Find 4 Star Hotels in Sherwood, MD from AED 319

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Sherwood 4 Star Hotels

Our top choices for Sherwood 4-star hotels

Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1014)
"Great place!"
United States
Tawnya
The price is AED 280
AED 319 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Hotel Annapolis
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1002)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is AED 481
AED 548 total
includes taxes & fees
21 Dec - 22 Dec
Graduate by Hilton Annapolis
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4.0 star property
Cambridge
8.8 out of 10, Excellent, (1001)
"Very courteous staff."
United States
Joseph
The price is AED 652
AED 840 total
includes taxes & fees
15 Dec - 16 Dec
Hyatt Regency Chesapeake Bay
Room, 2 Queen Beds, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (881)
"Great location, nice and clean "
United States
Micah
The price is AED 652
AED 744 total
includes taxes & fees
15 Dec - 16 Dec
Annapolis Waterfront Hotel, Autograph Collection
View from property
The Westin Annapolis

The Westin Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
"Spectacular "
United States
Dennis
The price is AED 566
AED 645 total
includes taxes & fees
14 Dec - 15 Dec
The Westin Annapolis
Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is AED 391
AED 507 total
includes taxes & fees
2 Jan - 3 January 2026
Rod 'N' Reel Resort
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
9.4 out of 10, Exceptional, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is AED 675
AED 843 total
includes taxes & fees
14 Dec - 15 Dec
The Inn at Chesapeake Bay Beach Club
Front of property
The Oaks Waterfront

The Oaks Waterfront

4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
"Loved the Oaks! Fabulous accommodations and excellent staff"
United States
Barbara
The price is AED 1,517
AED 1,669 total
includes taxes & fees
10 Dec - 11 Dec
The Oaks Waterfront
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Sherwood.
Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
The price is AED 1,783 per night from Dec 18 to Dec 19
AED 1,783
AED 2,157 total
18 Dec - 19 Dec
includes taxes & fees
9.4/10 Exceptional! (370 reviews)
Still don't see what you're looking for?
See all properties in Sherwood.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great"
stephen 3-night trip
Posted 13 hours ago
DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Sherwood?
With Expedia's handy filter tool, landing a great deal on a 4-star hotel in Sherwood just got simpler. Start by entering your chosen travel dates and length of your getaway. Then sort the results by price and pick the option that best suits your style and budget.

  • Search for the lowest price from AED 2,157

What's the difference between 5-star and 4-star hotels in Sherwood?
If you choose to book a stay at a 4-star hotel in Sherwood, you'll usually find lots of amenities to ensure you're relaxed, such as a gym, restaurant and pool. You can experience high-quality service and upscale accommodations. Choose a 5-star hotel and you'll have access to a few extra bells and whistles — think on-site spas, concierge assistance and nightly turndown services. You're likely to get extra amenities and first-rate services at a 5-star retreat, though both are awesome options for luxury guests.
Does Sherwood have any 4-star all-inclusive resorts?
Finding vacation bliss in Sherwood is as easy as entering your dates and destination, and selecting our "All inclusive" filter. Stay and play where just about everything is already taken care of like your accommodations, food, activities and entertainment, or choose a standard 4-star resort in or around this much-loved destination.

Explore a world of travel with Expedia