Title: Book the Best Chatham WINERY Hotels in 2026 | 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://images.trvl-media.com/place/10743/d3f8b886-55a4-46b3-afab-39fd14b1b518.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Chatham, MA from CA $167 - ![](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 [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chatham hotels with winery ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/0ed95706.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) ![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 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) Chatham 9.2/10 Wonderful (602) "Super cozy and clean with fantastic staff and great location loved everyday spent here " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) noushin [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![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) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/f8355c29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/203d6415.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 [](https://www.expedia.ca/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.Hotel-Information) Chatham 9.6/10 Exceptional (101) "Our second year in a row staying here. Cute house and great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin M. CA $123 CA $559 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.Hotel-Information) ![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/c5925a50.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/56000000/55590000/55584200/55584101/0a75a95f.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 [](https://www.expedia.ca/Chatham-Hotels-Beautiful.h55584101.Hotel-Information) Chatham 8.6/10 Excellent (26) "This was a very nice place to stay, the location was perfect. A short walk to town and centrally located on the Cape as a whole. This home had all of the amenities need for a comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey A. CA $276 CA $724 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Chatham-Hotels-Beautiful.h55584101.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/056f2544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/6ac8a051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Voyager Escape King Elite](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/c366b6b8.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) ### Uncommoner Hotel by Reverie Boutique Collection [](https://www.expedia.ca/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) West Yarmouth 9.4/10 Exceptional (97) "Hotel was quiet and very clean , pool water was cool" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robyn CA $146 CA $167 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/ae47522f.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) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/03e2796f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/023eb077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Village Inn Cape Cod [](https://www.expedia.ca/Yarmouth-Port-Hotels-The-Village-Inn-Cape-Cod.h12426891.Hotel-Information) Yarmouth Port 10/10 Exceptional (222) "It was so charming, would definitely stay there again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle CA $233 CA $266 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Yarmouth-Port-Hotels-The-Village-Inn-Cape-Cod.h12426891.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/2000000/1190000/1181400/1181333/cf5e1161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1190000/1181400/1181333/ef31cc2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1190000/1181400/1181333/082cb655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, white sand](https://images.trvl-media.com/lodging/2000000/1190000/1181400/1181333/cf9e4214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Veranda Cape Cod Family Resort [](https://www.expedia.ca/South-Yarmouth-Hotels-Veranda-Cape-Cod-Family-Resort.h1181333.Hotel-Information) Bass River 9.2/10 Wonderful (262) "Beautiful grounds, quiet and comfortable. Very well run. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benita CA $247 CA $282 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/South-Yarmouth-Hotels-Veranda-Cape-Cod-Family-Resort.h1181333.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/c5192e69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/a7d1d86a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, Netflix, books](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/1fed40da.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) ### Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail [](https://www.expedia.ca/Brewster-Hotels-Cheery-House-Wdeck.h72434954.Hotel-Information) West Brewster 9.6/10 Exceptional (50) "House was perfect for our family reunion! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregg H. CA $182 CA $712 total includes taxes & fees Dec 14 - Dec 15 [](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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/f2fbf262.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 [](https://www.expedia.ca/South-Wellfleet-Hotels-Spectacular-Private-Waterfront-Cottage-On-Bayside-Panoramic-Views-Pet-Friendly.h22960042.Hotel-Information) Wellfleet 10/10 Exceptional (75) "Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janice H. CA $192 CA $597 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/South-Wellfleet-Hotels-Spectacular-Private-Waterfront-Cottage-On-Bayside-Panoramic-Views-Pet-Friendly.h22960042.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/ec7f5979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/3bdd02f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/6d5b6832.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/7b4a3afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Beach & Pond Getaway; Heart of Cape Cod [](https://www.expedia.ca/South-Yarmouth-Hotels-Homey-Central-Vacay-W-Game-Room-Near-Beach-And-Pond.h76664195.Hotel-Information) South Yarmouth 10/10 Exceptional (12) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin B. CA $216 CA $753 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/South-Yarmouth-Hotels-Homey-Central-Vacay-W-Game-Room-Near-Beach-And-Pond.h76664195.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/31cd0145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/246e9a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/961738aa.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 [](https://www.expedia.ca/Dennis-Port-Hotels-Quaint-Condo-Near-Private-Beach-Access-With-Fireplace-Close-To-Dining.h75523575.Hotel-Information) Dennis Port 9.0/10 Wonderful (62) "Clean, beautiful, great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer B. CA $83 CA $427 total includes taxes & fees Dec 14 - Dec 15 [](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=2025-12-27&endDate=2025-12-28®ionId=10743&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chatham Hotel Reviews ![Bayside Resort Hotel](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/85f07916_y.jpg) ### Bayside Resort Hotel 10/10 Excellent "everything" [](https://expedia.ca/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information) ![Hyannis Travel Inn](https://images.trvl-media.com/lodging/2000000/1380000/1379200/1379109/fe11d49f_y.jpg) ### Hyannis Travel Inn 10/10 Excellent "Very kind staff. Functional, clean room. Had an early bus and they let me take a few things for breakfast the night before." [](https://expedia.ca/Hyannis-Hotels-Hyannis-Travel-Inn.h1379109.Hotel-Information) ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg) ### Margaritaville Resort Cape Cod 10/10 Excellent "The entire place was spotless and rooom beet pleasant. Staff was super friendly and the Landshark Bar was excellent. Highly recommend a stay here ! " [](https://expedia.ca/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ![Cape Sands Inn](https://images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/aa954682_y.jpg) ### Cape Sands Inn 10/10 Excellent "Clean room, great rate easy checkin and easy checkout. Will stay again. " [](https://expedia.ca/West-Yarmouth-Hotels-Cape-Sands-Inn.h1330174.Hotel-Information) ![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Great accommodation and staff." 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