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.
Chateau Merrimack Resort & Spa

Chateau Merrimack Resort & Spa

4.5 out of 5
Price was CA $1,181, price is now CA $821 per person
CA $821
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8/10 Very Good! (552 reviews)
Property was clean and the employees were always nice and helpful

Reviewed on Sep. 5, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $1,394, price is now CA $918 per person
CA $918
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,028 reviews)
Great location. Reliable accommodation.

Reviewed on Sep. 4, 2025

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
South End
Price was CA $2,073, price is now CA $1,372 per person
CA $1,372
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,003 reviews)
This property was in such a great area and walkable distance to many sights in Boston. I traveled for a birthday and they accommodated decorations free of charge. The staff were on site late into the night and available to help. Room was comfortable and the Trophy Room restaurant on the bottom floor was nice and LGBTQ+ friendly.

Reviewed on Sep. 5, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was CA $2,325, price is now CA $1,545 per person
CA $1,545
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,122 reviews)
Great staff, good location

Reviewed on Sep. 5, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was CA $2,230, price is now CA $1,498 per person
CA $1,498
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (593 reviews)
Good location. Think the following items should have been in the unit: Tea towel, dish cloth, paper towels, sink stopper and 4 coffees (for 4 individuals). Both shower stalls should include shelves for shampoo, soap etc. FYI, the glass stove top has brown stains. The concierges were very friendly and helpful.

Reviewed on Aug. 31, 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.

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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 $158 per night from Sep 14 to Sep 15
CA $158
CA $180 total
Sep 14 - Sep 15
includes taxes & fees
Holiday Hill Inn & Suites
Oceanside Motel

Oceanside Motel

2 out of 5
329 Main Street, Dennis Port, MA
Get rates
Oceanside Motel
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 $205 per night from Sep 14 to Sep 15
CA $205
CA $247 total
Sep 14 - Sep 15
includes taxes & fees
The Corsair & Cross Rip Oceanfront Resort
See all 493 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.