Title: Book the Best Chatham Hotels with FREE PARKING 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 Hotels with Free Parking in Chatham, MA from CA $247 ![](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 Hotels with Free Parking Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-13&endDate=2025-10-14&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-14&endDate=2025-10-15&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chatham Hotels with Free Parking ![Front of property](https://images.trvl-media.com/lodging/27000000/26510000/26506800/26506782/40379add.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/27000000/26510000/26506800/26506782/cd0d1e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26510000/26506800/26506782/a578dbd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/27000000/26510000/26506800/26506782/26293cb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winstead Beach Resort Harwich Port 9.2/10 Wonderful (59) "Very nice hotel, staff. Great location for relaxing visit to the mountains. " CA $298 CA $362 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Harwich-Port-Hotels-Winstead-Beach-Resort.h26506782.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/7cf38365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/e981387d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Queen Beds](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/44c4b987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/550a87c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greyfinch Chatham Inn Chatham 8.8/10 Excellent (250) "Wonderful place to stay" CA $200 CA $278 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Highlander-Village-Inn.h7461681.Hotel-Information) ![Beach bar](https://images.trvl-media.com/lodging/1000000/10000/3700/3689/9873e07e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/1000000/10000/3700/3689/994ac272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Round Cove Suite](https://images.trvl-media.com/lodging/1000000/10000/3700/3689/ce420299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3700/3689/d5db7da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wequassett Resort and Golf Club Harwich 9.4/10 Exceptional (240) "Beautiful property!! Excellent service!! Room was amazing!! " CA $454 CA $557 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Harwich-Hotels-Wequassett-Resort-And-Golf-Club.h3689.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/10000000/10000000/9995800/9995791/88db557f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/10000000/10000000/9995800/9995791/02a9dd6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Bedrooms, Ocean View | Property grounds](https://images.trvl-media.com/lodging/10000000/10000000/9995800/9995791/7b55f685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/10000000/10000000/9995800/9995791/55128a7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hawthorne Chatham 9.4/10 Exceptional (193) "Ocean view with short walk to beach and fishing pier." CA $324 CA $370 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Chatham-Hotels-The-Hawthorne.h9995791.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/cb9a8399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/29e47360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/0959237c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/49d2eb2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winstead Inn Harwich 9.4/10 Exceptional (125) "Windstead Inn is a beautiful property!! Management was great, let us check in early and our room was upgraded. Would definitely stay again." CA $235 CA $285 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Harwich-Hotels-Winstead-Inn.h6165614.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/4000000/3800000/3794800/3794781/878d3dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lower Deluxe Two Bedroom Cottage | Private kitchen](https://images.trvl-media.com/lodging/4000000/3800000/3794800/3794781/3e91efe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Upper Deluxe Two Bedroom Cottage | Garden](https://images.trvl-media.com/lodging/4000000/3800000/3794800/3794781/de2c60bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Queen Room by the Pond](https://images.trvl-media.com/lodging/4000000/3800000/3794800/3794781/e8bf76bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pleasant Bay Village Resort Chatham 9.6/10 Exceptional (297) "Beautiful place to stay!" CA $311 CA $356 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Chatham-Hotels-Pleasant-Bay-Village-Resort.h3794781.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/3000000/2040000/2034800/2034734/80bc5926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2040000/2034800/2034734/d50e3e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/3000000/2040000/2034800/2034734/6317bcd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds, Kitchenette | Private kitchenette](https://images.trvl-media.com/lodging/3000000/2040000/2034800/2034734/83403ebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Seafarer Inn Chatham 9.0/10 Wonderful (313) "Great experience " CA $216 CA $247 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Seafarer-Inn.h2034734.Hotel-Information) ![Superior Room, 2 Double Beds, Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/5000000/4620000/4616500/4616460/2260ae8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/5000000/4620000/4616500/4616460/70584570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4620000/4616500/4616460/6225c6ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/5000000/4620000/4616500/4616460/f4f57159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chatham Motel Chatham 9.2/10 Wonderful (631) "Very safe . Cafe Mood great food run by Jamaican family" CA $307 CA $351 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Chatham-Hotels-The-Chatham-Motel.h4616460.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) ![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) ![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" CA $213 CA $300 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, body treatments, aromatherapy](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5695h3900x5y0-3649fa2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/07d625ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/0e2de95d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Bars Inn Chatham 9.2/10 Wonderful (791) "Beautiful property. Great service!" CA $530 CA $637 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.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=2025-10-27&endDate=2025-10-28®ionId=10743&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## Top Chatham Hotel Reviews ![Margaritaville Resort Cape Cod](//images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg) ### Margaritaville Resort Cape Cod 10/10 Excellent "Rooms were recently renovated and very comfortable. We had requested adjoining rooms for my family of five. When we checked in we were told the rooms were adjoining, they were not and we were unable to move to another accommodation that would allow us all to stay together. That was a definite disappointment that we had to split up our family. " [](https://expedia.ca/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ![Hyannis Harbor Hotel](//images.trvl-media.com/lodging/1000000/60000/55000/54945/741b5772_y.jpg) ### Hyannis Harbor Hotel 10/10 Excellent "Super-friendly hotel, v clean & comfy room (great beds). Restaurant full of kind and efficient staff. I’m coming back." [](https://expedia.ca/Hyannis-Hotels-Hyannis-Harbor-Hotel.h54945.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 "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) ![Greyfinch Chatham Inn](//images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/7cf38365_y.jpg) ### Greyfinch Chatham Inn 10/10 Excellent "Wonderful place to stay" [](https://expedia.ca/Chatham-Hotels-Chatham-Highlander-Village-Inn.h7461681.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) ![Chatham Wayside Inn](//images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002_y.jpg) ### Chatham Wayside Inn 10/10 Excellent "Very charming inn. Very clean and close to restaurants and shopping. " [](https://expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.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) ## 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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