South Dennis Holidays

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Top Flight + Hotel Deals in South Dennis

Price found within the past 48 hours. Click for updated prices.
Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was €1,648, price is now €1,104 per person
€1,104
per person
8 Oct - 12 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,108 reviews)
Great place and location.

Reviewed on 26 Aug 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was €2,829, price is now €1,535 per person
€1,535
per person
8 Oct - 12 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on 24 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was €2,208, price is now €1,470 per person
€1,470
per person
28 Oct - 31 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
Lovely property and staff. Great location and spa. Will return!

Reviewed on 26 Aug 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was €1,673, price is now €1,134 per person
€1,134
per person
8 Oct - 12 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,073 reviews)
Always a great stay!

Reviewed on 26 Aug 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was €2,796, price is now €1,920 per person
€1,920
per person
8 Oct - 12 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Well appointed property, close to transit, downtown and highways. We had a lovely stay and look forward to returning soon.

Reviewed on 25 Aug 2025

Top hotels in South Dennis

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd, Hyannis, MA
Fully refundableReserve now, pay when you stay
The price is €198 per night from 14 Sept to 15 Sept
€198
14 Sept - 15 Sept
includes taxes & fees
8.6/10 Excellent! (291 reviews)
"Very family friendly, great pool, multiple fire pit for roasting marshmallows, indoor heated water park, arcade games. There is a cafe, a gift shop, a bar and restaurant with a door and out in the center of the resort where there is fire piths, a ballroom inside for free dance lessons. There is free ..."

Reviewed on 23 Aug 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
8.6/10 Excellent! (1,491 reviews)
"What a great resort. I would go there again."

Reviewed on 25 Aug 2025

Get rates
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
The price is €104 per night from 25 Sept to 26 Sept
€104
25 Sept - 26 Sept
includes taxes & fees
6.8/10 (863 reviews)
"Room was nice, lobby and outside is good enough. Would stay again."

Reviewed on 22 Aug 2025

Hyannis Plaza Hotel
See all 6,021 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.

What to do in South Dennis

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

€43
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Cape Cod Self-Guided Driving Audio Tour

Cape Cod Self-Guided Driving Audio Tour

€15
per traveller
100% of travellers recommend
Cape Cod Self-Guided Driving Audio Tour
Cape Cod and Provincetown Scenic Self-Guided Driving Audio Tour

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

€22
per traveller
80% of travellers recommend
Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour
See all activities in South Dennis

Frequently asked questions

How much does a South Dennis holiday package cost?
You'll find cheap prices from €1,104 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 holiday to South Dennis costs.
What are the cheapest months to go to South Dennis?
Plan your getaway for the off-peak season and you're likely to get cheap South Dennis holiday packages. Remember that public holidays and major local events can have an impact on prices, so do your research before booking.
How many days is enough for South Dennis?
Generally, a handful of days is enough to check out the top attractions during your South Dennis holiday. But if you'd like to have time to chill out or take day tours, consider 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 holiday as a package?
You can enjoy significant savings on your South Dennis escape by booking a customised holiday 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 holiday package to South Dennis?
If you're planning a spontaneous South Dennis holiday, 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 the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to South Dennis.
  2. Set your budget: Factor in expenses like flights, food and transportation when calculating how much to save for your trip to South Dennis. Then, choose a property that fits your budget, whether that's an economical option or a high-end retreat.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you'd like to experience in South Dennis. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customised South Dennis holiday package.

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