South Dennis Vacations

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Find the Best South Dennis Vacation Packages

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
The price is AED 567 per night from Feb 10 to Feb 11
AED 567
AED 859 total
10 Feb - 11 Feb
includes taxes & fees
8.6/10 Excellent! (441 reviews)
Clean room, nice staff, the only problem was the internet was slow

Reviewed on 2 February 2026

Margaritaville Resort Cape Cod
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is AED 1,337 per night from Feb 11 to Feb 12
AED 1,337
AED 1,530 total
11 Feb - 12 Feb
includes taxes & fees
9.2/10 Wonderful! (808 reviews)
Beautiful property

Reviewed on 24 January 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (629 reviews)
Courteous staff, helpful with dining suggestions. Loved the room. Very comfortable bed, warm and cozy.

Reviewed on 29 January 2026

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Chatham Wayside Inn
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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.

Frequently asked questions

How do I find cheap flights to South Dennis that have flexible change policies?
Search for cheap flights to South Dennis, then click on "No change fee" underneath the "Flexible change policies" heading. It really is that easy. We know that plans change and flexibility is important, so you can book with confidence with Expedia.
Which airlines fly to South Dennis?
You can take your pick of a variety of airlines with flights into or near South Dennis. Some of your top options are:

  • Delta Air Lines - 3,701 flights to or near South Dennis each month, including 3,701 flights to Logan Intl. Airport (BOS) per month.
  • JetBlue Airways - 3,407 flights to or near South Dennis each month, including 3,407 flights to Logan Intl. Airport (BOS) per month.
  • American Airlines - 2,106 flights to or near South Dennis each month, including 2,106 flights to Logan Intl. Airport (BOS) per month.

How can I find cheap tickets to South Dennis?
You'll always nab an awesome deal with Expedia, but our "flexible dates" feature makes it even easier. Enter your preferred travel date, then click on the flexible dates box above to see the cheapest prices for nearby days. was the best price for a flight to South Dennis in the last seven days.
How much is a flight to South Dennis?
You could have nabbed a return ticket to South Dennis from anywhere between and in the last seven days. For one-way journeys leaving from (), the lowest amount paid during this time was .
What are the most popular airports to fly into in South Dennis?
Depending on your budget, airline and departure city, one of these major airports will be your gateway to South Dennis:

  • Logan Intl. Airport (BOS) - 12,948 flights per month.
  • Barnstable Municipal Airport (HYA) - 160 flights per month.

When is the cheapest time to fly to South Dennis?
If you'd prefer to spend your hard-earned vacation money experiencing the delights of South Dennis rather than on your flight there, jet off early in the week. The most affordable day to travel is generally Tuesday, followed by Monday. With many folks keeping their travel to weekends, Saturday typically has the most expensive airfares.
How much is a plane ticket to South Dennis?
In the last seven days, flights to South Dennis ranged from to .
What months are the cheapest to book a flight to South Dennis?
Score a ticket in February for incredible flight deals to South Dennis. December is generally the most expensive time to buy an airfare.
How long is a flight to South Dennis?
Whether or not you'll have time to read one chapter of your book or a few depends on where you're flying from in the States. To give you a rough estimate, here are the average flight times for three busy domestic routes to South Dennis:

  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 48 minutes
  • New York, NY (LGA-LaGuardia) to Logan Intl. Airport (BOS) - 1 hour and 35 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Logan Intl. Airport (BOS) - 1 hour and 25 minutes