Title: Book the Best East Orleans WINERY Hotels in 2025 | Expedia.ca [East Orleans Travel Guide](https://expedia.ca/Orleans-East-Orleans.dx99564)[Vacation Rentals in Orleans](https://expedia.ca/Orleans-Vacation-Rentals.d142149.Travel-Guide-VacationRentals)[Flights to Orleans](https://expedia.ca/Cheap-Flights-To-Orleans.d142149.Travel-Guide-Flights)[Things to do in Orleans](https://expedia.ca/Things-To-Do-In-Orleans.d142149.Travel-Guide-Activities)[East Orleans Car Rentals](https://expedia.ca/Car-Rentals-In-East-Orleans.d99564.Car-Rental-Guide)[East Orleans Vacations](https://expedia.ca/East-Orleans.d99564.Destination-Travel-Guides) ![Nauset Beach featuring a sandy beach as well as a couple](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105873-Nauset-Beach.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in East Orleans, MA from CA $194 ![](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 East Orleans Winery Hotels Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=99564&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=99564&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=99564&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=99564&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top East Orleans Winery Hotels ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/f436a6d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/471fd6ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/9874775f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Wayside Inn Chatham 9.2/10 Wonderful (574) "Great hotel, great locatiion" CA $214 CA $301 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/15000000/14770000/14763200/14763138/6ed01d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/15000000/14770000/14763200/14763138/86a55b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace Apartment | In-room dining](https://images.trvl-media.com/lodging/15000000/14770000/14763200/14763138/6635c198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/15000000/14770000/14763200/14763138/b28b2f57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kingfisher Harwich Port Harwich Port 9.0/10 Wonderful (35) "We had a wonderful stay ! The room was clean, comfortable, and well-maintained — everything we needed for a relax stay! " CA $315 CA $361 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Harwich-Port-Hotels-Seadar-Inn-By-The-Sea.h14763138.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/76dbfadf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![VISIONARY KING ELITE](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/82541975.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/ff5be5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/75730e05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Uncommoner Hotel by Reverie Boutique Collection West Yarmouth 9.2/10 Wonderful (71) "Such a nice place to stay for a weekend getaway, we will definitely be back!" CA $170 CA $194 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/00d26354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/2b1f0d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/c14b1773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/1c660188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Village Inn Cape Cod Yarmouth Port 10/10 Exceptional (221) "Jennifer is a wonderful host! Breakfast on the back porch was delicious and a great start to the day. Rooms are comfortable and the back of the house where we were was, is quiet. Highly recommend. " CA $237 CA $272 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Yarmouth-Port-Hotels-The-Village-Inn-Cape-Cod.h12426891.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/bab152c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/d9225b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/9355f506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/49d1d00f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK Chatham 9.6/10 Exceptional (99) "Stayed here for a weekend with my fiance and our dog and it was perfect. Short 5 minute drive from downtown and all the great restaurants and shopping. Very dog friendly with fenced in backyard. " CA $125 CA $577 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038675/b577e840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038675/90e23c15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038675/6f47b868.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038675/c15b9de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seaside studio with amazing water views & private beach access across the street Truro 8.0/10 Very good (5) "Cute little space with great views and convenient location." CA $84 CA $360 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/North-Truro-Hotels-Seaside-Studio-With-Amazing-Water-Views-Private-Beach-Access-Across-The-Street.h90038675.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/8928d372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, Netflix, books](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/c100b426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free internet, bed sheets](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/3e9866f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, Netflix, books](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/a58600d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail West Brewster 9.6/10 Exceptional (50) "Enjoyed the stay at the house very much. The house was as described and very clean. Great location and we plan on staying again in the future." CA $185 CA $728 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Brewster-Hotels-Cheery-House-Wdeck.h72434954.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/abe7cc3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/43937c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/01e797f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/180-2a992e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly Wellfleet 10/10 Exceptional (74) "Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed." CA $316 CA $756 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/South-Wellfleet-Hotels-Spectacular-Private-Waterfront-Cottage-On-Bayside-Panoramic-Views-Pet-Friendly.h22960042.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/77bb82da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/89d3eb8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/eadc4fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/9f0abd42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint condo near private beach access with fireplace - close to dining Dennis Port 9.0/10 Wonderful (57) "Loved our stay in Dennis. The condo was so nice and so clean.. I would certainly consider next summer to revisit. " CA $84 CA $399 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Dennis-Port-Hotels-Quaint-Condo-Near-Private-Beach-Access-With-Fireplace-Close-To-Dining.h75523575.Hotel-Information) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/0a75a95f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/60d936ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/59c7a7ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/9f2630b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham Chatham 8.6/10 Excellent (26) "Our family took our first vacation as a family of 3 and the house was perfect!" CA $281 CA $746 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Chatham-Hotels-Beautiful.h55584101.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=2025-10-31&endDate=2025-11-01®ionId=99564&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top East Orleans Hotel Reviews ![Hyannis Travel Inn](//images.trvl-media.com/lodging/2000000/1380000/1379200/1379109/fe11d49f_y.jpg) ### Hyannis Travel Inn 10/10 Excellent "My friends and I had a great stay clean environment, pleasant staff at front desk and cleaners were very accommodating. Love the pool/hot tub as well. " [](https://expedia.ca/Hyannis-Hotels-Hyannis-Travel-Inn.h1379109.Hotel-Information) ![Anchor In Distinctive Waterfront Lodging](//images.trvl-media.com/lodging/8000000/7650000/7640900/7640889/7438dff7_y.jpg) ### Anchor In Distinctive Waterfront Lodging 10/10 Excellent "Big room but small bathroom" [](https://expedia.ca/Hyannis-Hotels-Anchor-In-Distinctive-Waterfront-Lodging.h7640889.Hotel-Information) ![Hampton Inn & Suites Cape Cod-West Yarmouth](//images.trvl-media.com/lodging/3000000/2560000/2558700/2558618/dc2c7156_y.jpg) ### Hampton Inn & Suites Cape Cod-West Yarmouth 10/10 Excellent "Overall, this was a wonderful stay from start to finish. I would absolutely return and recommend it to anyone looking for a relaxing, high-quality hotel experience — and seriously, don’t miss the breakfast lots of choice. From the moment I arrived, the staff were welcoming, attentive, and genuinely helpful — it set the tone for a great stay. Used the laundry facilities too they were good" [](https://expedia.ca/West-Yarmouth-Hotels-Hampton-Inn-Suites-Cape-Cod-West-Yarmouth.h2558618.Hotel-Information) ![Chatham Bars Inn](//images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Excellent experience all around Gorgeous location and beautiful hotel Lively lobby " [](https://expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ![Bayside Resort Hotel](//images.trvl-media.com/lodging/1000000/900000/896700/896697/85f07916_y.jpg) ### Bayside Resort Hotel 10/10 Excellent "Amazing all around " [](https://expedia.ca/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information) ![Hyannis Harbor Hotel](//images.trvl-media.com/lodging/1000000/60000/55000/54945/741b5772_y.jpg) ### Hyannis Harbor Hotel 10/10 Excellent "Super-friendly hotel, v clean & comfy room (great beds). Restaurant full of kind and efficient staff. I’m coming back." [](https://expedia.ca/Hyannis-Hotels-Hyannis-Harbor-Hotel.h54945.Hotel-Information) ![Uncommoner Hotel by Reverie Boutique Collection](//images.trvl-media.com/lodging/1000000/490000/480800/480770/76dbfadf_y.jpg) ### Uncommoner Hotel by Reverie Boutique Collection 10/10 Excellent "Hotel was renovation this year, yes, room is clean and stylish. Also provide everyday room cleaning service. Staffs are so friendly. Parking is easy and feel safe. The location is excellent, walking distance go eating and shopping, vary restaurants are nearby. Will back again. " [](https://expedia.ca/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) ![Captains Quarters Motel & Conference Center](//images.trvl-media.com/lodging/2000000/1090000/1080600/1080509/7b4bf26e_y.jpg) ### Captains Quarters Motel & Conference Center 10/10 Excellent "Tracy is wonderful, the housekeepers are great, we love captain quarters" [](https://expedia.ca/Eastham-Hotels-Captains-Quarters-Motel-Conference-Center.h1080509.Hotel-Information) ![Cape Sands Inn](//images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/aa954682_y.jpg) ### Cape Sands Inn 10/10 Excellent "OK" [](https://expedia.ca/West-Yarmouth-Hotels-Cape-Sands-Inn.h1330174.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [1 Star Hotels in Orleans](https://www.expedia.ca/1Star-Orleans-Hotels.s10-0-d142149.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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[Visit Orleans](https://www.expedia.ca/Orleans.dx142149) - [Car rental Orleans](https://www.expedia.ca/Car-Rentals-In-Orleans.d142149.Car-Rental-Guide) - [Orleans Vacation Rentals](https://www.expedia.ca/Orleans-Vacation-Rentals.d142149.Travel-Guide-VacationRentals) - [Book Hotels in East Orleans on Expedia.com](https://www.expedia.com/East-Orleans-Orleans-Hotels-Winery-Hotel.0-n99564-0-tWineryHotel.Travel-Guide-Filter-Hotels)