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.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
24 Oct - 29 Oct
found 9 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
27 Oct - 1 Nov
found 18 hours ago
Return direct flight included
Dublin (DUB) 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 11 Aug 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Save 100% on your flight
per person
24 Oct - 29 Oct
found 9 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8/10 Very Good! (571 reviews)
Washer/Dryer did not work properly. Despite 2 calls and 1 email to customer service, the issue was not resolved. The washer didn’t rinse clothing out and they remained sopping wet. They required extensive drying time as a result ( over 4 hours). This was extremely inconvenient.

Reviewed on 2 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
27 Oct - 1 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (433 reviews)
Had an amazing time at the Whitney. Front desk service was impeccable, friendly and was ‘just’ the added touch I would expect of a property of this caliber. I really do look forward to my next time in Boston and hope to stay at the Whitney.

Reviewed on 25 Jul 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Save 100% on your flight
per person
27 Oct - 1 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,102 reviews)
This hotel is within walking distance to most of Boston’s historic sites, Fenway and the T (subway).

Reviewed on 9 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 €229 per night from 1 Sept to 2 Sept
€229
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (261 reviews)
"There’s comfortable beds ."

Reviewed on 8 Aug 2025

Margaritaville Resort Cape Cod
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 9 Sept to 10 Sept
€104
9 Sept - 10 Sept
includes taxes & fees
6.8/10 (832 reviews)
"The room was clean and very comfortable, and the bathroom was also immaculate with a very good shower. The TV was really easy to work and also nice and big"

Reviewed on 6 Aug 2025

Hyannis Plaza Hotel
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is €231 per night from 24 Aug to 25 Aug
€231
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (1,456 reviews)
"Beautiful location. Clean, tidy, comfortable rooms. Excellent facilities. Good customer service with helpful and friendly staff. Very good breakfast options. Would recommend."

Reviewed on 9 Aug 2025

Bayside Resort Hotel
See all 6,014 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 €1,009 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.