Dennis Vacation Packages

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Your Dennis Vacation

Come and experience this wonderful city for yourself with a Dennis vacation package. Consider spending a few days in the neighborhood of Northwest Harwich, which is good for nature and walking, and your time here is bound to be unforgettable. If taking in sights is part of the plan during your trip to Dennis, visit major attractions like Cape Cod Museum of Art, Cape Cod Museum of Natural History and Mayflower Beach. Your dream Dennis vacation is a few clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your style.

Top Dennis Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8/10 Very Good! (2,052 reviews)
I stay at this property every August; one of the reasons I chose it was access to a pool. When I arrived, there was a sign saying the pool was being “renovated”. Had I known, I would have chosen a different hotel. BTW: Their website still lists a pool as one of their amenities. Very dishonest.

Reviewed on Aug. 5, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (132 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on Aug. 5, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on Aug. 3, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (428 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 Jul. 25, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (569 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 Aug. 2, 2025

Dennis Beach Vacation

There's nothing more relaxing than a Dennis vacation. Whether you're treating yourself to refreshing cocktails at a local bar or flipping through a magazine along the water's edge, your trip to Dennis is the time to live out your beachy daydreams. Many visitors will tell you to stay near Mayflower Beach, situated just 2 kilometres from the centre of town. However, you'll also discover an excellent range of Dennis vacation packages around Corporation Beach and Bayview Beach, two other well-liked nearby options.

Things You Should Know About Dennis

  • If your idea of a perfect escape is fresh sea air and water views, check out our Dennis beach hotels. You're sure to forget the pressures of daily life at these blissful beachy retreats.
  • Alternatively, check out our range of private vacation homes. They're popular with travellers planning a vacation in Dennis. Begin your search with Sesuit Harbour House and Starlight Lodge Cape Cod.
  • Our Dennis things to do page is an excellent place to discover fun activities around here. Of course, it's hard to beat a little local knowledge. With a population of 6,096 cm Dennis, we're sure you'll find a few friendly people willing to give you some tips.
  • Dennis vacation deals are an excellent way to save on exciting experiences. Some ideas, such as Mayflower Beach, Mayflower Beach and Corporation Beach, should be at the top of your sightseeing list.

Ready to book your vacation to Dennis?

 

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Dennis Hotel Deals

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
1421 Main Street, Dennis, MA
Fully refundableReserve now, pay when you stay
The price is CA $366 per night from Sep 2 to Sep 3
CA $366
CA $419 total
Sep 2 - Sep 3
includes taxes & fees
9.6/10 Exceptional! (156 reviews)
"Easy check-in process without having to go to a desk. Very nice amenities and comfort. The hotel is old with low ceilings and small bathroom. A/C unit is noisy but worked very well."

Reviewed on Jul. 31, 2025

Sesuit Harbor House
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 CA $134 per night from Sep 7 to Sep 8
CA $134
CA $167 total
Sep 7 - Sep 8
includes taxes & fees
6.8/10 (828 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 Aug. 6, 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 CA $247 per night from Sep 1 to Sep 2
CA $247
CA $299 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,441 reviews)
"Great space, clean and comfortable."

Reviewed on Aug. 4, 2025

Bayside Resort Hotel
See all 6,157 properties in 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.
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Discover the most popular places to visit in Dennis

Mayflower Beach

Mayflower Beach

5/5(3 reviews)

Why not spend a carefree afternoon at Mayflower Beach during your travels in Dennis? While you're in the area, stroll along the waterfront.

Mayflower Beach

What to do in Dennis

Cape Cod and Provincetown Scenic Self-Guided Driving Audio Tour

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

CA $34
per traveller
80% of travellers recommend
Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour
Cape Cod Self-Guided Driving Audio Tour

Cape Cod Self-Guided Driving Audio Tour

CA $23
per traveller
100% of travellers recommend
Cape Cod Self-Guided Driving Audio Tour
Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

CA $69
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
See all activities in Dennis

Frequently asked questions

How much does a Dennis vacation package cost?
You can snap up a vacation package to this destination from CA $1,066 on Expedia. However, how much your vacation to Dennis costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Dennis?
The off-season is the best time to travel to Dennis if you're trying to save. Another tip for scoring cheap Dennis vacation packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Dennis?
Dennis vacations can be as short or long as you like, but to get a true feel for this destination, we reckon 3 days is about right. In this timeframe, you can fit in top attractions like Cape Cod Rail Trail and Corporation Beach as well as lesser-known gems. Don't miss out on neighbourhoods such as Bass River and Northwest Harwich either. If you plan wisely, you can even schedule a day trip or two from Dennis too.
Is it worth booking a vacation package to Dennis?
Whether you're planning to check out attractions like Mayflower Beach and Corporation Beach, or want to experience its top-notch walking trails and coastal beaches, a Dennis vacation is sure to exceed your expectations. Book your trip with Expedia and discover why Dennis is such a good vacation destination.
How to find the best Dennis package deals?
Finding a cheap Dennis package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Dennis package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Dennis vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still have the freedom to create a customized Dennis vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Dennis?
If you have your Dennis vacation dates locked in, book as soon as you can to grab some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Dennis?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Dennis.
  2. Budget wisely: On top of the price of your accommodations, you'll need to factor in other expenses too. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Dennis.
  3. Decide how long to go for: Now that you're up to speed on Dennis, you can work out the perfect length of your vacation. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: Once you've settled on your dates and duration, lock in the right Dennis vacation package for you.

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