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 $199 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-02&endDate=2025-10-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-10&endDate=2025-10-12&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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/e74c9a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Wayside Inn Chatham 9.2/10 Wonderful (567) "Great hotel, great locatiion" CA $225 CA $313 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.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) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/10f6fac9.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) ### Uncommoner Hotel by Reverie Boutique Collection West Yarmouth 9.2/10 Wonderful (59) "Such a nice place to stay for a weekend getaway, we will definitely be back!" CA $168 CA $199 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/West-Yarmouth-Hotels-Tidewater-Inn.h480770.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) ![Property amenity](https://images.trvl-media.com/lodging/15000000/14770000/14763200/14763138/b28b2f57.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) ### 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 $247 CA $282 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Harwich-Port-Hotels-Seadar-Inn-By-The-Sea.h14763138.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) ![TV, fireplace, books](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/7e1e24c2.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 (98) "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 $124 CA $561 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.Hotel-Information) ![WhiteCrest, 1 Queen Bed, Kitchenette | Private kitchenette](https://images.trvl-media.com/lodging/15000000/14770000/14768200/14768198/6a213c9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/15000000/14770000/14768200/14768198/3438cbb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/15000000/14770000/14768200/14768198/9d878843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/15000000/14770000/14768200/14768198/f71ecc61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copper Swan Wellfleet 8.0/10 Very good (119) "Brekkies was amazing too. Lovely staff. " [](https://www.expedia.ca/Wellfleet-Hotels-The-Wagner-At-Duck-Creek.h14768198.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) ![TV, books](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/9f2630b8.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) ### 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 $284 CA $744 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Chatham-Hotels-Beautiful.h55584101.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61650000/61643400/61643319/80dc7830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books](https://images.trvl-media.com/lodging/62000000/61650000/61643400/61643319/3e96b60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/62000000/61650000/61643400/61643319/1390ed21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/62000000/61650000/61643400/61643319/c0a86b09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location Dennis Port 9.0/10 Wonderful (24) "Loved the location. Enjoyed breakfasts and lunches in the back and loved the outside shower. So nice to shower off under the stars or sunny sky. Would definitely stay here again" CA $89 CA $472 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Dennis-Port-Hotels-Adorable-Cape-Escape-W-Private-Beach-Access.h61643319.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) "Beautiful property." CA $596 CA $1,285 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Harwich-Hotels-Pond-Front-In-The-Woods.h69397439.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 (49) "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 $184 CA $728 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Brewster-Hotels-Cheery-House-Wdeck.h72434954.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/eadc4fbf.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 $395 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Dennis-Port-Hotels-Quaint-Condo-Near-Private-Beach-Access-With-Fireplace-Close-To-Dining.h75523575.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=2025-10-16&endDate=2025-10-17®ionId=10743&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chatham Hotel Reviews ![Cape Sands Inn](//images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/aa954682_y.jpg) ### Cape Sands Inn 10/10 Excellent "Nice place very clean " [](https://expedia.ca/West-Yarmouth-Hotels-Cape-Sands-Inn.h1330174.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 "Clean and quiet. Good value for the money. " [](https://expedia.ca/Eastham-Hotels-Captains-Quarters-Motel-Conference-Center.h1080509.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 "Everything was perfect " [](https://expedia.ca/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ![Hyannis Travel Inn](//images.trvl-media.com/lodging/2000000/1380000/1379200/1379109/fe11d49f_y.jpg) ### Hyannis Travel Inn 10/10 Excellent "The Room was clean and the staff was excellent." [](https://expedia.ca/Hyannis-Hotels-Hyannis-Travel-Inn.h1379109.Hotel-Information) ![Hyannis Harbor Hotel](//images.trvl-media.com/lodging/1000000/60000/55000/54945/741b5772_y.jpg) ### Hyannis Harbor Hotel 10/10 Excellent "Nice " [](https://expedia.ca/Hyannis-Hotels-Hyannis-Harbor-Hotel.h54945.Hotel-Information) ![Americas Best Value Inn & Suites Hyannis Cape Cod](//images.trvl-media.com/lodging/1000000/920000/913800/913772/b88f545c_y.jpg) ### Americas Best Value Inn & Suites Hyannis Cape Cod 10/10 Excellent "Easy walk to shops and restaurants down town." [](https://expedia.ca/Hyannis-Hotels-Americas-Best-Value-Inn-Suites-Hyannis-Cape-Cod.h913772.Hotel-Information) ![Chatham Bars Inn](//images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Very clean and happy staff" [](https://expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Packages - Cars - More ways to book - [Adults Only Resorts & in Boston](https://www.expedia.ca/Boston-Hotels-Adults-Only-Resorts.0-0-d178239-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Business Hotels in Boston](https://www.expedia.ca/Boston-Hotels-Business-Hotel.0-0-d178239-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Boston](https://www.expedia.ca/Boston-Hotels-Couples-Resorts-Hotels.0-0-d178239-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Boston](https://www.expedia.ca/Boston-Hotels-Golf-Hotel.0-0-d178239-tGolfHotel.Travel-Guide-Filter-Hotels) - 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