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.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,287, price is now CA $924 per person
CA $924
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (193 reviews)
The location couldn’t have been more perfect and despite it being a holiday weekend the parking lot/BNB never felt crowded. Everyone we encountered was lovely and helpful, and the room was a perfect place to take a midday nap or unwind after hours on the beach! We would definitely stay again.

Reviewed on Jul 6, 2026

The Charles Hotel

The Charles Hotel

5 out of 5
West Cambridge
Price was CA $2,028, price is now CA $1,328 per person
CA $1,328
per person
Aug 12 - Aug 16
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (1,002 reviews)
Great experience but check in was delayed for a while and ended up in a different room category but hotel is beautiful and centrally located.

Reviewed on Jul 5, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,611, price is now CA $2,537 per person
CA $2,537
per person
Sep 17 - Sep 20
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Price was CA $5,480, price is now CA $3,971 per person
CA $3,971
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on Oct 8, 2025

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $3,063, price is now CA $2,240 per person
CA $2,240
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (720 reviews)
Chatham Tides is a slice of heaven. Beautiful location. Clean, well maintained. Staff was super helpful with local restaurants. My wife and I gave it a 11/10

Reviewed on Jul 2, 2026

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 $228 per night from Aug 2 to Aug 3
CA $228
CA $261 total
Aug 2 - Aug 3
includes taxes & fees
8.4/10 Very good! (991 reviews)
"Being an older hotel, it was very clean and well-maintained. It’s affordable and totally fine for a place to lay your head.."

Reviewed on Jul 3, 2026

Holiday Hill Inn & Suites
The Corsair & Cross Rip Oceanfront Resort

The Corsair & Cross Rip Oceanfront Resort

2.5 out of 5
41 Chase Ave Dennis Port MA
The price is CA $410 per night from Jul 28 to Jul 29
CA $410
CA $481 total
Jul 28 - Jul 29
includes taxes & fees
8.6/10 Excellent! (262 reviews)
"hot tub was down. would've been nice to know. otherwise, just a fantastic private beach/ resort. staff super friendly. property immaculate for meeting next to the beach"

Reviewed on Jul 5, 2026

The Corsair & Cross Rip Oceanfront Resort
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 $320 per night from Jul 7 to Jul 8
CA $320
CA $399 total
Jul 7 - Jul 8
includes taxes & fees
8.4/10 Very good! (227 reviews)
"Great location, walking distance from a few different beaches and restaurants. The room was very clean, and the grills and pool area were great!"

Reviewed on Jul 6, 2026

Bluebird Dennisport
See all 513 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

Stay near popular Dennis Port attractions

An aerial view of a coastal town with a beach, houses, and a bay.

Sea Street Beach

8.6/10 (122 reviews)
If a restful vacation is part of your travel plans, Sea Street Beach might be the perfect place to seek out during your trip to Dennis Port. Wander the area's seaside or simply enjoy one of its top-notch restaurants.
See properties

Frequently asked questions

How much does a Dennis Port vacation package cost?
You can snap up a vacation package to this destination from CA $924 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.

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