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 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=18%2F10%2F2025&endDate=19%2F10%2F2025&selected=33549150&PinnedHotelID=33549150&HadPinnedHotel=true®ionId=553248635975865928) [](https://expedia.ca/Hotel-Search?startDate=18%2F10%2F2025&endDate=19%2F10%2F2025&selected=33549150&PinnedHotelID=33549150&HadPinnedHotel=true®ionId=553248635975865928) ![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### St Michaels Inn 1228 S Talbot Street, St. Michaels, MD CA $126 CA $139 total Oct 7 - Oct 8 includes taxes & fees Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ... 8/10 Very Good! (1,001 reviews) "Our room was clean but dated. The water had a bad smell to it." Reviewed on Sep 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F10%2F2025&endDate=08%2F10%2F2025&selected=10281&PinnedHotelID=10281&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 CA $267 CA $369 total Oct 5 - Oct 6 includes taxes & fees Stay at this 4-star 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! (1,012 reviews) "Indoor and outdoor pools were very clean and nice" Reviewed on Sep 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F10%2F2025&endDate=06%2F10%2F2025&selected=890486&PinnedHotelID=890486&HadPinnedHotel=true®ionId=553248635975865928) [See all 528 properties in Woolford](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=05%2F10%2F2025&endDate=06%2F10%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 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 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! (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 Aug 7, 2025 [](https://expedia.ca/Woolford-Hotels-The-Blue-Heron-Spacious-Waterfront-Eastern-Shore-Getaway-With-Kayaks.h95854099.Hotel-Information) ![John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/c5bdec51_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels! Saint Michaels Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina ... 9.4/10 Exceptional! (117 reviews) "Beautifully restored historic home, in a quaint neighborhood, near the water and downtown. We loved it!" Reviewed on Sep 21, 2025 [](https://expedia.ca/St-Michaels-Hotels-John-Bruff-Waterview-Cottage-On-Harbor-And-On-Park-In-Town-St-Michaels.h32562385.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=2025-10-04&endDate=2025-10-05) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-10-04&endDate=2025-10-05)[Oct 4 - Oct 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-10-05&endDate=2025-10-06) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-10-05&endDate=2025-10-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-10-05&endDate=2025-10-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-10-05&endDate=2025-10-06)[Oct 5 - Oct 6](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=2025-10-05&endDate=2025-10-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025)[Oct 10 - Oct 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865928&startDate=10%2F10%2F2025&endDate=12%2F10%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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[Visit Solomons](https://www.expedia.ca/Solomons.dx159522) - [Visit Southern Maryland](https://www.expedia.ca/Southern-Maryland.dx6057463) - [Visit St. George Island](https://www.expedia.ca/St-George-Island.dx6338431) - [Visit Taylors Island](https://www.expedia.ca/Taylors-Island.dx3000440924) - [Car rental Cambridge](https://www.expedia.ca/Car-Rentals-In-Cambridge.d6608.Car-Rental-Guide) - [National Car Rental Rental Cars in Cambridge](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Cambridge.d6608-c42.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in Cambridge](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-Cambridge.d6608-c45.Car-Rental-Guide-Suppliers) - Cities near Woolford - Places of interest [Cambridge](https://expedia.ca/Cambridge.dx6608) - [Long Wharf Park](https://expedia.ca/Long-Wharf-Park-Cambridge.d6286116.Vacation-Attraction) - [Bill Burton Fishing Pier State Park](https://expedia.ca/Bill-Burton-Fishing-Pier-State-Park-Trappe.d553248633992438879.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points 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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