Title: Book the Best Eastham WINERY Hotels in 2025 | Expedia.ca [Eastham Travel Guide](https://expedia.ca/Eastham.dx10844)[Hotels in Eastham](https://expedia.ca/Eastham-Hotels.d10844.Travel-Guide-Hotels)[Vacation Rentals in Eastham](https://expedia.ca/Eastham-Vacation-Rentals.d10844.Travel-Guide-VacationRentals)[Flights to Eastham](https://expedia.ca/Cheap-Flights-To-Eastham.d10844.Travel-Guide-Flights)[Eastham Car Rentals](https://expedia.ca/Car-Rentals-In-Eastham.d10844.Car-Rental-Guide)[Eastham Vacation Packages](https://expedia.ca/Eastham.d10844.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105484-Eastham.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Eastham, MA from CA $188 ![](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 Eastham Winery Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=10844&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=10844&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=10844&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=10844&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Eastham 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) ![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) ![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 (571) "Great hotel, great locatiion" [](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) ![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) ![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) ### 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) ![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 (66) "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) ![Private beach](https://images.trvl-media.com/lodging/11000000/10390000/10388800/10388795/36a192b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/11000000/10390000/10388800/10388795/0d1e52a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Refrigerator, Beachfront](https://images.trvl-media.com/lodging/11000000/10390000/10388800/10388795/98ad913d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10390000/10388800/10388795/2061092d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Sea Motor Inn North Truro 8.4/10 Very good (1002) "Decent room for the price." CA $164 CA $188 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/North-Truro-Hotels-Blue-Sea-Motor-Inn.h10388795.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) ![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) ![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) ### 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) ![Beach nearby](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038675/b577e840.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) ![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) ### 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 $358 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/North-Truro-Hotels-Seaside-Studio-With-Amazing-Water-Views-Private-Beach-Access-Across-The-Street.h90038675.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) ![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) ![Garden](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/6a955bb4.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) ![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) ![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) ### 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) ![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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/89d3eb8c.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) ![Smart TV](https://images.trvl-media.com/lodging/116000000/115550000/115546000/115545914/a83d5a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/116000000/115550000/115546000/115545914/bdbdfe6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115550000/115546000/115545914/7d5db133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/116000000/115550000/115546000/115545914/71759a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom apartment in fabulous Provincetown Provincetown 10/10 Exceptional (2) CA $119 CA $256 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Provincetown-Hotels-Charming-1-Bedroom-Apartment-In-Fabulous-Provincetown.h115545914.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=10844&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Eastham 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) ![The Inn at the Oaks](//images.trvl-media.com/lodging/2000000/1510000/1505000/1504936/3bd960cd_y.jpg) ### The Inn at the Oaks 10/10 Excellent "Delightful and well situated." 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[North Eastham Hotels](https://www.expedia.ca/North-Eastham-Hotels.d6131864.Travel-Guide-Hotels) - [Adults Only Resorts & in Orleans](https://www.expedia.ca/Orleans-Hotels-Adults-Only-Resorts.0-0-d142149-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Orleans](https://www.expedia.ca/Orleans-Hotels-Beach-Hotel.0-0-d142149-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Orleans](https://www.expedia.ca/Orleans-Hotels-Boutique-Hotel.0-0-d142149-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Orleans](https://www.expedia.ca/Orleans-Hotels-Casino-Hotel.0-0-d142149-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Orleans](https://www.expedia.ca/Orleans-Hotels-Cheap-Hotels.0-0-d142149-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Orleans](https://www.expedia.ca/Orleans-Hotels-Family-Hotel.0-0-d142149-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Orleans](https://www.expedia.ca/Orleans-Hotels-Golf-Hotel.0-0-d142149-tGolfHotel.Travel-Guide-Filter-Hotels) - 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[Golf Hotels in Salem](https://www.expedia.ca/Salem-Hotels-Golf-Hotel.0-0-d6600-tGolfHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Salem](https://www.expedia.ca/Salem-Hotels-Honeymoon-Hotels.0-0-d6600-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Salem](https://www.expedia.ca/Salem-Hotels-Hotels-With-Bar.0-0-d6600-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Salem](https://www.expedia.ca/Salem-Hotels-Mountain-Hotels.0-0-d6600-tMountainHotels.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Salem](https://www.expedia.ca/Salem-Hotels-Waterpark-Hotels.0-0-d6600-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Salem](https://www.expedia.ca/Salem-Hotels-Winery-Hotel.0-0-d6600-tWineryHotel.Travel-Guide-Filter-Hotels) - [Edward Penniman House and Barn](https://www.expedia.ca/Edward-Penniman-House-And-Barn-Eastham.d6286871.Vacation-Attraction) - [Nauset Beach](https://www.expedia.ca/Nauset-Beach-Massachusetts.d6070191.Vacation-Attraction) - [Nauset Light Beach](https://www.expedia.ca/Nauset-Light-Beach-Eastham.d6070193.Vacation-Attraction) - [Visit North Eastham](https://www.expedia.ca/North-Eastham.dx6131864) - [Book Winery Hotels in Eastham on Expedia.com](https://www.expedia.com/Eastham-Hotels-Winery-Hotel.0-0-d10844-tWineryHotel.Travel-Guide-Filter-Hotels)