Title: Book the Best Princess Anne WINERY Hotels in 2026 | 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) ![Aerial view of Princess Anne, Maryland with marshlands and waterways at sunset](https://images.trvl-media.com/place/148385/205c3bf2-4444-43c8-94c9-aefa6641ff7e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/148385/205c3bf2-4444-43c8-94c9-aefa6641ff7e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 3 - Feb 4](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2026-02-03&endDate=2026-02-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 4 - Feb 5](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2026-02-04&endDate=2026-02-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Princess Anne hotels with winery ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/b355d149.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) ![Point of interest](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/0b5ea2de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/17e42883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Chincoteague Island Bayfront Resort [](https://www.expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.Hotel-Information) Downtown Chincoteague 9.6/10 Exceptional (1,001 reviews) "Over all friendly, clean, great continental breakfast and cheerful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim CA $135 CA $153 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/w3836h2556x4y4-1df22480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Accessible, Refrigerator & Microwave](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/w3837h2560x3y0-ad83be30.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/w3837h2557x3y3-45d5f8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Salisbury Plaza [](https://www.expedia.ca/Salisbury-Hotels-Best-Western-Salisbury-Plaza.h24345.Hotel-Information) Salisbury 6.4/10 (897 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence CA $115 CA $128 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Salisbury-Hotels-Best-Western-Salisbury-Plaza.h24345.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/c81cf203.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) ![Interior detail](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/62134013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/215f0904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gillis Grier Bed & Breakfast [](https://www.expedia.ca/Salisbury-Hotels-Gillis-Grier-Bed-And-Breakfast.h42378873.Hotel-Information) Salisbury 10/10 Exceptional (167 reviews) "Great hosts. Terrific breakfast. Very clean. Comfy bed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JoAnn [](https://www.expedia.ca/Salisbury-Hotels-Gillis-Grier-Bed-And-Breakfast.h42378873.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/91000000/90860000/90856000/90855993/eceb0d4d.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) ![Dining](https://images.trvl-media.com/lodging/91000000/90860000/90856000/90855993/w1024h676x0y3-23fa7574.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) ### Salisbury Cottage [](https://www.expedia.ca/Salisbury-Hotels-Salisbury-Cottage.h90855993.Hotel-Information) Salisbury 10/10 Exceptional (34 reviews) "My family and I had a great stay was a comfy and safe space to relax and enjoy our Halloween weekend would definitely recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mackenzie N. CA $161 CA $446 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Salisbury-Hotels-Salisbury-Cottage.h90855993.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) ![Interior](https://images.trvl-media.com/lodging/89000000/88410000/88401300/88401206/ee3a513c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88410000/88401300/88401206/be8de05e.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/dd982d7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities [](https://www.expedia.ca/Greenbackville-Hotels-Stunning-Waterfront-Panoramic-View-Getaway-House.h88401206.Hotel-Information) Captain's Cove 9.8/10 Exceptional (61 reviews) "This is a unique home with beautiful views! The amenities were wonderful, the home was so clean, and Nick was great with checking in to make sure everything was good. Would definitely stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristy C. CA $88 CA $581 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Greenbackville-Hotels-Stunning-Waterfront-Panoramic-View-Getaway-House.h88401206.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96850000/96846600/96846554/f16ec49b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/97000000/96850000/96846600/96846554/811a1e2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/97000000/96850000/96846600/96846554/2462387a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/97000000/96850000/96846600/96846554/ec160e52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salisbury Hideaway [](https://www.expedia.ca/Salisbury-Hotels-Salisbury-Hideaway.h96846554.Hotel-Information) Salisbury 10/10 Exceptional (20 reviews) "This property was wonderful for our trip to Salisbury for my daughter's travel softball tournament. It was only 30-45 minutes from Ocean City (give or take traffic), and very close to many shopping areas and restaurants. The property itself was very clean and provided many necessities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa H. CA $213 CA $511 total includes taxes & fees Mar 5 - Mar 6 [](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=2026-02-17&endDate=2026-02-18®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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