Woolford
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Visit Woolford
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
Stay at this vacation home in Woolford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad ...
9.6/10 Exceptional! (36 reviews)
"Lots of space for our group! Had a great sunroom where our kids all played. It was clean and we also appreciated how much was provided in the kitchen."
Reviewed on Oct 12, 2026
St Michaels Inn
1228 S Talbot Street St. Michaels MD
The price is CA $104 per night from Dec 8 to Dec 9
CA $104
CA $114 total
Dec 8 - Dec 9
includes taxes & fees
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very good! (1,004 reviews)
"Front desk staff was pleasant and very accommodating. Housekeeping came every day with clean towels, as needed and to straighten up the room. We would definitely stay here again!"
Reviewed on Nov 6, 2026
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
The price is CA $204 per night from Nov 23 to Nov 24
CA $204
CA $272 total
Nov 23 - Nov 24
includes taxes & fees
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,004 reviews)
"What a beautiful location on the Choptank River! Clean room, comfortable bed, and lots of activities: stores at the huge fireplace, movies at the indoor pool, putt putt golf, and a hayride! Along with a spa! Food was delicious. A truly wonderful fall getaway."
Reviewed on Nov 6, 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.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
Stay at this vacation home in Woolford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad ...
9.6/10 Exceptional! (36 reviews)
"Lots of space for our group! Had a great sunroom where our kids all played. It was clean and we also appreciated how much was provided in the kitchen."
Reviewed on Oct 12, 2026
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
Woolford MD
Book a stay at this beach vacation home in Woolford. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Ragged Island and Spocott Windmill ...
9.8/10 Exceptional! (80 reviews)
"Everyone enjoyed the pool, dock, beach,screened in porch. They have two refrigerators, bike helmets, toddler toilet seat, step stool on third floor. Bring room darkening shades for anyone who likes to sleep late. Two baby gates for the stairs were wonderful. Bring sand toys and water shoes for all. ..."
Reviewed on Sep 1, 2026
Private 2 Acre Waterfront Family Retreat with Pool & Pier
Cambridge MD
Book a stay at this family-friendly vacation home in Cambridge. Enjoy free WiFi, private pools, and a garden. Popular attractions Christ Rock Park and Spocott ...
9.6/10 Exceptional! (99 reviews)
"House was grateful and host was super responsive."
Reviewed on Oct 20, 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.
Stay near popular Woolford attractions
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