Title: South Dennis Vacation Packages & Trips 2026 from CA $1,252 | Expedia.ca [Hotels in South Dennis](https://expedia.ca/South-Dennis-Hotels.d6285885.Travel-Guide-Hotels)[Vacation Rentals in South Dennis](https://expedia.ca/South-Dennis-Vacation-Rentals.d6285885.Travel-Guide-VacationRentals)[South Dennis Car Rentals](https://expedia.ca/Car-Rentals-In-South-Dennis.d6285885.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Dennis 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 South Dennis Vacation Lock in a South Dennis vacation package and get ready for a fantastic adventure. With a reputation for its coastal scenery and family-friendly attractions, there's plenty to love about this city. If your trip to South Dennis includes a little sightseeing, take in popular attractions like [Cape Cod Museum of Art](https://www.expedia.ca/Cape-Cod-Museum-Of-Art-Dennis.d6070155.Vacation-Attraction), [Cape Cod Museum of Natural History](https://www.expedia.ca/Cape-Cod-Museum-Of-Natural-History-West-Brewster.d6070157.Vacation-Attraction) and [Mayflower Beach](https://www.expedia.ca/Mayflower-Beach-Massachusetts.d553248621561930301.Vacation-Attraction). Expedia is here to help you escape the everyday. Tailor your vacation to South Dennis to suit your style of travel, whatever that may look like. ## Top South Dennis Vacation Deals Price found within the past 48 hours. Click for updated prices. ![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 $1,252 per person Apr 3 - Apr 5 found 1 day ago Roundtrip flight included Halifax (YHZ) 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 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 $1,260 per person May 7 - May 12 found 8 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 7.4/10 Good! (802 reviews) Clean room, staff was great, chill and easy to access. Good price as well! Reviewed on Feb 9, 2026 ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Boston Downtown Boston CA $1,326 per person Apr 22 - Apr 25 found 1 day ago Roundtrip non-stop flight included Halifax (YHZ) to Boston (BOS) 9.6/10 Exceptional! (1,004 reviews) Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you Reviewed on Feb 3, 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_6285885) ## Ready to book your vacation to South Dennis? Choose your dates ## South Dennis Hotel Deals ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Margaritaville Resort Cape Cod 1225 Iyannough Rd Hyannis MA Fully refundableReserve now, pay when you stay CA $171 CA $273 total Feb 18 - Feb 19 includes taxes & fees 8.6/10 Excellent! (444 reviews) Clean room, nice staff, the only problem was the internet was slow Reviewed on Feb 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=18%2F02%2F2026&endDate=19%2F02%2F2026&selected=12897&PinnedHotelID=12897&HadPinnedHotel=true®ionId=6285885) ![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 $495 CA $567 total Feb 19 - Feb 20 includes taxes & fees 9.2/10 Wonderful! (808 reviews) Beautiful property Reviewed on Jan 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F02%2F2026&endDate=20%2F02%2F2026&selected=19139&PinnedHotelID=19139&HadPinnedHotel=true®ionId=6285885) ![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! (630 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=28%2F02%2F2026&endDate=01%2F03%2F2026&selected=1517204&PinnedHotelID=1517204&HadPinnedHotel=true®ionId=6285885) [](https://expedia.ca/Hotel-Search?startDate=28%2F02%2F2026&endDate=01%2F03%2F2026&selected=1517204&PinnedHotelID=1517204&HadPinnedHotel=true®ionId=6285885) [See all 5,719 properties in South Dennis](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026®ionId=6285885) 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) ### What to do in South Dennis ![Cape Cod and Provincetown Scenic Self-Guided Driving Audio Tour](https://mediaim.expedia.com/localexpert/47337601/e7340904-330b-4b08-bb24-aa3ac803a21e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour CA $34 per traveller [](https://expedia.ca/things-to-do/cape-cod-provincetown-self-guided-drive-walk-audio-tour.a47337601.activity-details) ![Massachusetts Highlights: Freedom Trail, Salem & More Tour](https://mediaim.expedia.com/localexpert/5247794/991bb3ab-4de4-47da-8b84-5a4e09a0b2d6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours CA $68 per adult [](https://expedia.ca/things-to-do/massachusetts-self-guided-audio-tour-bundle-10-tours.a5247794.activity-details) [See all activities in South Dennis](https://expedia.ca/things-to-do/search?rid=6285885) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app