Title: Book the Best Princess Anne WINERY Hotels in 2025 | Expedia.ca [Hotels in Princess Anne](https://expedia.ca/Princess-Anne-Hotels.d148385.Travel-Guide-Hotels)[Vacation Rentals in Princess Anne](https://expedia.ca/Princess-Anne-Vacation-Rentals.d148385.Travel-Guide-VacationRentals)[Princess Anne Car Rentals](https://expedia.ca/Car-Rentals-In-Princess-Anne.d148385.Car-Rental-Guide)[Princess Anne Vacation Packages](https://expedia.ca/Princess-Anne.d148385.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/winery.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Princess Anne, MD from CA $125 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Princess Anne Winery Hotels Tonight [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Princess Anne Winery Hotels ![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/e422830e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/e8514eb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fishing](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/0c592b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/86f5de21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Chincoteague Island Bayfront Resort Chincoteague 9.6/10 Exceptional (1001) "Very clean & right on the water! Would definitely stay again if in the area! " CA $159 CA $180 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88410000/88401300/88401206/ec86906c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/89000000/88410000/88401300/88401206/3df7bbe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/89000000/88410000/88401300/88401206/e1fd0374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88410000/88401300/88401206/125a449b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning waterfront panoramic view getaway house Captain's Cove 9.8/10 Exceptional (56) "The Property was very well-maintained and accommodating, with most everything you could need. This made the stay much simpler and more enjoyable. The dock and kayaks were a great addition to the fun. " CA $87 CA $591 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Greenbackville-Hotels-Stunning-Waterfront-Panoramic-View-Getaway-House.h88401206.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/w3840h2556x0y4-a75b7a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/82de6f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/w3837h2556x3y4-92e5a8c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/w3837h2555x3y5-92d39155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Salisbury Plaza Salisbury 6.4/10 (859) "Amazing stay" CA $112 CA $125 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Salisbury-Hotels-Best-Western-Salisbury-Plaza.h24345.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/97000000/96850000/96846600/96846554/2462387a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96850000/96846600/96846554/11b28d7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96850000/96846600/96846554/8822f789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96850000/96846600/96846554/63a15e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salisbury Hideaway Salisbury 10/10 Exceptional (19) "Great house and beautiful neighborhood near downtown Salisbury and the University. House was clean and well-stocked with everything we needed. Really enjoyed our stay!" CA $176 CA $468 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Salisbury-Hotels-Salisbury-Hideaway.h96846554.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90860000/90856000/90855993/w1024h675x0y4-1f95c122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90860000/90856000/90855993/w1024h676x0y3-eba4b48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90860000/90856000/90855993/w1024h676x0y3-ba52558d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/91000000/90860000/90856000/90855993/w1024h675x0y4-18a3b0ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salisbury Cottage Salisbury 10/10 Exceptional (29) "This property was very convenient to everything we needed. It was clean and well equipped and the hosts could not have been nicer or more attentive. We would definitely stay there again. Thank you for a wonderful stay." CA $209 CA $509 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Salisbury-Hotels-Salisbury-Cottage.h90855993.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-17&endDate=2025-10-18®ionId=148385&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Princess Anne Hotel Reviews ![Americas Best Value Inn Princess Anne](//images.trvl-media.com/lodging/1000000/880000/871800/871786/d2fe545c_y.jpg) ### Americas Best Value Inn Princess Anne 10/10 Excellent "Access to other stores " [](https://expedia.ca/Salisbury-Hotels-Americas-Best-Value-Inn-Princess-Anne.h871786.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in Kingston](https://www.expedia.ca/4Star-Kingston-Hotels.s40-0-d553248635975867875.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Baltimore](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - 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