently asked questions

Explore a world of travel with Expedia

Search Resort Hotels in Sherwood from CA $383

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sherwood resorts

1. Hyatt Regency Chesapeake Bay

Top Sherwood Hotel Reviews

Rod 'N' Reel Resort

Find out more about Sherwood

Sherwood Resorts information

Frequently asked questions

Explore a world of travel with Expedia