Title: Woolford Vacation Packages & Trips 2025/2026 from CA $606 | 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

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Better together

Save up to CA $1,096 when you book a flight and hotel together\*

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With over 300,000 hotels worldwide, it's easy to create a perfect package

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#### 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.

![Commander Hotel & Suites](https://images.trvl-media.com/lodging/10000000/9720000/9713100/9713072/0acd7387_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Commander Hotel & Suites

Downtown Ocean City

CA $606

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Salisbury (SBY)

8.6/10 Excellent! (1,006 reviews)

It was safe and convenient. Not quiet but safe and convenient.

Reviewed on Oct 11, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-16/?FromAirport=YOW&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=9713072&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_Oye7gFWJAFQ1vzR0iqPGnlxAKL2CugDEgYMQCevioXeZ)

![Hampton Inn & Suites Ocean City/Bayfront-Convention Center](https://images.trvl-media.com/lodging/6000000/5130000/5121500/5121459/adc9fd46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Midtown Ocean City

CA $635

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Salisbury (SBY)

8.8/10 Excellent! (1,001 reviews)

Nice place and great breakfast options that’s included

Reviewed on Sep 20, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-16/?FromAirport=YOW&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=5121459&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_Oye7gFWJAFQ1vzR0iqPGnlxkK0xn8EgXvys4OEjaFVh5)

![Cambria Hotel Ocean City - Bayfront](https://images.trvl-media.com/lodging/47000000/46190000/46182800/46182729/3b0eebe6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cambria Hotel Ocean City - Bayfront

Downtown Ocean City

CA $649

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Salisbury (SBY)

9.2/10 Wonderful! (1,003 reviews)

Loved my stay here. Staff was friendly and it was clean and safe!

Reviewed on Oct 6, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-16/?FromAirport=YOW&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=46182729&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_Oye7gFWJAFQ1vzR0iqPGnlwNhQPjEPLTvJJ8HWjHmmnL)

![Hilton Ocean City Oceanfront Suites](https://images.trvl-media.com/lodging/1000000/30000/27700/27630/502613d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Ocean City Oceanfront Suites

Midtown Ocean City

CA $718

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Salisbury (SBY)

8.8/10 Excellent! (1,244 reviews)

Room was a nice size. Four adults had plenty of room to navigate throughout the room. The tub was very outdated and not the best to shower in. Can be very difficult for a person who can not step into a deep tub. Staff was very nice and helpful. We did have to wait at the Starbucks line for 15 min since the only employee was in the back and never came back out. The one pool was being cleaned but has a nice vibe. The ocean is just steps away which is amazing. Lots to do in that immediate area. Walking and the use of bus was super easy. Only took the car out once. We would stay there again.

Reviewed on Oct 10, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-16/?FromAirport=YOW&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=27630&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_Oye7gFWJAFQ1vzR0iqPGnlxVeI8R3iCmhMvqnrBHaLfA)

![Holiday Inn & Suites Ocean City by IHG](https://images.trvl-media.com/lodging/1000000/790000/788000/787924/701b41f3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holiday Inn & Suites Ocean City by IHG

Downtown Ocean City

CA $652

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Salisbury (SBY)

9.6/10 Exceptional! (1,212 reviews)

Clean room Very pleasant staff And great food

Reviewed on Oct 11, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-16/?FromAirport=YOW&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=787924&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_Oye7gFWJAFQ1vzR0iqPGnlzUUJ9k6ooNl1etCkJUsWIP)

## Ready to book your vacation to Woolford?

Choose your dates

## Woolford Hotel Deals

![ 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)

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Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Woolford

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=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=33549150&PinnedHotelID=33549150&HadPinnedHotel=true&regionId=553248635975865928)

[](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=33549150&PinnedHotelID=33549150&HadPinnedHotel=true&regionId=553248635975865928)

![Hyatt Regency Chesapeake Bay](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Hyatt Regency Chesapeake Bay

100 Heron Blvd, Cambridge, MD

Fully refundableReserve now, pay when you stay

CA $268

CA $371 total

Oct 13 - Oct 14

includes taxes & fees

8.6/10 Excellent! (1,004 reviews)

"Hyatt regency is more like a Hyatt place … fewer people working , in room dining is in paper boxes with plastic cutlery , but still regency pricing . But excellent pet policy and everyone so kind to pets"

Reviewed on Oct 3, 2025

[](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&selected=890486&PinnedHotelID=890486&HadPinnedHotel=true&regionId=553248635975865928)

![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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St Michaels Inn

1228 S Talbot Street, St. Michaels, MD

Fully refundable

CA $127

CA $140 total

Oct 22 - Oct 23

includes taxes & fees

8/10 Very Good! (1,000 reviews)

"Room was clean, Staff was very friendly and welcoming."

Reviewed on Oct 6, 2025

[](https://expedia.ca/Hotel-Search?startDate=22%2F10%2F2025&endDate=23%2F10%2F2025&selected=10281&PinnedHotelID=10281&HadPinnedHotel=true&regionId=553248635975865928)

[See all 529 properties in Woolford](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&regionId=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.

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All Inclusive Vacations

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Beach Vacations

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Family Vacations

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![](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)

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![QR code to download the app](data:image/png;base64,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)