Woolford Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Woolford
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is S$414 per night from 1 Jun to 2 Jun
S$414
1 Jun - 2 Jun
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Hotel needs a big update. Very dated"
Reviewed on 17 May, 2026
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
The price is S$911 per night from 9 Jun to 10 Jun
S$911
9 Jun - 10 Jun
includes taxes & fees
9.6/10 Exceptional! (386 reviews)
"Wonderful location with great views and amenities such as a fire pit"
Reviewed on 18 May, 2026
The Wildset
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
The price is S$350 per night from 3 Jun to 4 Jun
S$350
3 Jun - 4 Jun
includes taxes & fees
9.8/10 Exceptional! (445 reviews)
"The overall vibe is super cute, but the bed was so mushy and the AC didn’t go down past 71. The poor woman who was the breakfast was seemingly overwhelmed, but not sure why as the spread was cold croissants, which could have been put into the oven to elevate the otherwise good granola and yogurt ..."
Reviewed on 20 May, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
