Title: Book the Best Chatham WINERY Hotels in 2025 | Expedia.ca [Chatham Travel Guide](https://expedia.ca/Chatham.dx10743)[Hotels in Chatham](https://expedia.ca/Chatham-Hotels.d10743.Travel-Guide-Hotels)[Vacation Rentals in Chatham](https://expedia.ca/Chatham-Vacation-Rentals.d10743.Travel-Guide-VacationRentals)[Flights to Chatham](https://expedia.ca/Cheap-Flights-To-Chatham.d10743.Travel-Guide-Flights)[Chatham Car Rentals](https://expedia.ca/Car-Rentals-In-Chatham.d10743.Car-Rental-Guide)[Chatham Vacation Packages](https://expedia.ca/Chatham.d10743.Destination-Travel-Guides) ![Chatham featuring a windmill, general coastal views and wild flowers](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105460-Chatham.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Chatham, 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 Chatham Winery Hotels Tonight [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chatham 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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/e74c9a7c.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) ![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) ### Chatham Wayside Inn Chatham 9.2/10 Wonderful (571) "Great hotel, great locatiion" [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.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 $572 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.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) ![Outdoor dining](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/59c7a7ef.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) ![TV, books](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/97bd2b9b.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 $280 CA $739 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Chatham-Hotels-Beautiful.h55584101.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) ![Terrace Apartment | View from room](https://images.trvl-media.com/lodging/15000000/14770000/14763200/14763138/8a34403c.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 $248 CA $284 total includes taxes & fees Oct 13 - Oct 14 [](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 (65) "Such a nice place to stay for a weekend getaway, we will definitely be back!" CA $169 CA $194 total includes taxes & fees Oct 13 - Oct 14 [](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) ![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) ![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) ### 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 $271 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Yarmouth-Port-Hotels-The-Village-Inn-Cape-Cod.h12426891.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) ![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/c5192e69.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 $730 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Brewster-Hotels-Cheery-House-Wdeck.h72434954.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/c0db5e1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/798d2068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/a7bbdf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/cf7f29f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cape Cod Villa pond front vacation home, retreat, spa, venue, film location Harwich - Brewster Border 10/10 Exceptional (6) "Lovely property with attentive hosts " CA $665 CA $1,369 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Harwich-Hotels-Pond-Front-In-The-Woods.h69397439.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) ![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) ![1 bedroom, internet, bed sheets](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/592ba5e4.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) "The condo was lovely. Super clean. The beach was small and Shelly/rocky but that’s okay. Bathrooms/showers were great! Bed was good. Couch bed was awful unfortunately but I know that’s how to have a good mattress on. We would stay again!!" CA $84 CA $400 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Dennis-Port-Hotels-Quaint-Condo-Near-Private-Beach-Access-With-Fireplace-Close-To-Dining.h75523575.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/43937c74.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 $349 CA $805 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) 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=2025-10-26&endDate=2025-10-27®ionId=10743&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chatham Hotel Reviews ![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) ![Hyannis Travel Inn](//images.trvl-media.com/lodging/2000000/1380000/1379200/1379109/fe11d49f_y.jpg) ### Hyannis Travel Inn 10/10 Excellent "The staff is very friendly and helpful. Highly recommended!" [](https://expedia.ca/Hyannis-Hotels-Hyannis-Travel-Inn.h1379109.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 "Nice place. Clean and comfy bed. " [](https://expedia.ca/West-Yarmouth-Hotels-Hampton-Inn-Suites-Cape-Cod-West-Yarmouth.h2558618.Hotel-Information) ![Hyannis Harbor Hotel](//images.trvl-media.com/lodging/1000000/60000/55000/54945/741b5772_y.jpg) ### Hyannis Harbor Hotel 10/10 Excellent "Execelwl " [](https://expedia.ca/Hyannis-Hotels-Hyannis-Harbor-Hotel.h54945.Hotel-Information) ![Chatham Bars Inn](//images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Wonderful experience " [](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 "Fantastic time" [](https://expedia.ca/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information) ![Hyannis Plaza Hotel](//images.trvl-media.com/lodging/2000000/1120000/1119300/1119277/f7fc1d07_y.jpg) ### Hyannis Plaza Hotel 10/10 Excellent "very clean" [](https://expedia.ca/Hyannis-Hotels-Hyannis-Plaza-Hotel.h1119277.Hotel-Information) ![Margaritaville Resort Cape Cod](//images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg) ### Margaritaville Resort Cape Cod 10/10 Excellent "It was what one would expect!!!" 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