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.
The Whitney Hotel
Beacon Hill
CA $1,103
per person
Oct 25 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (611 reviews)
Great hotel in an excellent spot very nice facilities comfortable bed just everything you need for a city break in the heart of Beacon Hill
Reviewed on Sep 17, 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?
Dennis Port Hotel Deals
Holiday Hill Inn & Suites
352 Main Street Dennis Port MA
Fully refundableReserve now, pay when you stay
CA $165
CA $189 total
Sep 21 - Sep 22
includes taxes & fees
8.4/10 Very good! (1,006 reviews)
"Room was fine but the TV channels didn't work well for me. No local channels for sports like NESN,ESPN,"
Reviewed on Sep 18, 2026
The Corsair & Cross Rip Oceanfront Resort
41 Chase Ave Dennis Port MA
CA $134
CA $166 total
Sep 27 - Sep 28
includes taxes & fees
Dennis Port Surf Club (Boutique Hotel)
329 Main Street Dennis Port MA
Fully refundableReserve now, pay when you stay
CA $138
CA $157 total
Sep 22 - Sep 23
includes taxes & fees
9.4/10 Exceptional! (42 reviews)
"Amazing time ! Will be back"
Reviewed on Sep 17, 2026
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.
Stay near popular Dennis Port attractions
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.
Swan Pond River
8.4/10 (55 reviews)
Commune with nature and explore the great outdoors at Swan Pond River during your travels in Dennis Port. Stroll along the seaside or attend a sporting event in this family-friendly area.
Cape Cod Theatre Company – Home of the Harwich Jr. Theatre
7.6/10 (29 reviews)
You can get tickets for a performance at Cape Cod Theatre Company – Home of the Harwich Jr. Theatre during your stay in Northwest Harwich. Stroll along the waterfront or attend a sporting event in this family-friendly area.
Haigis Beach
7.8/10 (29 reviews)
Why not spend a lazy afternoon at Haigis Beach during your trip to Dennis Port? Wander the beautiful beaches and seaside in the area.
Swan Pond
Commune with nature and explore the great outdoors at Swan Pond during your travels in Dennis Port. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.
Frequently asked questions
How much does a Dennis Port vacation package cost?
You can snap up a vacation package to this destination from CA $1,103 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?
- 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.
- 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.
- 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.
- 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.
