Woolford Holiday Packages
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Top Woolford hotels
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
Woolford MD
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted: Family-friendly holiday home with free WiFi and an outdoor pool. Located on the waterfront.
"Everything was great . Only problem was the bugs outside biting us"
Reviewed on 29 July 2026
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks: Pet-friendly holiday home with free WiFi and parking.
"We you this place for the groomsmen’s house and it was perfect! They allow multiple cars to be parked I. The driveway which is super helpful especially when you have multiple people coming from different places. The kitchen and table was excellent we were able to sit everyone around the table and ..."
Reviewed on 2 July 2026
St Michaels Inn
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
The price is AU$139 per night from 31 Aug to 1 Sept
AU$139
31 Aug - 1 Sept
includes taxes & fees
St Michaels Inn: Business-friendly hotel with free breakfast and free WiFi. Located in a shopping district.
"Lady behind the desk was lovely but otherwise horrible experience. Room was not clean with dirt everywhere and when I pulled back the sheets there was hair and semen in the sheets. I found this disturbing and got out as soon as I could. I also waited 30 minutes at check in before I even got checked ..."
Reviewed on 13 Aug 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.
