Title: Book the Best Gloucester WINERY Hotels in 2025 | Expedia.ca [Gloucester Travel Guide](https://expedia.ca/Gloucester.dx8008)[Hotels in Gloucester](https://expedia.ca/Gloucester-Hotels.d8008.Travel-Guide-Hotels)[Vacation Rentals in Gloucester](https://expedia.ca/Gloucester-Vacation-Rentals.d8008.Travel-Guide-VacationRentals)[Flights to Gloucester](https://expedia.ca/Cheap-Flights-To-Gloucester.d8008.Travel-Guide-Flights)[Things to do in Gloucester](https://expedia.ca/Things-To-Do-In-Gloucester.d8008.Travel-Guide-Activities)[Gloucester Car Rentals](https://expedia.ca/Car-Rentals-In-Gloucester.d8008.Car-Rental-Guide)[Gloucester Vacation Packages](https://expedia.ca/Gloucester.d8008.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531389-gloucester.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Gloucester, MA from CA $196 ![](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 Gloucester Winery Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=8008&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=8008&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8008&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=8008&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Gloucester Winery Hotels ![Front of property](https://images.trvl-media.com/lodging/90000000/89400000/89399300/89399258/90b2a5a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/90000000/89400000/89399300/89399258/84d00fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![43-inch Smart TV with digital channels, TV, Hulu](https://images.trvl-media.com/lodging/90000000/89400000/89399300/89399258/8b3fa9ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker](https://images.trvl-media.com/lodging/90000000/89400000/89399300/89399258/88b3e715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Beverly Beverly 8.4/10 Very good (358) "Clean room Easy check in. Walkable to Salem Nice hotel overall. Will definitely stay again " CA $196 CA $219 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Boston-Hotels-The-Beverly.h89399258.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/700000/690700/690647/35d4ab15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/700000/690700/690647/5d9bbf95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/700000/690700/690647/1961153a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/700000/690700/690647/d4b92a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Points by Sheraton Boston Logan Airport Revere Revere 8.0/10 Very good (1005) "Lovely little bar, convenient location, happy for shuttle to airport." CA $175 CA $196 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Boston-Hotels-Four-Points-By-Sheraton-Boston-Logan-Airport-Revere.h690647.Hotel-Information) ![Smart TV, stereo](https://images.trvl-media.com/lodging/73000000/72830000/72820900/72820822/da707cc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72830000/72820900/72820822/976a9bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/73000000/72830000/72820900/72820822/269e043d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/73000000/72830000/72820900/72820822/8eb1a17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Breeze -Dog Friendly Cottage Steps 2 Beach Sleeps 6 - 100 yards to Beach! Hampton Beach 9.8/10 Exceptional (24) "Great location. Easy access. Had a wonde Time" CA $209 CA $468 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Hampton-Hotels-Recent-Renovation-1BR-Cottage-New-Furnishings-Modern-Appliances-Steps-To-Beach.h72820822.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/77000000/76680000/76675200/76675161/89db59e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76680000/76675200/76675161/86a63913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/77000000/76680000/76675200/76675161/f6639608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, streaming services](https://images.trvl-media.com/lodging/77000000/76680000/76675200/76675161/c983a9b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront, private balcony, stunning panoramic views of the Atlantic Hampton 9.8/10 Exceptional (45) "We loved the place!!" CA $321 CA $590 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Hampton-Hotels-Shore-To-Please-Oceanfront-With-Stunning-Views-Of-The-Atlantic.h76675161.Hotel-Information) ![Boating](https://images.trvl-media.com/lodging/119000000/118050000/118047500/118047438/267d483e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Non Smoking | Living area](https://images.trvl-media.com/lodging/119000000/118050000/118047500/118047438/7c4bb560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed with Sofa bed, Non Smoking, Kitchenette | Living area](https://images.trvl-media.com/lodging/119000000/118050000/118047500/118047438/aa48bdb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/119000000/118050000/118047500/118047438/03644b3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cutwater Inn & Suites Newburyport 7.4/10 Good (6) "Nice place! We will definitely be back!!!" CA $265 CA $307 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Newburyport-Hotels-Cutwater-Inn-Suites.h118047438.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/58000000/57430000/57427600/57427588/93af1bdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/58000000/57430000/57427600/57427588/w1039h697x0y1-b83aa940.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57430000/57427600/57427588/5c7cbd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/58000000/57430000/57427600/57427588/w1008h701x0y0-06e72e93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront, private balcony with amazing panoramic views of Atlantic Ocean Hampton 9.8/10 Exceptional (47) "Awesome place to be in the summertime." CA $321 CA $587 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Hampton-Hotels-Oceanfront.h57427588.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112080000/112074100/112074082/5ad27856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112080000/112074100/112074082/7835b4f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, DVD player, books](https://images.trvl-media.com/lodging/113000000/112080000/112074100/112074082/47c11369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112080000/112074100/112074082/02929b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes! Hampton Beach 10/10 Exceptional (12) "Family vacation, very short walk to the beach and board walk. Plenty of room for a family to stay. Great back yard for a bbq and relaxing away from the crowds and noise. " CA $378 CA $810 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Hampton-Hotels-Premier.h112074082.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/80000000/79280000/79271800/79271751/ba551416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/80000000/79280000/79271800/79271751/fda2a3e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/80000000/79280000/79271800/79271751/5825c7c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/80000000/79280000/79271800/79271751/b2f90069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront, private porch,unobstructed amazing panoramic views of Atlantic Ocean Hampton Beach 9.4/10 Exceptional (31) "Views and beach access are amazing. Communications with the owners were prompt and clear. The home was clean, comfortable and had everything we needed. Great stay! " CA $840 CA $1,302 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Hampton-Hotels-Sunrise.h79271751.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=2025-10-28&endDate=2025-10-29®ionId=8008&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Gloucester Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Packages - Cars - More ways to book - [Cheap Hotels in Annisquam](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Cheap-Hotels.0-n553248635975257320-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Annisquam](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Historic-Hotel.0-n553248635975257320-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Annisquam](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Honeymoon-Hotels.0-n553248635975257320-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Annisquam](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Pet-Friendly-Hotel.0-n553248635975257320-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Boston](https://www.expedia.ca/Boston-Hotels-Adults-Only-Resorts.0-0-d178239-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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[Luxury Hotels in North Shore](https://www.expedia.ca/North-Shore-Hotels-Luxury-Hotel.0-0-d6047672-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in North Shore](https://www.expedia.ca/North-Shore-Hotels-Oceanfront-Hotels.0-0-d6047672-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Ski Hotels in North Shore](https://www.expedia.ca/North-Shore-Hotels-Ski-Hotel.0-0-d6047672-tSkiHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in North Shore](https://www.expedia.ca/North-Shore-Hotels-Spa-Hotel.0-0-d6047672-tSpaHotel.Travel-Guide-Filter-Hotels) - [North Shore Hotels](https://www.expedia.ca/North-Shore-Hotels.d6047672.Travel-Guide-Hotels) - [Hotels near Northeast Hospital Corporation - Addison Gilbert Campus](https://www.expedia.ca/Northeast-Hospital-Corporation-Addison-Gilbert-Campus-Hotels.0-l553248635997987088-0.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Rockport](https://www.expedia.ca/Rockport-Hotels-Beach-Hotel.0-0-d6350-tBeachHotel.Travel-Guide-Filter-Hotels) - 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[Adults Only Resorts & in Salem](https://www.expedia.ca/Salem-Hotels-Adults-Only-Resorts.0-0-d6600-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Golf Hotels in Salem](https://www.expedia.ca/Salem-Hotels-Golf-Hotel.0-0-d6600-tGolfHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Salem](https://www.expedia.ca/Salem-Hotels-Honeymoon-Hotels.0-0-d6600-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Salem](https://www.expedia.ca/Salem-Hotels-Hotels-With-Bar.0-0-d6600-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Salem](https://www.expedia.ca/Salem-Hotels-Mountain-Hotels.0-0-d6600-tMountainHotels.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Salem](https://www.expedia.ca/Salem-Hotels-Waterpark-Hotels.0-0-d6600-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Salem](https://www.expedia.ca/Salem-Hotels-Winery-Hotel.0-0-d6600-tWineryHotel.Travel-Guide-Filter-Hotels) - [Good Harbor Beach](https://www.expedia.ca/Good-Harbor-Beach-Gloucester.d553248621532667409.Vacation-Attraction) - [Hammond Castle](https://www.expedia.ca/Hammond-Castle-Gloucester.d6092287.Vacation-Attraction) - [North Shore Vacations](https://www.expedia.ca/North-Shore.d6047672.Destination-Travel-Guides) - [Top Rent a Car Rental Cars in North Shore](https://www.expedia.ca/Top-Rent-A-Car-Car-Rentals-In-North-Shore.d6047672-c1028.Car-Rental-Guide-Suppliers) - [Book Winery Hotels in Gloucester on Expedia.com](https://www.expedia.com/Gloucester-Hotels-Winery-Hotel.0-0-d8008-tWineryHotel.Travel-Guide-Filter-Hotels)