Title: Chatham Vacation Packages & Trips 2026 from CA $1,285 | 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 Boston Hotel](https://images.trvl-media.com/lodging/101000000/100140000/100136300/100136229/54a79fec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Boston Hotel Brighton CA $1,285 per person May 22 - May 28 found 12 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Boston (BOS) 7.4/10 Good! (849 reviews) Clean room, adequate breakfast, friendly staff. Free parking. Only issue was it took a long time for the shower water to get hot. Good budget option in an are where few exist. Reviewed on Mar 4, 2026 ![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 $1,933 per person May 8 - May 11 found 1 day ago Roundtrip non-stop flight included Halifax (YHZ) to Boston (BOS) 9.8/10 Exceptional! (1,001 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 ![DoubleTree Suites by Hilton Hotel Boston - Cambridge](https://images.trvl-media.com/lodging/1000000/10000/1000/946/2356f482_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree Suites by Hilton Hotel Boston - Cambridge Allston CA $1,847 per person May 22 - May 28 found 12 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Boston (BOS) 9/10 Wonderful! (1,007 reviews) Good stay I will go again. The only issue was that one of the towels had a hair on it. Reviewed on Mar 2, 2026 ![Eurostars The Boxer](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/ee935931_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars The Boxer West End CA $2,368 per person Apr 18 - Apr 22 found 19 hours ago Roundtrip non-stop flight included Halifax (YHZ) to Boston (BOS) 8.6/10 Excellent! (1,384 reviews) Good location to T.D. Garden. Reviewed on Mar 7, 2026 ![Fairmont Copley Plaza, Boston](https://images.trvl-media.com/lodging/1000000/30000/26000/25981/9ccd9e02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Copley Plaza, Boston Back Bay CA $1,869 per person May 22 - May 28 found 12 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Boston (BOS) 9/10 Wonderful! (1,186 reviews) Very relaxing hotel Nice & elegant Reviewed on Mar 7, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_10743) ### 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/1000000/20000/19200/19139/13fe4b58_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chatham Bars Inn 297 Shore Rd Chatham MA CA $499 CA $571 total Mar 9 - Mar 10 includes taxes & fees [](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%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! (638 reviews) We booked the Hotel, called to check on the room as there was a Power outage in the area due to snow. We were told on the phone the room was ready. We arrived, went to check in. The women a reception informed us "You know we have no electricity, hot water, all facilities were closed. They were were ... Reviewed on Mar 3, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=1517204&PinnedHotelID=1517204&HadPinnedHotel=true®ionId=10743) [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=1517204&PinnedHotelID=1517204&HadPinnedHotel=true®ionId=10743) ![Captain's House Inn](https://images.trvl-media.com/lodging/3000000/2830000/2824300/2824230/450bb45e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Captain's House Inn 369 Old Harbor Road Chatham MA 9.8/10 Exceptional! (215 reviews) Great place to stay in Chatham. Went for First Night celebrations and the Inn was clean and comfortable and served one of the best breakfasts! Highly recommend! Reviewed on Jan 3, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=2824230&PinnedHotelID=2824230&HadPinnedHotel=true®ionId=10743) [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=2824230&PinnedHotelID=2824230&HadPinnedHotel=true®ionId=10743) [See all 4,801 properties in Chatham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F03%2F2026&endDate=10%2F03%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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