Title: Book the Best Annapolis WINERY Hotels in 2026 | Expedia.ca [Annapolis Travel Guide](https://expedia.ca/Annapolis.dx6034082)[Hotels in Annapolis](https://expedia.ca/Annapolis-Hotels.d6034082.Travel-Guide-Hotels)[Vacation Rentals in Annapolis](https://expedia.ca/Annapolis-Vacation-Rentals.d6034082.Travel-Guide-VacationRentals)[Flights to Annapolis](https://expedia.ca/Cheap-Flights-To-Annapolis.d6034082.Travel-Guide-Flights)[Things to do in Annapolis](https://expedia.ca/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities)[Annapolis Car Rentals](https://expedia.ca/Car-Rentals-In-Annapolis.d6034082.Car-Rental-Guide)[Annapolis Vacation Packages](https://expedia.ca/Annapolis.d6034082.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/6034082/a3002046-1aee-4bd3-be34-8475c830687e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Annapolis, MD from CA $104 - ![](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 Annapolis Winery Hotels Tonight [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=6034082&startDate=2025-12-21&endDate=2025-12-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=6034082&startDate=2025-12-22&endDate=2025-12-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6034082&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6034082&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Annapolis hotels with winery ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/b2a36b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/d5668d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8e1aa433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/95f44d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Oasis of Annapolis Star [](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information) Annapolis 10/10 Exceptional (81) "Owners were great hosts. Loved this property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $286 CA $571 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/8a8d7f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/c2958ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/825e8c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/5c5b72be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach [](https://www.expedia.ca/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information) Arundel on the Bay 9.8/10 Exceptional (11) "Great communication with the host, easy check in.. nice property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Henry P. CA $335 CA $741 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/c81ba3f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/0348d35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/733d81ac.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/114000000/113280000/113272300/113272210/85376bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Pet-Friendly Stay - Near Bay & Beaches. [](https://www.expedia.ca/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information) Annapolis 10/10 Exceptional (6) "The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristina CA $324 CA $770 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/4de85be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/081c863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/7e2b4765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2br home w/ parking in downtown Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) Historic District 10/10 Exceptional (72) "Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheldon E. CA $221 CA $500 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Single Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/cbbf2396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) Stevensville 9.2/10 Wonderful (129) "Beautiful and peaceful property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerry CA $197 CA $268 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463441/ff83c83a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463441/73037ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463441/fe70a2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463441/a4aaa0e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Columbia East - Elkridge by IHG [](https://www.expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-Hotel-Suites-Columbia-East-Elkridge.h2463441.Hotel-Information) Elkridge 8.6/10 Excellent (1004) "Clean room, friendly staff, good breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly CA $120 CA $136 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-Hotel-Suites-Columbia-East-Elkridge.h2463441.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/50c62e4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/48533afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/53ebad59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/4366a05e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Baltimore Inner Harbor [](https://www.expedia.ca/Baltimore-Hotels-Hyatt-Regency-Baltimore-Inner-Harbor.h9379.Hotel-Information) Downtown West 8.4/10 Very good (1873) "Clean room and nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marshal CA $175 CA $206 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Baltimore-Hotels-Hyatt-Regency-Baltimore-Inner-Harbor.h9379.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83830000/83828300/83828255/w905h683x59y0-876363d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83830000/83828300/83828255/a6453963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/84000000/83830000/83828300/83828255/w1024h572x0y56-a1edfb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83830000/83828300/83828255/w380h683x322y0-7dc11ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Modern Micro Apt in the Heart of Fells Point! [](https://www.expedia.ca/Baltimore-Hotels-Cozy-Modern-Micro-Apt-In-The-Heart-Of-Fells-Point.h83828255.Hotel-Information) Fells Point 9.0/10 Wonderful (31) "We had such a great stay at the property. Everything was clean and welcoming. It was the perfect little place/space for my wife my 3 yr old son and myself. The street parking in the area was also good. We were able to find a spot right around the corner. The location of the property in relation to a lot of the sites in Fells Point was perfect as well. Everything 5 stars we would definitely recommend and We would definitely book again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan S. CA $143 CA $339 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Baltimore-Hotels-Cozy-Modern-Micro-Apt-In-The-Heart-Of-Fells-Point.h83828255.Hotel-Information) ![Business centre](https://images.trvl-media.com/lodging/2000000/1400000/1397900/1397853/76b8e1c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1400000/1397900/1397853/846b95f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1400000/1397900/1397853/32b1cffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1400000/1397900/1397853/a1842bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn Columbia Gateway [](https://www.expedia.ca/Baltimore-Hotels-Sleep-Inn-Columbia-Gateway.h1397853.Hotel-Information) Jessup 8.2/10 Very good (676) "Nice staff, easy check in process " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrice CA $92 CA $104 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Baltimore-Hotels-Sleep-Inn-Columbia-Gateway.h1397853.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/28400/28314/3a2b6d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/28400/28314/d9fa89ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/30000/28400/28314/9aa828c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/28400/28314/5cebc14d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Revival Baltimore [](https://www.expedia.ca/Baltimore-Hotels-Hotel-Revival-Baltimore.h28314.Hotel-Information) Mount Vernon 9.4/10 Exceptional (1008) "The staff and room were perfect!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $139 CA $182 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Baltimore-Hotels-Hotel-Revival-Baltimore.h28314.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=2026-01-05&endDate=2026-01-06®ionId=6034082&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Annapolis Hotel Reviews ## Frequently asked questions ### How much does a winery hotel in Annapolis cost? ### Which are the top Annapolis winery hotels for couples? > This charming 3-star hotel boasts a fantastic review rating of 9.6, making it an ideal romantic getaway. Nestled near a vineyard, the Inn offers private and public winery tours, allowing couples to explore the local wine scene together. The property features luxurious amenities like Egyptian cotton sheets, designer toiletries, and a fireplace for those cozy evenings. Additionally, you can enjoy a private chef experience and couples dining, ensuring you have a memorable and intimate stay. ### Which area of Annapolis is best to stay in for vineyards and wineries? > For couples seeking a romantic escape, the wineries of Anne Arundel County provide a great backdrop. Imagine enjoying a leisurely afternoon sipping fine wines while taking in the beautiful vineyard landscapes. Many wineries also offer picnic areas, where you can relax together with a bottle of your favourite vintage, creating unforgettable moments. > > > Families will appreciate the educational experiences that local wineries can provide. Many establishments offer family-friendly tours that include insights into the winemaking process, often featuring interactive activities for children. Plus, the serene surroundings make for a lovely day out, allowing you to combine learning with fun. > > > No matter your group's dynamic, staying in Annapolis and venturing into the nearby vineyard region ensures a blend of adventure, relaxation, and quality time spent together. ### Are there hotels in Annapolis near winery tours? > The 3-star Inn at Horn Point, which boasts an impressive rating of 9.6 from our travellers, offers a great experience with vineyard views and options for both private and public winery tours. This hotel features luxurious amenities, including Egyptian cotton sheets, designer toiletries, and even a private chef, making it a lovely choice for a romantic getaway. > > > For a more budget-friendly option, the [Candlewood Suites Annapolis by IHG](https://www.expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) is rated 8.8 and is conveniently located near various winery tour locations. ### What winery activities should we do in Annapolis? > For couples seeking a romantic outing, consider booking a private vineyard tour. Enjoy a leisurely stroll through the vine-laden hills, followed by an intimate tasting session paired with artisanal cheeses. The serene atmosphere and stunning landscapes set a great backdrop for creating cherished memories together. > > > Families will also find plenty to enjoy in Annapolis's winery scene. Many vineyards offer family-friendly events, including outdoor picnics and live music, allowing everyone to unwind and have fun. Some wineries even provide fun activities for kids, ensuring a delightful experience for visitors of all ages. ### Does Annapolis host any wine festivals or events? > For couples seeking a romantic escape, the Chesapeake Bay Wine Festival is another must-attend event. Set amidst picturesque waterfront views, this festival allows couples to sample a variety of wines while enjoying the scenic beauty of the Bay. It's an excellent opportunity for a leisurely day out, complete with gourmet food vendors and artisanal crafts. > > > Families will also find enjoyable experiences in Annapolis, especially at the annual Maryland Wine Festival. This family-friendly event often features activities for children, making it a superb outing for parents looking to introduce their little ones to local culture in a relaxed setting. The festival typically includes live entertainment, arts and crafts, and a variety of food options, ensuring there's something for everyone. ### How can I save on a winery hotel in Annapolis with Expedia? ### Is it cheaper to book flights and a winery hotel in Annapolis as a package deal? ### Can I cancel my winery hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [B&B in Anne Arundel County ](https://www.expedia.ca/Anne-Arundel-County-Bed-And-Breakfast.d553248635083910990-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Anne Arundel County ](https://www.expedia.ca/Anne-Arundel-County-Motels.d553248635083910990-aaMotels.Travel-Guide-Accommodation) - [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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