The Best 4 Star Hotels in Upper Hooper Island, MD from ￥46,891

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Our top choices for Upper Hooper Island 4-star hotels

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

Daily cooked-to-order breakfast for a fee

1. Hyatt Regency Chesapeake Bay

Cambridge

Sinan

￥34,687

￥46,891 total

includes taxes & fees

Aug 24 - Aug 25

2. Walk to Dtwn: Waterfront Eastern Shore Townhome!

Cambridge

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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Upper Hooper Island.

Swanendele Inn at St. Mary's Maryland

49946 Airedele Rd Ridge MD

￥50,442

￥55,991 total

Aug 7 - Aug 8

includes taxes & fees

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Pool Spa Hot tub Breakfast included Waterpark

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.

Top Upper Hooper Island Hotel Reviews

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."