Title: Chatham Vacation Packages & Trips 2026 from CA $1,069 | 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. ![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 $1,069 per person Mar 18 - Mar 24 found 2 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 8.2/10 Very Good! (151 reviews) Room was clean and a good size. Location was perfect - walking distance to where I needed to be. Reviewed on Dec 2, 2025 ![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 $1,490 per person Apr 3 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.8/10 Exceptional! (1,005 reviews) Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem. Reviewed on Jan 25, 2026 ![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 $1,566 per person Mar 12 - Mar 16 found 1 day ago Roundtrip flight included Halifax (YHZ) to Boston (BOS) 9.4/10 Exceptional! (1,003 reviews) Room very well appointed and gym was the stand out Reviewed on Jan 25, 2026 ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/0f66f064_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay CA $2,384 per person Apr 23 - Apr 26 found 1 day ago Roundtrip flight included Halifax (YHZ) to Boston (BOS) 9.6/10 Exceptional! (181 reviews) Everything was great — room was immaculate, hotel was very nice. Would return! Reviewed on Feb 1, 2026 ### Things to do in and around Chatham Chatham, Massachusetts, is perfect for a beach and outdoor vacation, offering scenic views and activities for the whole family. Enjoy golf at local courses, unwind at playgrounds, and partake in tennis programs. Whether you're planning a family holiday or a golf getaway, Chatham's charming beaches and inviting atmosphere make it an ideal destination for relaxation and recreation. **Shopping** In Chatham, visit the Chatham Fish Pier for local seafood vibes and unique finds. For a short drive, check out Rail Trail Bike Shop, just 11.3km away. If you're up for a drive, head to [Atlantic Spice Company](https://www.expedia.ca/Atlantic-Spice-Company-North-Truro.d553248621532666590.Vacation-Attraction), located 40.2km from Chatham, for specialty items. **Recreation** Experience the cultural charm at [Chatham Drama Guild](https://www.expedia.ca/Chatham-Drama-Guild-Chatham.d6311758.Vacation-Attraction), where live performances create unforgettable memories. Enjoy the energetic atmosphere at [Veterans Field](https://www.expedia.ca/Veterans-Field-Chatham.d6070219.Vacation-Attraction), perfect for sports enthusiasts. For a serene outdoor escape, tee off at [Captain's Cove Golf Course](https://www.expedia.ca/Captains-Cove-Golf-Course-Brewster.d6070161.Vacation-Attraction), just 6.4km away, surrounded by picturesque landscapes. **Adventure** Experience thrilling fun at [Orleans Bowling Center](https://www.expedia.ca/Orleans-Bowling-Center-Orleans.d553248621532666579.Vacation-Attraction), an arcadeAdventureZone located 11.3km from Chatham, perfect for family excitement. For adrenaline, head to Bud's Go Karts, also 11.3km away, where you can race against friends. Explore the outdoors at Harwich Herring Run, situated 12.9km from Chatham, and enjoy the natural beauty. **Nightlife** Chatham's nightlife offers a charming coastal vibe. Enjoy fresh seafood and local wines at The Impudent Oyster. For a laid-back evening, visit Chatham Squire for lively music and a friendly atmosphere. Don't miss the stunning sunset views at the beach before heading out for the night. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions near Chatham Chatham, Massachusetts, is a fantastic destination for beach lovers and outdoor enthusiasts alike. Explore its stunning beaches, picturesque golf courses, and charming neighbourhoods. Enjoy a mix of culture and nature on Chatham Island, and don’t hesitate to ask locals any questions you have about the area. With its beautiful scenery and array of activities, Chatham promises a memorable vacation experience. - **[Skaket Beach: ](https://www.expedia.ca/Skaket-Beach-Orleans.d6070215.Vacation-Attraction)** Located 12.9km from Chatham, Skaket Beach offers beautiful sandy shores and stunning sunsets. It's an ideal spot for families looking to enjoy beach vibes, swimming, and beachcombing along the calm waters of Cape Cod Bay. - **[Hardings Lighthouse: ](https://www.expedia.ca/Hardings-Lighthouse-West-Chatham.d6070173.Vacation-Attraction)** Just 3.2km from Chatham, this historic lighthouse is rich in maritime culture. Visitors can marvel at its architecture and enjoy picturesque views of the coastline, making it a perfect spot for history enthusiasts and photographers alike. - **[Cape Cod Museum of Natural History: ](https://www.expedia.ca/Cape-Cod-Museum-Of-Natural-History-West-Brewster.d6070157.Vacation-Attraction)** Situated 14.5km from Chatham, this museum provides a family-friendly experience with engaging exhibits about local ecosystems and wildlife. It's an excellent opportunity to learn and appreciate the natural history of Cape Cod. ### Best time to go to Chatham The best time to visit Chatham is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. February is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 35.6°F (2.0°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | February | 35.4°F (1.9°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | March | 38.5°F (3.6°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | April | 45.3°F (7.4°C) | Light Rain | Mostly Sunny | Average | Average | | May | 53.1°F (11.7°C) | Light Rain | Mostly Sunny | Average | Average | | June | 61.7°F (16.5°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High | | July | 69.6°F (20.9°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High | | August | 70.3°F (21.3°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High | | September | 65.7°F (18.7°C) | Light Rain | Mostly Sunny | Average | Average | | October | 57.9°F (14.4°C) | Light Rain | Mostly Sunny | Moderately Low | Average | | November | 48.6°F (9.2°C) | Light Rain | Mostly Sunny | Moderately Low | Average | | December | 41.5°F (5.3°C) | Light Rain | Mostly Cloudy | Moderately Low | Average | ### Tips to save on your trip to Chatham - Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings. - Consider traveling to Chatham during the low season (January to March) for more affordable options. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ### 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 $498 CA $570 total Feb 12 - Feb 13 includes taxes & fees 9.2/10 Wonderful! (808 reviews) Beautiful property Reviewed on Jan 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&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 Fully refundableReserve now, pay when you stay 9.2/10 Wonderful! (627 reviews) Courteous staff, helpful with dining suggestions. Loved the room. Very comfortable bed, warm and cozy. Reviewed on Jan 29, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=1517204&PinnedHotelID=1517204&HadPinnedHotel=true®ionId=10743) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=1517204&PinnedHotelID=1517204&HadPinnedHotel=true®ionId=10743) ![Surfside Inn Chatham](https://images.trvl-media.com/lodging/16000000/15590000/15581900/15581826/7fbceae0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Surfside Inn Chatham 25 Holway St Chatham MA 8/10 Very Good! (159 reviews) This is a beautiful property very centrally located. I highly recommend the surfside inn. Reviewed on Oct 15, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=15581826&PinnedHotelID=15581826&HadPinnedHotel=true®ionId=10743) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=15581826&PinnedHotelID=15581826&HadPinnedHotel=true®ionId=10743) [See all 4,798 properties in Chatham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®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 ![Summer Baseball Game at Chatham, Cape Cod League](https://images.trvl-media.com/place/6070219/0313a916-3ad0-4cbd-b72f-eb1d6cd99785.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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) #### 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) #### 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. 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[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) - [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) - [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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