Title: Book the Best Brewster WINERY Hotels in 2025 | Expedia.ca [Brewster Travel Guide](https://expedia.ca/Brewster.dx9069)[Hotels in Brewster](https://expedia.ca/Brewster-Hotels.d9069.Travel-Guide-Hotels)[Vacation Rentals in Brewster](https://expedia.ca/Brewster-Vacation-Rentals.d9069.Travel-Guide-VacationRentals)[Flights to Brewster](https://expedia.ca/Cheap-Flights-To-Brewster.d9069.Travel-Guide-Flights)[Brewster Car Rentals](https://expedia.ca/Car-Rentals-In-Brewster.d9069.Car-Rental-Guide)[Brewster Vacation Packages](https://expedia.ca/Brewster.d9069.Destination-Travel-Guides) ![Brewster which includes a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105439-Brewster.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Brewster, MA from CA $184 ![](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 Brewster Winery Hotels Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=9069&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=9069&startDate=2025-10-26&endDate=2025-10-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=9069&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9069&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Brewster Winery Hotels ![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) ![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/c100b426.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) "Clean, lots of space, great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenna M. B. CA $185 CA $729 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Brewster-Hotels-Cheery-House-Wdeck.h72434954.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.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) ![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) ### Chatham Wayside Inn Chatham 9.2/10 Wonderful (577) "Great hotel, great locatiion" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $213 CA $300 total includes taxes & fees Oct 27 - Oct 28 [](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) ![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) ![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) ### Uncommoner Hotel by Reverie Boutique Collection West Yarmouth 9.2/10 Wonderful (80) "Great staff, beautiful property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $165 CA $189 total includes taxes & fees Oct 26 - Oct 27 [](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) ![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) ![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) ### The Village Inn Cape Cod Yarmouth Port 10/10 Exceptional (221) "It was so charming, would definitely stay there again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle CA $237 CA $271 total includes taxes & fees Nov 10 - Nov 11 [](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) ![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) ![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) ### 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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike D. CA $124 CA $573 total includes taxes & fees Oct 28 - Oct 29 [](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) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038675/c6c65d48.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) ![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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin R. CA $92 CA $367 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/North-Truro-Hotels-Seaside-Studio-With-Amazing-Water-Views-Private-Beach-Access-Across-The-Street.h90038675.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/8200/8135/53ed8649.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/8200/8135/1b122287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 King Bed, Golf View | View from room](https://images.trvl-media.com/lodging/1000000/10000/8200/8135/1d638eab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8200/8135/e89b1ba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cape Cod Irish Village Hyannis 6.4/10 (1007) "We go on a September Cape cod golf trip every year and always stay at the Irish village. Great prices, food, and entertainment. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $160 CA $184 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Hyannis-Hotels-Resort-Conference-Center-At-Hyannis.h8135.Hotel-Information) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/67000000/66050000/66041900/66041897/21403ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/67000000/66050000/66041900/66041897/2c8e6b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/67000000/66050000/66041900/66041897/ad1ac2ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/67000000/66050000/66041900/66041897/ea549ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy, Ground-Floor Getaway w/ Free WiFi, a Kitchen, Shared Pool, & Private Patio North Truro 8.4/10 Very good (24) "Great accommodations! Great location! Right on the shuttle bus route so you can be downtown Ptown in minutes!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanne B. CA $112 CA $388 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/North-Truro-Hotels-Cozy.h66041897.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) ![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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/f2f728e1.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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janice H. CA $278 CA $714 total includes taxes & fees Nov 10 - Nov 11 [](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) ![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/eadc4fbf.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) ![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 (59) "Loved our stay in Dennis. The condo was so nice and so clean.. I would certainly consider next summer to revisit. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosemarie P. CA $84 CA $401 total includes taxes & fees Oct 28 - Oct 29 [](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=2025-11-08&endDate=2025-11-09®ionId=9069&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Brewster Hotel Reviews ![Hyannis Harbor Hotel](//images.trvl-media.com/lodging/1000000/60000/55000/54945/741b5772_y.jpg) ### Hyannis Harbor Hotel 10/10 Excellent "Close to the hospital and absolutely clean ! " [](https://expedia.ca/Hyannis-Hotels-Hyannis-Harbor-Hotel.h54945.Hotel-Information) ![Cape Sands Inn](//images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/aa954682_y.jpg) ### Cape Sands Inn 10/10 Excellent "Clean room nice view" [](https://expedia.ca/West-Yarmouth-Hotels-Cape-Sands-Inn.h1330174.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 "Amazing hotel! So well-equipped and beautifully decorated, clean and new. Would 100% stay here again! " [](https://expedia.ca/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) ![Hyannis Travel Inn](//images.trvl-media.com/lodging/2000000/1380000/1379200/1379109/fe11d49f_y.jpg) ### Hyannis Travel Inn 10/10 Excellent "The hotel staff was great! Friendly and helpful. Really near the dock to catch the ferry to Nantucket. " [](https://expedia.ca/Hyannis-Hotels-Hyannis-Travel-Inn.h1379109.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 "Resort was everything we wanted." [](https://expedia.ca/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ![Hyannis Plaza Hotel](//images.trvl-media.com/lodging/2000000/1120000/1119300/1119277/f7fc1d07_y.jpg) ### Hyannis Plaza Hotel 10/10 Excellent "Thank you, was good experience. Will stay again and will advise your hotel to my friend and family. " [](https://expedia.ca/Hyannis-Hotels-Hyannis-Plaza-Hotel.h1119277.Hotel-Information) ![Bayside Resort Hotel](//images.trvl-media.com/lodging/1000000/900000/896700/896697/85f07916_y.jpg) ### Bayside Resort Hotel 10/10 Excellent "The hotel is great all the staff are amazing from the guys and the great ladies at the front desk, the breakfast and the cleaning. Love to come here." [](https://expedia.ca/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.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 "Everything was comfortable, very nice front desk person " [](https://expedia.ca/Eastham-Hotels-Captains-Quarters-Motel-Conference-Center.h1080509.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 "Excellent stay." 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