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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Princess Anne, MD from CA $141 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](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 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-10-24&endDate=2025-10-26&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) ![Direct Bay Front Double Queen Suite - Bayfront | View from room](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/e9bbde17.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) ### Comfort Suites Chincoteague Island Bayfront Resort Downtown Chincoteague 9.6/10 Exceptional (1005) "Very clean & right on the water! Would definitely stay again if in the area! " CA $160 CA $181 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/37b6becc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Pineapple)](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/38798564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/7004874c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/a57ab64b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gillis Grier Bed & Breakfast Salisbury 10/10 Exceptional (158) "An absolute gem of a stay. I will definitely be back! A perfect stop for an affordable and nice stay on your way to beach the next day!" CA $189 CA $212 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Salisbury-Hotels-Gillis-Grier-Bed-And-Breakfast.h42378873.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/w3837h2556x3y4-92e5a8c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Salisbury Plaza Salisbury 6.4/10 (865) "Staff super friendly and rooms are spacious. " CA $126 CA $141 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Salisbury-Hotels-Best-Western-Salisbury-Plaza.h24345.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) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/90860000/90856000/90855993/4e5a34ec.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, offices](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 (30) "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 $184 CA $479 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Salisbury-Hotels-Salisbury-Cottage.h90855993.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) ![Exterior](https://images.trvl-media.com/lodging/97000000/96850000/96846600/96846554/8822f789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/97000000/96850000/96846600/96846554/34b1589b.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) ### 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 $174 CA $466 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Salisbury-Hotels-Salisbury-Hideaway.h96846554.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=2025-10-27&endDate=2025-10-28®ionId=148385&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Princess Anne Hotel Reviews ## 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) - [Hotels with a Pool in Bivalve](https://www.expedia.ca/Bivalve-Hotels-Hotel-With-Pool.0-0-d553248635975846907-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels near Cypress Park](https://www.expedia.ca/Cypress-Park-Hotels.0-l6293998-0.Travel-Guide-Filter-Hotels) - 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