Dennis Port Vacation Packages

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Your Dennis Port Vacation

With all your travel needs organized before you set off, our Dennis Port vacation packages mean you can simply focus on having a good time! One neighborhood to base yourself in this captivating city is Northwest Harwich, which is great for nature and walking. Cape Cod Inflatable Park, West Dennis Beach and Seagull Beach are just some of the many attractions you'll want to explore during your trip to Dennis Port. Expedia has what you need to escape the everyday. Tailor your vacation to Dennis Port to suit your travel style, whatever that may be.

Top Dennis Port Vacation Deals

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 CA $1,062, price is now CA $590 per person
CA $590
per person
Nov 1 - Nov 3
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was CA $1,563, price is now CA $1,038 per person
CA $1,038
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (162 reviews)
Phil’s property is immaculate and the rooms are very clean and will all required amenities. Phil’s hospitality is also top notch and it will be my place to stay in my future cape cod visits!!

Reviewed on Aug. 20, 2025

Cambria Hotel & Suites Plymouth

Cambria Hotel & Suites Plymouth

3 out of 5
Price was CA $994, price is now CA $679 per person
CA $679
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (18 reviews)
We’d love to come back here.

Reviewed on Aug. 22, 2025

Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Price was CA $1,051, price is now CA $725 per person
CA $725
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8.4/10 Very Good! (319 reviews)
Great stay at an amazing locations. No issues we had a blast. They were so welcoming and inviting and the room was clean and comfortable.

Reviewed on Aug. 23, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was CA $1,545, price is now CA $1,078 per person
CA $1,078
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (585 reviews)
The location was great and we were able to get to all the sites easily. Also, liked having two beds and two bathrooms for the price. However, everything was very cheap in there. The sheets were nubbie because they were cheap and worn. The toliet paper was so awful we had to buy our own. The beds had little support. The place was clean though. So if you don't care much about the bed, sheets, and toliet paper it is a good pick. If you do maybe pick somewhere else.

Reviewed on Aug. 17, 2025

Dennis Port Beach Vacation

Forget the stresses of daily life and let your mind, body and soul unwind on your Dennis Port vacation. There's nothing more invigorating than a cool ocean breeze and the soothing melody of waves crashing onto the shore. Plan your trip to Dennis Port the easy way by choosing one of our Dennis Port vacation deals. Many people decide to spend their nights near Sea Street Beach, a local highlight just 0.80 kilometres from the city centre.

Things You Should Know About Dennis Port

  • Reserve a room in one of our Dennis Port beach hotels and experience this destination at its best. Wander along the water's edge and watch some stunning sunrises right outside your front door.
  • Our private vacation homes, like The Corsair & Cross Rip Oceanfront Resort and Bluebird Dennisport, are popular with travellers of all sorts. Consider the amenities and get set for your stay in Dennis Port!
  • Some 3,200 people live in Dennis Port. If you're after suggestions about what to see and do around these parts, why not start a conversation with one or two of the locals? Our Dennis Port things to do page is also a handy source of information.
  • Sea Street Beach, Sea Street Beach and Cape Cod Theatre Company – Home of the Harwich Jr. Theatre are some great sights that should be on your travel agenda. With our Dennis Port vacation deals, you'll have more money in your back pocket to explore.

Ready to book your vacation to Dennis Port?

 

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Dennis Port Hotel Deals

Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

2 out of 5
352 Main Street, Dennis Port, MA
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Sep 21 to Sep 22
CA $159
CA $182 total
Sep 21 - Sep 22
includes taxes & fees
8.2/10 Very Good! (910 reviews)
Dennisport
"Great stay Would come again!"

Reviewed on Aug. 23, 2025

Holiday Hill Inn & Suites
Oceanside Motel

Oceanside Motel

2 out of 5
329 Main Street, Dennis Port, MA
The price is CA $109 per night from Aug 25 to Aug 26
CA $109
CA $125 total
Aug 25 - Aug 26
includes taxes & fees
6.4/10 (587 reviews)
"I liked every aspect of my stay."

Reviewed on Aug. 21, 2025

Oceanside Motel
Bluebird Dennisport

Bluebird Dennisport

3 out of 5
426 Lower County Rd, Dennis Port, MA
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Sep 1 to Sep 2
CA $194
CA $250 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (194 reviews)
"Good location and comfortable bed"

Reviewed on Aug. 22, 2025

Bluebird Dennisport
See all 496 properties in Dennis Port
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Dennis Port vacation package cost?
You can snap up a vacation package to this destination from CA $590 on Expedia. But how much your vacation to Dennis Port costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Dennis Port?
If you're looking to snag a cheap Dennis Port vacation package, consider visiting in January, February and March. You'll typically find better rates on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Dennis Port?
To fully enjoy your Dennis Port vacation, we suggest staying for 3 days. Split your time between discovering Cape Cod Rail Trail, Sea Street Beach and other must-see attractions, on top of exploring neighbourhoods like Bass River and South Chatham. If you've got some time to spare, add a tour or day trip to your Dennis Port vacation itinerary.
Is it worth booking a vacation package to Dennis Port?
Boasting a host of highlights starting with its top-notch watersports, Dennis Port is a good vacation destination. Whether you want to check out sights like Sea Street Beach and Cape Cod Theatre Company – Home of the Harwich Jr. Theatre or take the path less travelled, you'll have plenty to see and do on your Dennis Port vacation.
How to find the best Dennis Port package deals?
Bagging a cheap Dennis Port package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most economical Dennis Port package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Dennis Port vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and hotels individually. Better still, you can tailor your Dennis Port getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Dennis Port?
If you've got your Dennis Port travel dates confirmed, book as early as you can to snap up some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Dennis Port?

  1. Choose when to travel: Check your calendar and get packing. Your favourite time of year and the type of activities on offer will also help you decide when to visit Dennis Port.
  2. Set your budget: Consider costs like food, flights and transportation when calculating how much to put aside for your trip to Dennis Port. Then, pick a property that fits your budget, whether that's a wallet-friendly stay or a more luxurious getaway.
  3. Decide how long to go for: Now that you're up to speed on Dennis Port, you can figure out the right length of your vacation. Put together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Dennis Port vacation package that brings all your bookings together.

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