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) # Find Winery Hotels in Princess Anne, MD from CA $126 - ![](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 [Dec 4 - Dec 5](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-12-04&endDate=2025-12-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 5 - Dec 6](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-12-05&endDate=2025-12-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=148385&startDate=2025-12-12&endDate=2025-12-14&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) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/86f5de21.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) ### Comfort Suites Chincoteague Island Bayfront Resort Downtown Chincoteague 9.6/10 Exceptional (1001) "The staff were wonderful, and the hospitality was amazing. Enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Regina CA $133 CA $151 total includes taxes & fees Dec 10 - Dec 11 [](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) ![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) ![Smart TV, books](https://images.trvl-media.com/lodging/89000000/88410000/88401300/88401206/1046e5bb.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) ### Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities Captain's Cove 9.8/10 Exceptional (59) "Nick is an excellent host. The home was so fun for our family to stay in. The view is so beautiful and peaceful. It is even more beautiful in person. Short drive to reach Chincoteague and Assateague. Stocked with everything you need. I walked down the street and got a massage using the info provided in the house. Thanks for a wonderful and beautiful stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Natalie K. CA $98 CA $606 total includes taxes & fees Dec 5 - Dec 6 [](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/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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/82de6f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Salisbury Plaza Salisbury 6.4/10 (885) "Staff super friendly and rooms are spacious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $113 CA $126 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Salisbury-Hotels-Best-Western-Salisbury-Plaza.h24345.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) ![Staircase](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/7004874c.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) ![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 (165) "They have made my stay feel like I am family " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julia [](https://www.expedia.ca/Salisbury-Hotels-Gillis-Grier-Bed-And-Breakfast.h42378873.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) ![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) ![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) ![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 Salisbury 10/10 Exceptional (33) "Very clean, great communication and fabulous location close to SU!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne M. CA $172 CA $460 total includes taxes & fees Dec 10 - Dec 11 [](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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/97000000/96850000/96846600/96846554/8822f789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salisbury Hideaway Salisbury 10/10 Exceptional (19) "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 $157 CA $441 total includes taxes & fees Dec 8 - Dec 9 [](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=2025-12-18&endDate=2025-12-19®ionId=148385&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Princess Anne Hotel Reviews ![Americas Best Value Inn Princess Anne](https://images.trvl-media.com/lodging/1000000/880000/871800/871786/d2fe545c_y.jpg) ### Americas Best Value Inn Princess Anne 10/10 Excellent "Just passing through and wanted an affordable and comfortable place to spend the night. Clearly an older building, but everything is clean. No complaints!" 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