Title: Visit Woolford: 2026 Travel Guide for Woolford, Maryland | Expedia.com [Hotels in Woolford](https://expedia.com/Woolford-Hotels.d553248635975865928.Travel-Guide-Hotels)[Vacation Rentals in Woolford](https://expedia.com/Woolford-Vacation-Rentals.d553248635975865928.Travel-Guide-VacationRentals)[Car Rentals in Woolford](https://expedia.com/Car-Rentals-In-Woolford.d553248635975865928.Car-Rental-Guide)[Woolford Vacation Packages](https://expedia.com/Woolford.d553248635975865928.Destination-Travel-Guides) # Woolford, MD ## Travel Guide ![Birds - Cattle Egret, Blackwater National Wildlife Refuge, Virginia](https://images.trvl-media.com/place/553248635975865928/dbd6d7b0-c9d1-4118-b96f-516a26296cfd.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Woolford Things to do - Woolford Hotel Deals - Vacation Rentals in Woolford ![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 ... 9.6/10 Exceptional! (28 reviews) The house was spacious and comfortable, a great fit for our work trip. Reviewed on Mar 2, 2026 [Get rates](https://expedia.com/Hotel-Search?startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&selected=95854099&PinnedHotelID=95854099&HadPinnedHotel=true®ionId=553248635975865928) [](https://expedia.com/Hotel-Search?startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&selected=95854099&PinnedHotelID=95854099&HadPinnedHotel=true®ionId=553248635975865928) ![ Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/5273b469_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted 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! (75 reviews) The home is in a stunning location, and was perfect for our family gathering over the Thanksgiving holiday. Everything you need for a relaxing, enjoyable getaway is provided in this home, and we’d absolutely stay there again! Reviewed on Dec 1, 2025 [Get rates](https://expedia.com/Hotel-Search?startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&selected=33549150&PinnedHotelID=33549150&HadPinnedHotel=true®ionId=553248635975865928) [](https://expedia.com/Hotel-Search?startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&selected=33549150&PinnedHotelID=33549150&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 $245 nightly $278 total Mar 29 - Mar 30 Total with taxes and 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. ... 8.8/10 Excellent! (1,001 reviews) Friendly and helpful staff, pleasant and comfortable room, good food, convenient location and wonderful scenery. Reviewed on Mar 20, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=890486&PinnedHotelID=890486&HadPinnedHotel=true®ionId=553248635975865928) [See all 523 properties in Woolford](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F27%2F2026&endDate=3%2F28%2F2026®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. !["Endless Summer" Waterfront on the Chesapeake Bay!](https://images.trvl-media.com/lodging/110000000/109370000/109364900/109364811/8b55faca_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### "Endless Summer" Waterfront on the Chesapeake Bay! Woolford MD Stay at this vacation home in Woolford. Enjoy private pools, laundry facilities, and patios. Popular attractions Ragged Island and Spocott Windmill are located ... 10/10 Exceptional! (6 reviews) We had a great visit at “Endless Summer “. Everything was as advertised. House, pool and property were great. Enjoyed seeing eagles on the dock in the mornings. Communication with the host was timely and helpful. Reviewed on Dec 30, 2025 [](https://expedia.com/Woolford-Hotels-Endless-Summer-Waterfront-On-The-Chesapeake-Bay.h109364811.Hotel-Information) ![ Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/5273b469_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted 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! (75 reviews) The home is in a stunning location, and was perfect for our family gathering over the Thanksgiving holiday. Everything you need for a relaxing, enjoyable getaway is provided in this home, and we’d absolutely stay there again! Reviewed on Dec 1, 2025 [](https://expedia.com/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 ... 9.6/10 Exceptional! (28 reviews) The house was spacious and comfortable, a great fit for our work trip. Reviewed on Mar 2, 2026 [](https://expedia.com/Woolford-Hotels-The-Blue-Heron-Spacious-Waterfront-Eastern-Shore-Getaway-With-Kayaks.h95854099.Hotel-Information) [See all properties in Woolford](https://expedia.com/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 [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2026-03-26&endDate=2026-03-27)[Mar 26 - Mar 27](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2026-03-26&endDate=2026-03-27) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2026-03-27&endDate=2026-03-28)[Mar 27 - Mar 28](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2026-03-27&endDate=2026-03-28) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)[Mar 27 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026) ### Popular places to visit #### Woods Island Commune with nature and explore the great outdoors at Woods Island during your travels in Woolford. [](https://expedia.com/Woods-Island-Maryland.d924439555136950272.Vacation-Attraction) ## Cities near Woolford ![Cambridge](https://images.trvl-media.com/place/6608/8ce19001-5246-4d03-a239-330291c6972a.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Cambridge - Cities near Woolford - Places of interest [Cambridge](https://expedia.com/Cambridge.dx6608)[Church Creek](https://expedia.com/Church-Creek.dx89567) - [Chesapeake Bay ](https://expedia.com/Chesapeake-Bay-United-States-of-America.d6056980.Vacation-Attraction) - [Patuxent River Naval Air Station ](https://expedia.com/Patuxent-River-Naval-Air-Station-Lexington-Park.d553248621561074007.Vacation-Attraction) - [Blackwater National Wildlife Refuge ](https://expedia.com/Blackwater-National-Wildlife-Refuge-Maryland.d6340491.Vacation-Attraction) - [Calvert Cliffs State Park ](https://expedia.com/Calvert-Cliffs-State-Park-Lusby.d553248621532662085.Vacation-Attraction) - [Chesapeake Bay Maritime Museum ](https://expedia.com/Chesapeake-Bay-Maritime-Museum-Downtown-St-Michaels.d553248633992441010.Vacation-Attraction) - [Breezy Point Beach ](https://expedia.com/Breezy-Point-Beach-Chesapeake-Beach.d553248621532662089.Vacation-Attraction) - [St. Michaels Winery ](https://expedia.com/St-Michaels-Winery-Downtown-St-Michaels.d553248633992438808.Vacation-Attraction) - [Harriet Tubman Underground Railroad National Historical Park ](https://expedia.com/Harriet-Tubman-Underground-Railroad-National-Historical-Park-Madison.d553248633992438829.Vacation-Attraction) - [Gerry Boyle Park at Great Marsh ](https://expedia.com/Gerry-Boyle-Park-At-Great-Marsh-Cambridge.d6286137.Vacation-Attraction) - [Northern Chesapeake Bay ](https://expedia.com/Northern-Chesapeake-Bay-Maryland.d6051456.Vacation-Attraction) - [Avalon Theatre ](https://expedia.com/Avalon-Theatre-Easton.d6286426.Vacation-Attraction) - [Cove Point Lighthouse ](https://expedia.com/Cove-Point-Lighthouse-Lusby.d553248621561879362.Vacation-Attraction) - [Jefferson Patterson Park and Museum ](https://expedia.com/Jefferson-Patterson-Park-And-Museum-St-Leonard.d553248621532662081.Vacation-Attraction) - [Choptank River Lighthouse ](https://expedia.com/Choptank-River-Lighthouse-Cambridge.d6286144.Vacation-Attraction) - [Dorchester County Visitors Center ](https://expedia.com/Dorchester-County-Visitors-Center-Cambridge.d553248621561879598.Vacation-Attraction) - [Harriet Tubman Museum and Educational Center ](https://expedia.com/Harriet-Tubman-Museum-And-Educational-Center-Downtown-Cambridge.d553248621532662095.Vacation-Attraction) - [Long Wharf Park ](https://expedia.com/Long-Wharf-Park-Cambridge.d6286116.Vacation-Attraction) - [Bill Burton Fishing Pier State Park ](https://expedia.com/Bill-Burton-Fishing-Pier-State-Park-Trappe.d553248633992438879.Vacation-Attraction) - [Layton's Chance Vineyard and Winery ](https://expedia.com/Laytons-Chance-Vineyard-And-Winery-Vienna.d553248621532662322.Vacation-Attraction) - [Bruce Gabrielson's Surf Art Gallery and Museum ](https://expedia.com/Bruce-Gabrielsons-Surf-Art-Gallery-And-Museum-Chesapeake-Beach.d553248621532662090.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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