Title: Visit Woolford: Best of Woolford Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Woolford](https://expedia.ca/Woolford-Hotels.d553248635975865928.Travel-Guide-Hotels)[Vacation Rentals in Woolford](https://expedia.ca/Woolford-Vacation-Rentals.d553248635975865928.Travel-Guide-VacationRentals)[Woolford Car Rentals](https://expedia.ca/Car-Rentals-In-Woolford.d553248635975865928.Car-Rental-Guide)[Woolford Vacation Packages](https://expedia.ca/Woolford.d553248635975865928.Destination-Travel-Guides) # Woolford ## Travel Guide ## Visit Woolford Things to do - Woolford Hotel Deals - Vacation Rentals in Woolford ![ Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/w1624h1084x0y2-ec718b23_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock 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! (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 [Get rates](https://expedia.ca/Hotel-Search?startDate=03%2F12%2F2025&endDate=04%2F12%2F2025&selected=33549150&PinnedHotelID=33549150&HadPinnedHotel=true®ionId=553248635975865928) [](https://expedia.ca/Hotel-Search?startDate=03%2F12%2F2025&endDate=04%2F12%2F2025&selected=33549150&PinnedHotelID=33549150&HadPinnedHotel=true®ionId=553248635975865928) ![The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks](https://images.trvl-media.com/lodging/96000000/95860000/95854100/95854099/60be688f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 ... 9.4/10 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 [Get rates](https://expedia.ca/Hotel-Search?startDate=03%2F12%2F2025&endDate=04%2F12%2F2025&selected=95854099&PinnedHotelID=95854099&HadPinnedHotel=true®ionId=553248635975865928) [](https://expedia.ca/Hotel-Search?startDate=03%2F12%2F2025&endDate=04%2F12%2F2025&selected=95854099&PinnedHotelID=95854099&HadPinnedHotel=true®ionId=553248635975865928) ![Hyatt Regency Chesapeake Bay](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Chesapeake Bay 100 Heron Blvd Cambridge MD Fully refundable CA $234 CA $303 total Dec 15 - Dec 16 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. ... 8.6/10 Excellent! (1,000 reviews) The room was spotless. The staff were courteous and helpful. Fantastic hotel! Reviewed on Oct 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=15%2F12%2F2025&endDate=16%2F12%2F2025&selected=890486&PinnedHotelID=890486&HadPinnedHotel=true®ionId=553248635975865928) [See all 513 properties in Woolford](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=20%2F11%2F2025&endDate=21%2F11%2F2025®ionId=553248635975865928) 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. ![ Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/w1624h1084x0y2-ec718b23_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock 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! (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 [](https://expedia.ca/Woolford-Hotels-Newer-Luxury-Waterfront-Beach.h33549150.Hotel-Information) ![The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks](https://images.trvl-media.com/lodging/96000000/95860000/95854100/95854099/60be688f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 ... 9.4/10 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 [](https://expedia.ca/Woolford-Hotels-The-Blue-Heron-Spacious-Waterfront-Eastern-Shore-Getaway-With-Kayaks.h95854099.Hotel-Information) ![Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay](https://images.trvl-media.com/lodging/24000000/23930000/23921900/23921839/7094a412_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay Port Republic MD Book a stay at this beach cabin in Port Republic. Enjoy free WiFi, a beach locale, and a garden. Popular attractions CSA Park and R&J's PlayPark are located ... 9.8/10 Exceptional! (178 reviews) Hubby and I loved our stay in this rustic cabin. It is above the water with unobstructed views. We saw a LOT of birds during our stay. There were many Osprey flying around and catching their breakfasts/dinners right in front of us! There were bald eagles in the neighbors tree. Brett is very helpful ... Reviewed on Oct 6, 2025 [](https://expedia.ca/Port-Republic-Hotels-Stunning-Views-From-Waterfront-Log-Cabin-With-Fireplace-On-The-Chesapeake-Bay.h23921839.Hotel-Information) [See all properties in Woolford](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=553248635975865928&sort=VACATION_RENTAL) 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. ## Check Woolford hotel availability [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-19&endDate=2025-11-20) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-19&endDate=2025-11-20) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-19&endDate=2025-11-20) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-19&endDate=2025-11-20)[Nov 19 - Nov 20](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-19&endDate=2025-11-20) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-20&endDate=2025-11-21) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-20&endDate=2025-11-21) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-20&endDate=2025-11-21) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-20&endDate=2025-11-21)[Nov 20 - Nov 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-20&endDate=2025-11-21) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [This weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025)[Nov 21 - Nov 23](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025)[Nov 28 - Nov 30](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) ### Popular places to visit #### Woods Island Commune with nature and explore the great outdoors at Woods Island during your travels in Woolford. [](https://expedia.ca/Woods-Island-Maryland.d924439555136950272.Vacation-Attraction) ## Cities near Woolford ![Cambridge](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/253000/253345-Cambridge-Easternshore.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Cambridge [](https://expedia.ca/Cambridge.dx6608) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [4 Star Hotels in Algonquin](https://www.expedia.ca/4Star-Algonquin-Hotels.s40-0-d553248635975860123.Travel-Guide-Filter-Hotels) - [Farmstay in Algonquin](https://www.expedia.ca/Algonquin-Agritourism.d553248635975860123-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Algonquin](https://www.expedia.ca/Algonquin-Apart-Hotels.d553248635975860123-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Algonquin](https://www.expedia.ca/Algonquin-Bed-And-Breakfast.d553248635975860123-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Algonquin](https://www.expedia.ca/Algonquin-Guest-Houses.d553248635975860123-aaGuestHouses.Travel-Guide-Accommodation) - 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