Woolford Vacations

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Find the Best Woolford Vacation Packages

Woolford Hotel Deals

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

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

Woolford MD
9.8/10 Exceptional! (58 reviews)
We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family.

Reviewed on Aug 24, 2025

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

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
9.4/10 Exceptional! (21 reviews)
House was wonderful, it had something for all ages, plenty of room for our group of 17. We also had family that lived nearby by over for breakfast one morning and still plenty of room. Lots of utensils for all our cooking needs. House was very clean. Host was very responsive with a couple of questions ...

Reviewed on Oct 20, 2025

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is ¥28,534 per night from Dec 17 to Dec 18
¥28,534
¥36,621 total
Dec 17 - Dec 18
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Staff was fantastic, and although it was cooler due to the fall weather, there was still quite a few activities., Especially if you golf. Overall, slightly overpriced for the off-season in Cambridge, but clearly on point for warmer weather.

Reviewed on Nov 22, 2025

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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.