Woolford Travel Guide

Tourist Guide

A group of white birds flying over a field of dry grass.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
Stay at this holiday home in Woolford. Enjoy free Wi-Fi, 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 12 Oct 2026

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
The price is NZ$147 per night from 6 Dec to 7 Dec
NZ$147
6 Dec - 7 Dec
includes taxes & fees
Stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
St Michaels Inn
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
The price is NZ$344 per night from 23 Nov to 24 Nov
NZ$344
23 Nov - 24 Nov
includes taxes & fees
Stay at this beach resort in Cambridge. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (1,003 reviews)
"The staff at the front desk were friendly and helpful."

Reviewed on 5 Nov 2026

Hyatt Regency Chesapeake Bay
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

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
Stay at this holiday home in Woolford. Enjoy free Wi-Fi, 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 12 Oct 2026

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
 Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted

Woolford MD
Stay at this beach holiday home in Woolford. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Ragged Island and Spocott Windmill are located ...
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 1 Sept 2026

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge MD
Stay at this family-friendly holiday home in Cambridge. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Christ Rock Park and Spocott Windmill ...
9.6/10 Exceptional! (99 reviews)
"House was grateful and host was super responsive."

Reviewed on 20 Oct 2026

Private 2 Acre Waterfront Family Retreat with Pool & Pier
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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