Title: Chatham Vacation Packages & Trips 2025/2026 from CA $710 | 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. ![Lakeside Inn](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/8c770017_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lakeside Inn CA $710 per person Oct 26 - Oct 31 found 19 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 7.4/10 Good! (2,176 reviews) Check in was fast, efficient and polite. Reviewed on Sep 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-26/2025-10-31/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20351&paandie=true&dealMarker=Xu8itrTTLFzwFUDE_GKWiPk8VBF1UYKewrHzYQC8cqKJL8ldHUwsb5Wz1iJ8wsBi) ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/76d84630_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay CA $2,223 per person Dec 16 - Dec 23 found 22 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.8/10 Exceptional! (160 reviews) Best hotel in Boston without question! The staff are exceptional, very friendly and attentive. The masseuses at the spa, especially (I believe her name was) Paula are very skilled and helpful with sore muscles and joints after traveling. La Padrona, Amar, and The Long Bar all have delicious food. I will definitely be back! Reviewed on Sep 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-16/2025-12-23/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=911477&paandie=true&dealMarker=TLeCrVfpSJxzLfqWl9uase4Xe_ab4yISjSRhq13XmHzhHhdGYLZAM8o31myYG8to) ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Harbor Hotel North End CA $1,241 per person Nov 13 - Nov 16 found 1 hour ago Roundtrip non-stop flight included Hamilton (YHM) to Boston (BOS) 9.8/10 Exceptional! (1,008 reviews) The view is great Restaurant is superb Reviewed on Sep 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-13/2025-11-16/?FromAirport=YHM&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=26146&paandie=true&dealMarker=AqebJ43vnqf4x6VQyiaWd9RSlpy1YB9VP_SGpxr99EjMsRfnjgIx5LIqJnPppYNS) ![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 $1,606 per person Oct 27 - Nov 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.4/10 Exceptional! (1,005 reviews) I had a lovely stay at this hotel. Very nice atmosphere and close to many restaurants, shopping, and Harvard campus. Although I did not need parking, there was also an on-premise parking lot. Staff were kind and accommodating. My only issue was that the hotel has shows on the 3rd floor and I could hear the music at night from my room on the 4th FL so beware if you are a light sleeper. Otherwise, I would certainly stay here again when in the Cambridge area. Reviewed on Sep 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-27/2025-11-01/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15861&paandie=true&dealMarker=ONaU62ybbhFVJhN2ny6a24jy6Xw1YbWa8AdBALJ_kDB4DxPnId9jq6ubtn-rod5r) ![Hilton Boston Park Plaza](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/d4a5b47e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Boston Park Plaza Bay Village CA $879 per person Dec 16 - Dec 23 found 22 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 8.4/10 Very Good! (3,154 reviews) The room was really noisy. The cleaning crew were cleaning a room at 8:30 in the evening…. Just wanted to relax after a long day and had to listen to music and a vacuum Reviewed on Sep 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-16/2025-12-23/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4215&paandie=true&dealMarker=TLeCrVfpSJxzLfqWl9uasQypCUzlfRvX3TtYFvOmNzFmHCL-smao2Dn7no24xkDX) ### 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 $537 CA $646 total Oct 13 - Oct 14 includes taxes & fees 9/10 Wonderful! (786 reviews) "Very clean and happy staff" Reviewed on Aug 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%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 $311 CA $412 total Oct 26 - Oct 27 includes taxes & fees 9.2/10 Wonderful! (558 reviews) "Convenient charming and comfortable" Reviewed on Sep 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%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 $224 CA $304 total Oct 20 - Oct 21 includes taxes & fees 8.8/10 Excellent! (242 reviews) Greyfinch, Chatham, September 2025 "We had 5 days at the Greyfinch, rooms and pool area spotless, close to main town to drive just a few minutes. Grocery and chemist were close enough to mark, as was the Mexican and a true diamond called the del-mar. If I had one complaint it was noise from rooms both side, as you could clearly hear ..." Reviewed on Sep 18, 2025 [](https://expedia.ca/Hotel-Search?startDate=20%2F10%2F2025&endDate=21%2F10%2F2025&selected=7461681&PinnedHotelID=7461681&HadPinnedHotel=true®ionId=10743) [See all 4,967 properties in Chatham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F09%2F2025&endDate=27%2F09%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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)