South Dennis Vacations from $310

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $635, price is now $310 per person
$310
per person
Nov 1 - Nov 3
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,068, price is now $622 per person
$622
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,679 reviews)
I would stay here again in a heartbeat. They were efficient, extremely friendly, clean and fun environment. The location is excellent and the Irish pub in the adjacent location to the lobby was super convenient. This is what Boston is all about!

Reviewed on Aug 19, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $3,070, price is now $1,840 per person
$1,840
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on Aug 11, 2025

Fairfield Inn & Suites by Marriott Plymouth

Fairfield Inn & Suites by Marriott Plymouth

2.5 out of 5
Save 100% on your flight
Price was $505, price is now $321 per person
$321
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (471 reviews)
Clean and comfortable. Very easy to park.

Reviewed on Aug 5, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $1,328, price is now $845 per person
$845
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (1,102 reviews)
This is our go-to in Boston. Super convenient, clean and modern!

Reviewed on Aug 19, 2025

Don't see what you're looking for?
See all available trips from Columbus to South Dennis
View all trips

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

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

$50
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
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
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
$201 nightly
The price is $230 total per night from Sep 14 to Sep 15
$230 total
Sep 14 - Sep 15
Total includes taxes and fees
8.6/10 Excellent! (277 reviews)
"All good stuff - exception AC shuts down in middle of night. No way to make fan ON always. Not good for me and family to sleep."

Reviewed on Aug 18, 2025

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
$190 nightly
The price is $217 total per night from Sep 3 to Sep 4
$217 total
Sep 3 - Sep 4
Total includes taxes and fees
8.6/10 Excellent! (1,482 reviews)
"Great central location. Outdoor grounds relaxing with nice views. Staff was friendly."

Reviewed on Aug 17, 2025

Bayside Resort Hotel
Hyannis Plaza Hotel

Hyannis Plaza Hotel

2.5 out of 5
662 Main Street, Hyannis, MA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $118 total per night from Sep 2 to Sep 3
$118 total
Sep 2 - Sep 3
Total includes taxes and fees
6.8/10 (856 reviews)
"Great value. Newly remodeled rooms. Very clean. Relaxed atmosphere. Nice pool. Great location on Main Street in Hyannis. I highly recommend this hotel."

Reviewed on Aug 18, 2025

Hyannis Plaza Hotel
See all 6,029 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a South Dennis vacation package cost?
You'll find cheap prices from $310 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.