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 $1,431, price is now CA $681 per person
CA $681
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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 $1,553, price is now CA $995 per person
CA $995
per person
Dec 11 - Dec 13
just found
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,964, price is now CA $1,386 per person
CA $1,386
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,530, price is now CA $1,101 per person
CA $1,101
per person
Jan 28 - Jan 31
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was CA $2,606, price is now CA $1,925 per person
CA $1,925
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.4/10 Exceptional! (491 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 $493 per night from Nov 8 to Nov 9
CA $493
CA $564 total
Nov 8 - Nov 9
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
Hyannis Travel Inn

Hyannis Travel Inn

2.5 out of 5
18 North St Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Nov 3 to Nov 4
CA $138
CA $158 total
Nov 3 - Nov 4
includes taxes & fees
Hyannis Travel Inn
See all 5,662 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 $681 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.