Title: Chatham Vacation Packages & Trips 2026 from CA $1,091 | 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. ![Hyatt Regency Boston/Cambridge](https://images.trvl-media.com/lodging/1000000/20000/16100/16079/944dfde2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Boston/Cambridge MIT CA $1,091 per person Apr 8 - Apr 13 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Boston (BOS) 9/10 Wonderful! (2,215 reviews) Convenient and clean. Love the glass atrium and the views of the Charles River. Reviewed on Jan 16, 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 $2,122 per person Mar 28 - Apr 2 found 21 hours ago Roundtrip flight included Edmonton (YEG) to Boston (BOS) 9.8/10 Exceptional! (1,005 reviews) Amazing stay in Boston. The staff is extremely friendly and helpful, the rooms are updated and clean, the health club was top of the line, and the location is very convenient to a lot of our favorite places in Boston. Reviewed on Jan 20, 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 $2,653 per person Apr 8 - Apr 13 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Boston (BOS) 9.6/10 Exceptional! (181 reviews) I had a blast at Raffles Reviewed on Jan 12, 2026 ![Hilton Boston Back Bay](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Boston Back Bay Fenway–Kenmore CA $1,299 per person Mar 28 - Apr 2 found 22 hours ago Roundtrip flight included Edmonton (YEG) to Boston (BOS) 8.6/10 Excellent! (1,229 reviews) Room is amazing I love how room service even fold our pajama. Impeccable into details. They sent a microwave to our room as per request. I hope they have Hot Water ready in lobby 24/7\. Access to that is very limited Reviewed on Jan 20, 2026 ![The Newbury Boston](https://images.trvl-media.com/lodging/1000000/10000/400/395/de8ba46e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Newbury Boston Back Bay CA $2,114 per person Mar 28 - Apr 2 found 22 hours ago Roundtrip flight included Edmonton (YEG) to Boston (BOS) 9.4/10 Exceptional! (536 reviews) Staff was friendly and flexible ! Rooms were spacious and beautiful, the housekeeping was not as clean or organized or detailed as other places I’ve been to but still good Reviewed on Jan 4, 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 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 CA $163 CA $247 total Jan 22 - Jan 23 includes taxes & fees 9.2/10 Wonderful! (621 reviews) Nice, comfortable room and clean bathroom. Friendly staff, especially Elena at the bar. Great location - very walkable area and beautiful, even in the winter. Reviewed on Jan 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F01%2F2026&endDate=23%2F01%2F2026&selected=1517204&PinnedHotelID=1517204&HadPinnedHotel=true®ionId=10743) ![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 $504 CA $576 total Jan 22 - Jan 23 includes taxes & fees 9/10 Wonderful! (804 reviews) Room was very clean but a little dated also there is very little space to put your clothes away…no dressers Reviewed on Jan 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F01%2F2026&endDate=23%2F01%2F2026&selected=19139&PinnedHotelID=19139&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=04%2F02%2F2026&endDate=05%2F02%2F2026&selected=15581826&PinnedHotelID=15581826&HadPinnedHotel=true®ionId=10743) [](https://expedia.ca/Hotel-Search?startDate=04%2F02%2F2026&endDate=05%2F02%2F2026&selected=15581826&PinnedHotelID=15581826&HadPinnedHotel=true®ionId=10743) [See all 4,757 properties in Chatham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=22%2F01%2F2026&endDate=23%2F01%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 #### 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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