South Dennis Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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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.
The Colonnade Hotel Back Bay
Back Bay
CA $1,278
per person
Nov 8 - Nov 12
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (2,493 reviews)
Perfect location in Back Bay. Used Logan Express from/to airport and drop off walkable distance from 800 Boylston. The green line right outside front door. The bed were comfortable, helpful staff. Will definitely return !
Reviewed on Sep 29, 2026
The Monty Boston
Downtown Boston
CA $4,374
per person
Dec 10 - Dec 17
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
9.6/10 Exceptional! (40 reviews)
We loved the location and the host was amazing. We only wish the sidewalk construction wasn’t going on because it obstructed part of the beautiful view.
Reviewed on Sep 21, 2026
Four Seasons Hotel Boston
Bay Village
CA $1,966
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (485 reviews)
Room was very noisy in the morning and I could not sleep. Work is being done in the building and I was not informed of when arriving from west coast to stay for one night. Staff was very friendly and apologetic.
Reviewed on Sep 25, 2026
Ready to book your vacation to South Dennis?
South Dennis Hotel Deals
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
CA $190
CA $299 total
Oct 25 - Oct 26
includes taxes & fees
8.6/10 Excellent! (784 reviews)
"K"
Reviewed on Sep 28, 2026
Bayside Resort Hotel
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
CA $168
CA $209 total
Oct 28 - Oct 29
includes taxes & fees
Uncommoner Hotel by Reverie Boutique Collection
135 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
CA $168
CA $199 total
Oct 14 - Oct 15
includes taxes & fees
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.
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.
What to do in South Dennis
Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour
CA $35
per traveller
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
CA $70
per adult
Frequently asked questions
How much does a South Dennis vacation package cost?
You'll find cheap prices from CA $1,119 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?
- 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.
- 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.
- 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.
- 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.
