Title: Woolford Travel Guide: Best of Woolford, Maryland Travel 2025 | Expedia.co.uk [Hotels in Woolford](https://expedia.co.uk/Woolford-Hotels.d553248635975865928.Travel-Guide-Hotels)[Holiday Rentals in Woolford](https://expedia.co.uk/Woolford-Holiday-Rentals.d553248635975865928.Travel-Guide-HolidayRentals)[Woolford Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Woolford.d553248635975865928.Car-Hire-Guide)[Woolford Holidays](https://expedia.co.uk/Woolford.d553248635975865928.Holidays-City-Breaks) # Woolford Travel Guide ## Tourist Guide ## Visit Woolford Things to do - Top hotels in Woolford - Top Holiday 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 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! (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 24 Aug 2025 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=33549150&PinnedHotelID=33549150&HadPinnedHotel=true®ionId=553248635975865928) [](https://expedia.co.uk/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%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 holiday home in Woolford. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad ... 9.4/10 Exceptional! (20 reviews) Family vacation The home was spacious and clean. We appreciated the comfortable beds and linens.The kitchen is well stocked and functions well.Simply and nicely decorated.We looked forward to kayaking and enjoyed that, but,it is quite mushy getting down and into the water. We went to all the recommended locations ... Reviewed on 7 Aug 2025 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=95854099&PinnedHotelID=95854099&HadPinnedHotel=true®ionId=553248635975865928) [](https://expedia.co.uk/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%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 £159 23 Nov - 24 Nov includes taxes & fees Stay at this 4-star 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 ... 8.6/10 Excellent! (1,000 reviews) The room was spotless. The staff were courteous and helpful. Fantastic hotel! Reviewed on 28 Oct 2025 [](https://expedia.co.uk/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=890486&PinnedHotelID=890486&HadPinnedHotel=true®ionId=553248635975865928) [See all 516 properties in Woolford](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=10%2F11%2F2025&endDate=11%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. ![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 holiday home in Woolford. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad ... 9.4/10 Exceptional! (20 reviews) Family vacation The home was spacious and clean. We appreciated the comfortable beds and linens.The kitchen is well stocked and functions well.Simply and nicely decorated.We looked forward to kayaking and enjoyed that, but,it is quite mushy getting down and into the water. We went to all the recommended locations ... Reviewed on 7 Aug 2025 [](https://expedia.co.uk/Woolford-Hotels-The-Blue-Heron-Spacious-Waterfront-Eastern-Shore-Getaway-With-Kayaks.h95854099.Hotel-Information) ![ 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 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! (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 24 Aug 2025 [](https://expedia.co.uk/Woolford-Hotels-Newer-Luxury-Waterfront-Beach.h33549150.Hotel-Information) ![Waterfront Solomons Apartment](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977749/w506h683x258y0-cd0997d8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront Solomons Apartment Solomons, MD Stay at this family-friendly apartment in Solomons. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions J.C. Lore Oyster House and Solomons ... 9/10 Wonderful! (13 reviews) The place was very cute and love the location. Owner and maintenance were very responsive to my needs. It was pretty clean for the most part, other than afew things left in trash in bathroom. Dryer didn’t work. Small things, but overall great stay!! Would stay again! Reviewed on 14 Oct 2025 [](https://expedia.co.uk/Solomons-Hotels-Waterfront-Solomons-Apartment.h109977749.Hotel-Information) [See all properties in Woolford](https://expedia.co.uk/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.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-09&endDate=2025-11-10) [Tonight](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-09&endDate=2025-11-10) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-09&endDate=2025-11-10) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-09&endDate=2025-11-10)[9 Nov - 10 Nov](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-09&endDate=2025-11-10) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-10&endDate=2025-11-11) [Tomorrow night](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-10&endDate=2025-11-11) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-10&endDate=2025-11-11) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-10&endDate=2025-11-11)[10 Nov - 11 Nov](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-11-10&endDate=2025-11-11) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [Next weekend](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025)[14 Nov - 16 Nov](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=14%2F11%2F2025&endDate=16%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.co.uk/Woods-Island-Maryland.d924439555136950272.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.co.uk/Cambridge.dx6608) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - [4 Star Hotels in Hoopers Island](https://www.expedia.co.uk/4Star-Hoopers-Island-Hotels.s40-0-d553248635976006636.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Cambridge](https://www.expedia.co.uk/5Star-Cambridge-Hotels.s50-0-d6608.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Royal Oak](https://www.expedia.co.uk/5Star-Royal-Oak-Hotels.s50-0-d6047042.Travel-Guide-Filter-Hotels) - [Algonquin Hotels](https://www.expedia.co.uk/Algonquin-Hotels.d553248635975860123.Travel-Guide-Hotels) - [Hotels near Blackwater National Wildlife Refuge](https://www.expedia.co.uk/Blackwater-National-Wildlife-Refuge-Hotels.0-l6340491-0.Travel-Guide-Filter-Hotels) - 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[Visit Fishing Creek](https://www.expedia.co.uk/Fishing-Creek.dx3000440577) - [Visit Great Mills](https://www.expedia.co.uk/Great-Mills.dx3000347893) - [Harriet Tubman Birthplace Marker](https://www.expedia.co.uk/Harriet-Tubman-Birthplace-Marker-Cambridge.d553248621561879377.Attraction) - [Visit Hoopers Island](https://www.expedia.co.uk/Hoopers-Island.dx553248635976006636) - [Visit Hurlock](https://www.expedia.co.uk/Hurlock.dx3000440672) - [Visit Kent Island](https://www.expedia.co.uk/Kent-Island.dx553248635077608788) - [Visit Lexington Park](https://www.expedia.co.uk/Lexington-Park.dx8609) - [Visit Lothian](https://www.expedia.co.uk/Lothian.dx3000440697) - [Visit Lusby](https://www.expedia.co.uk/Lusby.dx6359190) - [Visit Maryland](https://www.expedia.co.uk/Maryland.dx222) - [Visit Oxford](https://www.expedia.co.uk/Oxford.dx142793) - [Visit Piney Point](https://www.expedia.co.uk/Piney-Point.dx6141117) - [Visit Port Republic](https://www.expedia.co.uk/Port-Republic.dx3000440823) - [Visit Prince Frederick](https://www.expedia.co.uk/Prince-Frederick.dx500577) - [Richardson Maritime Museum](https://www.expedia.co.uk/Richardson-Maritime-Museum-Downtown-Cambridge.d553248621532662094.Attraction) - [Visit Rose Haven](https://www.expedia.co.uk/Rose-Haven.dx153066) - [Royal Oak Holidays](https://www.expedia.co.uk/Royal-Oak.d6047042.Holidays-City-Breaks) - [Visit Scotland](https://www.expedia.co.uk/Scotland.dx68298) - [Visit Shady Side](https://www.expedia.co.uk/Shady-Side.dx6264943) - [Visit Southern Maryland](https://www.expedia.co.uk/Southern-Maryland.dx6057463) - [Spocott Windmill](https://www.expedia.co.uk/Spocott-Windmill-Cambridge.d553248621532662092.Attraction) - [Visit St. George Island](https://www.expedia.co.uk/St-George-Island.dx6338431) - [Visit St. Leonard](https://www.expedia.co.uk/St-Leonard.dx6340492) - [Visit St. Michaels](https://www.expedia.co.uk/St-Michaels.dx5940) - [Visit Westover](https://www.expedia.co.uk/Westover.dx6355110) - [Car hire Oxford](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Oxford.d142793.Car-Hire-Guide) - 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