Title: Woolford Vacation Packages & Trips 2026 from CA $7,945 | Expedia.ca [Woolford Travel Guide](https://expedia.ca/Woolford.dx553248635975865928)[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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Woolford Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Woolford Vacation Say bye-bye to the stress of planning and hello to a Woolford vacation package. With the finer details organized before you go, you can focus on discovering every inch of this city, starting with Downtown Cambridge, which is good for bars and pubs, culture and cafes. In the mood for a bit of sightseeing? A trip to Woolford wouldn't be complete without checking out [Harriet Tubman Underground Railroad National Historical Park](https://www.expedia.ca/Harriet-Tubman-Underground-Railroad-National-Historical-Park-Maryland.d553248633992438829.Vacation-Attraction), [Spocott Windmill](https://www.expedia.ca/Spocott-Windmill-Cambridge.d553248621532662092.Vacation-Attraction) and other major attractions. Your ideal Woolford vacation is just clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored just for you. ## Top Woolford Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Bay Estate Luxe Waterfront Home w/ Private Pier, Main+guest House, Bay Views](https://images.trvl-media.com/lodging/101000000/100730000/100728000/100727959/3cc0fc52_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bay Estate Luxe Waterfront Home w/ Private Pier, Main+guest House, Bay Views CA $7,945 per person Feb 21 - Feb 28 found 4 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Salisbury (SBY) No reviews ## Ready to book your vacation to Woolford? Choose your dates ## Woolford Hotel Deals ![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 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=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=95854099&PinnedHotelID=95854099&HadPinnedHotel=true®ionId=553248635975865928) [](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=95854099&PinnedHotelID=95854099&HadPinnedHotel=true®ionId=553248635975865928) ![ 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 9.8/10 Exceptional! (58 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.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=33549150&PinnedHotelID=33549150&HadPinnedHotel=true®ionId=553248635975865928) [](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%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 Fully refundableReserve now, pay when you stay CA $208 CA $369 total Jan 1 - Jan 2, 2026 includes taxes & fees 8.6/10 Excellent! (1,002 reviews) Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience. Reviewed on Dec 5, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=890486&PinnedHotelID=890486&HadPinnedHotel=true®ionId=553248635975865928) [See all 523 properties in Woolford](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=18%2F12%2F2025&endDate=19%2F12%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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](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. Scan the QR code with your device camera and download our app