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, Cape Cod Museum of Natural History and Mayflower Beach. 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 Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,526, price is now CA $754 per person
CA $754
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,135, price is now CA $1,148 per person
CA $1,148
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,566, price is now CA $1,038 per person
CA $1,038
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
Price was CA $23,493, price is now CA $15,772 per person
CA $15,772
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Provincetown (PVC)
8.4/10 Very good! (1,003 reviews)

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,897, price is now CA $1,309 per person
CA $1,309
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

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South Dennis Hotel Deals

Cape Cod's "Beach Rose"

Cape Cod's "Beach Rose"

Dennis MA
10/10 Exceptional! (38 reviews)
"The house was a perfect fit for our crew. The house had all the features stated in the listing, house was clean and organized. Louise allowed us to arrive early and accompanied our stay. We most certainly would return!"

Reviewed on Nov 1, 2026

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Cape Cod's "Beach Rose"
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is CA $515 per night from Nov 19 to Nov 20
CA $515
CA $590 total
Nov 19 - Nov 20
includes taxes & fees
9.2/10 Wonderful! (876 reviews)
"Amazing place to stay. Can't wait to go back."

Reviewed on Oct 30, 2026

Chatham Bars Inn
Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

3 out of 5
867 Iyannough Road Hyannis MA
The price is CA $180 per night from Nov 21 to Nov 22
CA $180
CA $207 total
Nov 21 - Nov 22
includes taxes & fees
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
See all 5,637 properties in South Dennis
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.
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Stay near popular South Dennis attractions

Cape Cod Rail Trail

9.2/10 (10 reviews)
Enjoy a trip to Cape Cod Rail Trail and popular activities like golfing in South Dennis. Wander the beautiful beaches and waterfront in this family-friendly area.
See properties

What to do in South Dennis

Cape Cod and Provincetown Scenic Self-Guided Driving Audio Tour

Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour

CA $36
per traveller
Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)

CA $71
per adult
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
Self Guided Driving Audio Tour Cape Cod

Self Guided Driving Audio Tour Cape Cod

CA $24
per traveller
Self Guided Driving Audio Tour Cape Cod
See all activities in South Dennis

Frequently asked questions

How much does a South Dennis vacation package cost?
You'll find cheap prices from CA $754 on Expedia for your South Dennis break. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to South Dennis costs.
What are the cheapest months to go to South Dennis?
To pick up cheap South Dennis vacation packages, plan your trip outside of busy periods like public holidays and major events. You'll generally find better availability and lower prices for hotels and flights.
How many days is enough for South Dennis?
We'd recommend booking a South Dennis vacation for around 5 days. This will allow you time to visit major attractions such as Corporation Beach and Sea Street Beach, and also check out neighbourhoods like Bass River and Northwest Harwich. You might even be able to squeeze in a day trip outside of South Dennis.
How to find the best South Dennis package deals?
Use Expedia's handy filters to find some great South Dennis package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for South Dennis package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a South Dennis vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized South Dennis vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to South Dennis?
If you've got your South Dennis vacation dates locked in, book as early as you can to score some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to South Dennis?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to South Dennis.
  2. Set your budget: Factor in expenses such as food, flights and transportation when working out how much to set aside for your trip to South Dennis. Then, pick a property that matches your budget, whether that's a low-cost option or a high-end getaway.
  3. Decide your trip length: Consider how long you want to spend exploring South Dennis. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized South Dennis vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.