Title: Chatham Vacation Packages & Trips 2025/2026 from CA $909 | 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) ![](https://images.trvl-media.com/place/10743/3f88cd8b-cb5f-4748-8f50-5f2201e66ba3.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chatham Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place #### Your Chatham Vacation Spend less time travel planning and more time having thrilling adventures with a Chatham vacation package. The neighborhood of Harwich Center, which is great for golfing and festivals, makes a great base for your city escape. If your trip to Chatham includes some sightseeing, take in renowned attractions like [Chatham Lighthouse Beach](https://www.expedia.ca/Chatham-Lighthouse-Beach-Massachusetts.d6287419.Vacation-Attraction), [Bank Street Beach](https://www.expedia.ca/Bank-Street-Beach-Harwich-Port.d553248622099865595.Vacation-Attraction) and [Chatham Lighthouse](https://www.expedia.ca/Chatham-Lighthouse-Chatham.d6070163.Vacation-Attraction). Check out Expedia's extensive range of travel options and begin planning your ultimate vacation to Chatham now. ## Top Chatham Vacation Deals Price found within the past 48 hours. Click for updated prices. ![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/66098bc6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Charles Hotel West Cambridge CA $909 per person Nov 7 - Nov 9 found 5 hours ago Roundtrip non-stop flight included Toronto (YTO) to Boston (BOS) 9.4/10 Exceptional! (1,005 reviews) Great location, very friendly staff, clean room. Thanks Sumit. You have a great team. Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-07/2025-11-09/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15861&paandie=true&dealMarker=b3fWbLscUsiTNf0BuuZUcEjBEvoMuD75G4305NyI4cFySugQljviB7d6LjJp2Zih) ![Maverick Suites at 245 Newbury St](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/2e7614de_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Maverick Suites at 245 Newbury St Back Bay CA $1,248 per person Nov 8 - Nov 14 found 18 hours ago Roundtrip flight included Toronto (YTZ) to Boston (BOS) 8.2/10 Very Good! (141 reviews) Clean. Bed super comfortable, easy walk to Fenway, restaurants, subway, shops, library Reviewed on Oct 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-14/?FromAirport=YTZ&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=89756238&paandie=true&dealMarker=4uaJn7mU8PE--MnD35q6RYpQbIp_jUiTfyhxbnXDHkRF9AwEui-IlX2weU-QgC8j) ![Hotel AKA Back Bay](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070718/1a69cacc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel AKA Back Bay Back Bay CA $1,316 per person Dec 28 - Jan 3 found 19 hours ago Roundtrip flight included Montreal (YUL) to Boston (BOS) 9.2/10 Wonderful! (1,150 reviews) The location is very good for proximity to historical sight seeing and many restaurant choices. A short walk to the Arlington MBTA subway station provides a brief ride to Fenway Park. Unfortunately we experienced small bugs in our room. Not sure if they were fleas or some other type of bug. They allow pets to stay at the hotel so it could be related to that. We made management aware and they switched rooms for our last two nights. Our stay was a total of 5-nights, Followup correspondence from hotel management informed us that they had Ecolab come to investigate the room. Ecolab claimed that they did not find any issues. That response puzzled me, as I know that we showed pictures of what we found to the hotel desk staff. Maybe the bugs left the room when we did !?! Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2026-01-03/?FromAirport=YUL&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1070718&paandie=true&dealMarker=HfwB1AGAvqcdZAmr-dp9ELESeNmcWIPkr-UWxw_FXsQIJjy00mn0hOMA2hAuSqbi) ![Maverick Suites at 40 Temple St](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/0dd63623_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Maverick Suites at 40 Temple St Beacon Hill CA $1,074 per person Nov 8 - Nov 14 found 18 hours ago Roundtrip flight included Toronto (YTZ) to Boston (BOS) 7.4/10 Good! (92 reviews) Great small apartment, conveniently located in downtown. The table was rickety and the towels didn't dry out in a single day even though I hung it up. Reviewed on Oct 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-14/?FromAirport=YTZ&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=89660519&paandie=true&dealMarker=4uaJn7mU8PE--MnD35q6RYpQbIp_jUiTfyhxbnXDHkSVsrIFtXJ64XE4d8hWl5J1) ![Maverick Suites at 400 Columbus Ave](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/bf03eabd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Maverick Suites at 400 Columbus Ave South End CA $1,061 per person Nov 8 - Nov 14 found 18 hours ago Roundtrip flight included Toronto (YTZ) to Boston (BOS) 7.4/10 Good! (120 reviews) Property is located in a very nice area. No frill, what they advertise, you get. Reviewed on May 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-14/?FromAirport=YTZ&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=88179829&paandie=true&dealMarker=4uaJn7mU8PE--MnD35q6RYpQbIp_jUiTfyhxbnXDHkT33HcY_3vARYZRTuRMuxfC) ### Chatham Beach Vacation There's nothing that can beat a Chatham vacation. Whether you're indulging in fancy cocktails at a local hot spot or flipping through a book by the shore, your trip to Chatham is the perfect time to live out your beachy dreams. Many travelers will tell you to stay near Ridgevale Beach, located just 3 kilometres from the town center. However, you'll also find a fantastic range of Chatham vacation packages close to Hardings Beach and Cockle Cove Beach, two other well-loved nearby options. ## Ready to book your vacation to Chatham? Choose your dates ## Chatham Hotel Deals ![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chatham Bars Inn 297 Shore Rd, Chatham, MA CA $527 CA $634 total Oct 30 - Oct 31 includes taxes & fees 9/10 Wonderful! (789 reviews) "Beautiful property. Great service!" Reviewed on Sep 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F10%2F2025&endDate=31%2F10%2F2025&selected=19139&PinnedHotelID=19139&HadPinnedHotel=true®ionId=10743) ![Chatham Wayside Inn](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chatham Wayside Inn 512 Main St, Chatham, MA CA $225 CA $313 total Nov 2 - Nov 3 includes taxes & fees 9.2/10 Wonderful! (569 reviews) "A really wonderful spot percolated to explore the cape. A very nice breakfast in the morning!" Reviewed on Oct 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=1517204&PinnedHotelID=1517204&HadPinnedHotel=true®ionId=10743) ![Greyfinch Chatham Inn](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/7cf38365_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Greyfinch Chatham Inn 946 Main Street (Rte 28), Chatham, MA CA $200 CA $276 total Oct 20 - Oct 21 includes taxes & fees 8.8/10 Excellent! (243 reviews) "Clean room and well maintained buildings and pool area" Reviewed on Sep 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=20%2F10%2F2025&endDate=21%2F10%2F2025&selected=7461681&PinnedHotelID=7461681&HadPinnedHotel=true®ionId=10743) [See all 4,627 properties in Chatham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=10743) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Chatham #### Veterans Field Catch an event at Veterans Field during your trip to Chatham. Wander the beautiful beaches and seaside in the area. [](https://expedia.ca/Veterans-Field-Chatham.d6070219.Vacation-Attraction) #### Chatham Drama Guild You can enjoy a show at Chatham Drama Guild during your trip to Chatham. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants. [](https://expedia.ca/Chatham-Drama-Guild-Chatham.d6311758.Vacation-Attraction) #### Monomoy Theatre You can get tickets for a performance at Monomoy Theatre during your trip to Chatham. Wander the beautiful beaches and seaside in the area. [](https://expedia.ca/Monomoy-Theatre-Chatham.d6286898.Vacation-Attraction) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental ### Lodging - [Hotels near Academy of Performing Arts](https://www.expedia.ca/Academy-Of-Performing-Arts-Hotels.0-l553248621532666580-0.Travel-Guide-Filter-Hotels) - [Hotels near Allen Harbor Marina](https://www.expedia.ca/Allen-Harbor-Marina-Hotels.0-l553248622004961370-0.Travel-Guide-Filter-Hotels) - [Hotels near Cape Cod Baseball & Bumper Boats](https://www.expedia.ca/Cape-Cod-Baseball-Bumper-Boats-Hotels.0-l553248621532666557-0.Travel-Guide-Filter-Hotels) - [Hotels near Chatham Fish Pier](https://www.expedia.ca/Chatham-Fish-Pier-Hotels.0-l6286473-0.Travel-Guide-Filter-Hotels) - [Hotels near Chatham Lighthouse Beach](https://www.expedia.ca/Chatham-Lighthouse-Beach-Hotels.0-l6287419-0.Travel-Guide-Filter-Hotels) - [Hotels near Chatham Lighthouse](https://www.expedia.ca/Chatham-Lighthouse-Hotels.0-l6070163-0.Travel-Guide-Filter-Hotels) - 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[Lodges in West Chatham](https://www.expedia.ca/West-Chatham-Lodges.d6285894-aaLodges.Travel-Guide-Accommodation) ### Flights - [Flights to Harwich Port](https://www.expedia.ca/Cheap-Flights-To-Harwich-Port.d113258.Travel-Guide-Flights) ### Packages - [Academy Playhouse](https://www.expedia.ca/Academy-Playhouse-Orleans.d6311794.Vacation-Attraction) - [Bass River Lighthouse](https://www.expedia.ca/Bass-River-Lighthouse-West-Dennis.d6070147.Vacation-Attraction) - [Breakwater Beach](https://www.expedia.ca/Breakwater-Beach-Brewster.d6070149.Vacation-Attraction) - [Brewster Vacations](https://www.expedia.ca/Brewster.d9069.Destination-Travel-Guides) - [Cape Cod Museum of Natural History](https://www.expedia.ca/Cape-Cod-Museum-Of-Natural-History-West-Brewster.d6070157.Vacation-Attraction) - [Cape Cod Vacations](https://www.expedia.ca/Cape-Cod.d180061.Destination-Travel-Guides) - [Captain Bangs Hallet House Museum](https://www.expedia.ca/Captain-Bangs-Hallet-House-Museum-Yarmouth-Port.d6287119.Vacation-Attraction) - [Captain's Cove Golf Course](https://www.expedia.ca/Captains-Cove-Golf-Course-Brewster.d6070161.Vacation-Attraction) - [Chatham Drama Guild](https://www.expedia.ca/Chatham-Drama-Guild-Chatham.d6311758.Vacation-Attraction) - [Dennis Vacations](https://www.expedia.ca/Dennis.d183325.Destination-Travel-Guides) - [Eastham Vacations](https://www.expedia.ca/Eastham.d10844.Destination-Travel-Guides) - [Edward Gorey House](https://www.expedia.ca/Edward-Gorey-House-Yarmouth-Port.d6286501.Vacation-Attraction) - [Edward Penniman House and Barn](https://www.expedia.ca/Edward-Penniman-House-And-Barn-Eastham.d6286871.Vacation-Attraction) - [Hardings Lighthouse](https://www.expedia.ca/Hardings-Lighthouse-West-Chatham.d6070173.Vacation-Attraction) - [Visit Harwich Port](https://www.expedia.ca/Harwich-Port.dx113258) - [Marconi Beach](https://www.expedia.ca/Marconi-Beach-Wellfleet.d6287508.Vacation-Attraction) - [Mayflower Beach](https://www.expedia.ca/Mayflower-Beach-Dennis.d553248621561930301.Vacation-Attraction) - [Monomoy Theatre](https://www.expedia.ca/Monomoy-Theatre-Chatham.d6286898.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 Chatham](https://www.expedia.ca/North-Chatham.dx6285788) - [Orleans Bowling Center](https://www.expedia.ca/Orleans-Bowling-Center-Orleans.d553248621532666579.Vacation-Attraction) - [Orleans Vacations](https://www.expedia.ca/Orleans.d142149.Destination-Travel-Guides) - [Paine's Creek Beach](https://www.expedia.ca/Paines-Creek-Beach-Brewster.d6311778.Vacation-Attraction) - [Ridgevale Beach](https://www.expedia.ca/Ridgevale-Beach-Massachusetts.d6287520.Vacation-Attraction) - [Seagull Beach](https://www.expedia.ca/Seagull-Beach-West-Yarmouth.d6127074.Vacation-Attraction) - [Skaket Beach](https://www.expedia.ca/Skaket-Beach-Orleans.d6070215.Vacation-Attraction) - [Visit South Chatham](https://www.expedia.ca/South-Chatham.dx6285831) - [South Orleans Vacations](https://www.expedia.ca/South-Orleans.d183344.Destination-Travel-Guides) - [Veterans Field](https://www.expedia.ca/Veterans-Field-Chatham.d6070219.Vacation-Attraction) - [West Dennis Beach](https://www.expedia.ca/West-Dennis-Beach-West-Dennis.d6070221.Vacation-Attraction) - [Whydah Pirate Museum](https://www.expedia.ca/Whydah-Pirate-Museum-West-Yarmouth.d553248621533117085.Vacation-Attraction) - [Wilbur Park](https://www.expedia.ca/Wilbur-Park-South-Yarmouth.d6297911.Vacation-Attraction) ### Cars - [Car rentals near Fox Hill](https://www.expedia.ca/Car-Rentals-In-Fox-Hill.d553248621532666570.Car-Rental-Guide) - [Car rental Harwich Port](https://www.expedia.ca/Car-Rentals-In-Harwich-Port.d113258.Car-Rental-Guide) - [Car rental Harwich](https://www.expedia.ca/Car-Rentals-In-Harwich.d183331.Car-Rental-Guide) ### Vacation Rental - [South Chatham Vacation Rentals](https://www.expedia.ca/South-Chatham-Vacation-Rentals.d6285831.Travel-Guide-VacationRentals) \* Savings based on package bookings compared to the price of the same components booked separately. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)