South Dennis Vacations from $364

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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.

The Latest South Dennis vacation packages

Price found within the past 48 hours. Click for updated prices.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Price was $514, price is now $364 per person
$364
per person
May 4 - May 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.2/10 Wonderful! (253 reviews)
Room was not easy to get to and it was 0 degrees out …1st they put me out in a building where the property was a sheet of ice so I asked to be moved to the main building since I was by myself. Fortunately, they moved me, but the room was confusing to get to. :-( The pool was closed for maintenance, and I was planning to swim. :-( The room was great, clean and a comfortable bed, so I would stay again, but I would request staying closer to the lobby next time.

Reviewed on Jan 31, 2026

Beachside Village Resort

Beachside Village Resort

3 out of 5
Save 100% on your flight
Price was $911, price is now $587 per person
$587
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (101 reviews)
Very clean and quiet place to relax. Very friendly and professional! We will come back!

Reviewed on Nov 10, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was $1,210, price is now $793 per person
$793
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.6/10 Exceptional! (251 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,707, price is now $1,139 per person
$1,139
per person
May 14 - May 16
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
Excellent hotel- restaurants, room service, all of the staff, spacious room with view, bathroom amenities. Great location. Able to take a leisurely walk along the water, and close to many restaurants and theatre district. Also easy to catch a taxi or uber. Wonderful setting with water and city view. Will definitely return!

Reviewed on Mar 14, 2026

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Save 100% on your flight
Price was $817, price is now $566 per person
$566
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
8.6/10 Excellent! (473 reviews)
Stayed here during snow storm. Enjoyed comfortable accomodations and wonderful staff. Clean and quiet.

Reviewed on Mar 15, 2026

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Discover the most popular places to visit in South Dennis

Cape Cod Rail Trail

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.

Cape Cod Rail Trail

What to do in South Dennis

Cape Cod Self-Guided Driving Audio Tour

Cape Cod Self-Guided Driving Audio Tour

$17
per traveler
100% of travellers recommend
Cape Cod Self-Guided Driving Audio Tour
Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

$50
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
See all activities in South Dennis

South Dennis Hotel Deals

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
$182 nightly
The price is $209 total per night from Mar 19 to Mar 20
$209 total
Mar 19 - Mar 20
Total with taxes and fees
8.8/10 Excellent! (489 reviews)
Beautiful place

Reviewed on Mar 15, 2026

Margaritaville Resort Cape Cod
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $141 total per night from Apr 12 to Apr 13
$141 total
Apr 12 - Apr 13
Total with taxes and fees
8.8/10 Excellent! (1,551 reviews)
The cost for this place was over priced for the accommodations. Breakfast was nothing to talk about the whirlpool was load when draining and could here other filling theirs.

Reviewed on Mar 15, 2026

Bayside Resort Hotel
Aiden by Best Western Cape Cod - West Yarmouth

Aiden by Best Western Cape Cod - West Yarmouth

3 out of 5
476 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $111 total per night from Mar 24 to Mar 25
$111 total
Mar 24 - Mar 25
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
We stayed during the blizzard of 2026, so it may have been a harder time to keep everything clean, but the carpets on the stairs and in the hallways were very dirty, and the door to our bathroom wasn’t wiped down. Breakfast was good if you steered clear of the eggs and home fries and just stuck to ...

Reviewed on Mar 4, 2026

Aiden by Best Western Cape Cod - West Yarmouth
See all 5,739 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.

Find the Best South Dennis Vacation Packages

South Dennis Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Barnstable Municipal Airport (HYA)
Population
3,600
Max Temp Winter
40ºF
Max Temp Summer
70ºF
Top Sights
Cape Cod Inflatable Park, Cape Codder Water Park and Mayflower Beach

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Frequently asked questions

How much does a South Dennis vacation package cost?
You'll find cheap prices from $364 on Expedia for your South Dennis getaway. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to South Dennis costs.
What are the cheapest months to go to South Dennis?
If you'd like to book a cheap South Dennis vacation package, consider traveling in November, December and January. You'll typically find better prices on hotels and flights during these months — ideal for budget-conscious travelers.
How many days is enough for South Dennis?
Generally, a handful of days is enough to see the major attractions during your South Dennis vacation. However, if you'd like to have more time to relax or go on day trips, think about extending your itinerary.
How to find the best South Dennis package deals?
Start your search for a South Dennis package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal South Dennis package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your South Dennis escape off to a flying start.
Is it cheaper to book a South Dennis vacation as a package?
You can enjoy significant savings on your South Dennis escape by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to South Dennis?
If you're planning a spontaneous South Dennis vacation, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to South Dennis?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to visit South Dennis.
  2. Plan your budget wisely: On top of the cost of your stay, you'll need to factor in other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that may come up during your trip to South Dennis.
  3. Explore South Dennis using our trip planning tool: Gain insights into the most popular attractions and best properties for your trip to South Dennis. You can also save your favorite places, collaborate with friends and family and manage all your plans in one place.
  4. Decide how long to go away for: Now that you know more about South Dennis, you can work out the perfect length of your break. Create a rough itinerary and give yourself enough time for all the things you want to do.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a South Dennis vacation package that brings all your bookings together.
  6. Book experiences or activities ahead of time: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on South Dennis's highlights. Find all the incredible things to do in South Dennis with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later South Dennis vacation packages?
Jet off on your dream trip to South Dennis with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snap up travel deals while they last.

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