Find luxury hotels in Woolford, MD

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Check availability on Woolford Luxury Hotels

Our top choices for Woolford luxury hotels

Dock
Marvel's on the Creek

Marvel's on the Creek

Marvel's on the Creek
4.0 star property
East New Market
10.0 out of 10, Exceptional, (161)
"Clean & spacious room. Amazing hospitality. Excellent communication!"
United States
Chin
$184 nightly
The price is $205
Dec 17 - Dec 18
Total with taxes and fees
Marvel's on the Creek
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1002)
"Very courteous staff."
United States
Joseph
$184 nightly
The price is $209
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hyatt Regency Chesapeake Bay
Front of property
The Oaks Waterfront

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
$459 nightly
The price is $505
Dec 14 - Dec 15
Total with taxes and fees
The Oaks Waterfront
Breakfast, lunch, dinner served; ocean views
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
$535 nightly
The price is $588
Dec 18 - Dec 19
Total with taxes and fees
Inn at Perry Cabin
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.
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Top Woolford Hotel Reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience. "
Drexel 1-night trip
Posted 7 days ago
Hyatt Regency Chesapeake Bay

Frequently asked questions

Are you searching for the perfect hotel for your luxury holiday in Woolford?
Use Expedia to arrange your flight to Easton, MD (ESN-Easton - Newnam) airport, and then choose from a variety of places to stay that will deliver the luxury you seek. Amenities are an important consideration when you plan a vacation, so we make it easy to find what you need to make your stay special. If you want a posh hotel that has a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Woolford has to offer. Woolford has some interesting things to see and do including Blackwater National Wildlife Refuge and Woods Island, so you might want to take in the local sights during your visit.
When can I expect good weather in Woolford?
Planning for the weather is a good way to make your trip to Woolford relaxing and enjoyable, especially when you're splurging. 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 Woolford is 48 inches.
What's there to see and do in Woolford?
Experience Woolford with a stop at Blackwater National Wildlife Refuge, Harriet Tubman Underground Railroad National Historical Park, and Harriet Tubman Museum and Educational Center. If you have some spare time during your trip, you might want to check out Choptank River Lighthouse and Gerry Boyle Park at Great Marsh.

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