Compare and book 5 Star hotels in Sherwood, Maryland

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Check availability on Sherwood 5 Star Hotels

This weekend
5 Jun - 7 Jun
Next weekend
12 Jun - 14 Jun

Our top choices for Sherwood 5-star hotels

Breakfast, lunch, dinner and brunch served

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (387 reviews)
"Wonderful location with great views and amenities such as a fire pit"
United States
Craig
The price is 15.866.739 ₫
17.453.414 ₫ total
includes taxes & fees
21 Jun - 22 Jun
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, pool loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (15 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is 8.689.481 ₫
9.905.945 ₫ total
includes taxes & fees
9 Jun - 10 Jun
The Inn at Tacaro Estate
Dinner served

Inn at 202 Dover

Inn at 202 Dover
5.0 star property
Easton
10.0 out of 10, Exceptional, (14 reviews)
"Celebrated our 33rd anniversary here and enjoyed it thoroughly. Felt pampered and welcomed. Best B&B ever! Everything from the room to the food was exceptional. Every need was anticipated and met. Looking forward to our next visit. The quintessential "living like a king" experience."
United States
James
Inn at 202 Dover
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Sherwood.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD
The price is 3.094.409 ₫ per night from 7 Jun to 8 Jun
3.094.409 ₫
3.527.784 ₫ total
7 Jun - 8 Jun
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
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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.

Learn more about Sherwood

Explore the historic Sherwood Forest community with its charming waterfront homes and private marina along the Severn River. Nearby Annapolis offers sailing excursions, while local residents enjoy exclusive access to the community beach and tennis courts.

See all hotels in Sherwood
Gardens and large home at Sherwood Gardens Park, in Baltimore, M

Top Sherwood Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"We enjoyed a wonderful, stress-free four days at the inn and the surrounding area. Highly recommend it."
Keith 3-night trip
Posted 10 days ago
Inn at Perry Cabin

Frequently asked questions

What are the best 5-star hotels in Sherwood?
If you're seeking a 5-star experience, Inn at Perry Cabin offers one of the best of them based on reviews by our customers. Choose this Sherwood escape and get ready for amazing guest services, premium guest rooms and superior amenities.
How much does it cost to stay in a 5-star hotel in Sherwood?
You'll find several pricing options for a 5-star hotel in Sherwood on Expedia. How much you'll pay will depend on your travel dates, length of your trip and other factors. Compare all of the available accommodation for your desired dates and use our pricing and other filters to land the ideal luxury stay.

  • Search for the lowest price per night from 3.527.784 ₫

What makes a hotel 5 stars in Sherwood?
Impeccable guest service is the hallmark of every 5-star hotel in Sherwood. From the moment you arrive, staff attend to your every need, whether arranging valet parking or providing in-room beauty treatments. On top of that, hotels have to feature top-rate conveniences to obtain a 5-star rating. These can include luxury bathrooms, a wellness centre, swimming pools, fine dining restaurants and knowledgeable concierge.