Title: South Dennis Vacation Packages & Trips 2026 from CA $942 | 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)

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# South Dennis Vacation Packages

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#### 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.

![The Colonnade Hotel Back Bay](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/f43e7537_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Colonnade Hotel Back Bay

Back Bay

CA $942

per person

Mar 21 - Mar 25

found 24 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9.2/10 Wonderful! (2,268 reviews)

Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..

Reviewed on Feb 2, 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 $2,327

per person

Apr 27 - May 1

found 18 hours 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

![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 $2,939

per person

Apr 29 - May 3

found 17 hours ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (181 reviews)

Attention to guest needs.

Reviewed on Feb 8, 2026

![The Whitney Hotel](https://images.trvl-media.com/lodging/30000000/29870000/29866100/29866090/59f2dc0e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Whitney Hotel

Beacon Hill

CA $1,254

per person

Mar 21 - Mar 25

found 24 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9.6/10 Exceptional! (482 reviews)

Excellent property conveniently located in Beacon Hill. Rooms are a tad on the small side but well appointed and clean.

Reviewed on Feb 7, 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 $1,080

per person

Mar 26 - Mar 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) 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

## 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)

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Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Fully refundableReserve now, pay when you stay

CA $192

CA $298 total

Mar 11 - Mar 12

includes taxes & fees

8.6/10 Excellent! (441 reviews)

Clean room, nice staff, the only problem was the internet was slow

Reviewed on Feb 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=12897&PinnedHotelID=12897&HadPinnedHotel=true&regionId=6285885)

![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Chatham Bars Inn

297 Shore Rd Chatham MA

CA $494

CA $565 total

Feb 11 - Feb 12

includes taxes & fees

9.2/10 Wonderful! (808 reviews)

Beautiful property

Reviewed on Jan 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=19139&PinnedHotelID=19139&HadPinnedHotel=true&regionId=6285885)

![Chatham Wayside Inn](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Chatham Wayside Inn

512 Main St Chatham MA

Fully refundableReserve now, pay when you stay

CA $182

CA $267 total

Feb 11 - Feb 12

includes taxes & fees

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

[](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=1517204&PinnedHotelID=1517204&HadPinnedHotel=true&regionId=6285885)

[See all 5,719 properties in South Dennis](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&regionId=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 $35

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 $69

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)

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