Dennis Port Vacations from $428

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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.

The Latest Dennis Port vacation packages

Price found within the past 48 hours. Click for updated prices.
EVEN Hotels Manchester Airport by IHG

EVEN Hotels Manchester Airport by IHG

3.5 out of 5
South End
Save 100% on your flight
Price was $676, price is now $428 per person
$428
per person
Nov 1 - Nov 8
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
8.8/10 Excellent! (892 reviews)
I was very impressed with the overall service and rooms. Large room, comfortable bed and pillows. Bathroom is also spacious and clean. The front desk staff remembered I had stayed with them a few days prior. Actually worth mentioning we did return right away for our flight out as it was so nice the prior stay. Only downfall was the breakfast, I didn't want to use the facility for breakfast but it was very generic offerings.

Reviewed on Aug 28, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,249, price is now $597 per person
$597
per person
Nov 11 - Nov 15
found 21 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Save 100% on your flight
Price was $1,332, price is now $882 per person
$882
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (168 reviews)
We’ve been to the Cape many times over the past 20 years. The Sesuit Harbor House was conveniently located off Route 6a, but it was very quiet; you couldn’t hear the traffic at all. Phil and his staff are very attentive and friendly; the continental breakfast in a basket every morning (with local treats) was perfect! We will come back and hopefully with more family members. It was 10/10!

Reviewed on Aug 25, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $2,469, price is now $1,722 per person
$1,722
per person
Nov 11 - Nov 15
found 21 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
I could not fault this hotel in any way. After long days out sightseeing and shopping it was great to get back and relax. This was our first time in Boston so we’re not sure which area was best to stay in. However the hotel’s location in Back Bay was excellent.

Reviewed on Aug 28, 2025

Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
Save 100% on your flight
Price was $723, price is now $515 per person
$515
per person
Oct 31 - Nov 3
found 12 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (874 reviews)
The staff at the property were very helpful and kind to my 1 year old. Many staff members went out of their way to say hello to him. The property was clean and the filtered water stations were a nice perk.

Reviewed on Aug 24, 2025

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Discover the most popular places to visit in Dennis Port

Sea Street Beach

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.

Sea Street Beach

Cape Cod Theatre Company – Home of the Harwich Jr. Theatre

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 seaside or attend a sporting event in this family-friendly area.

Cape Cod Theatre Company – Home of the Harwich Jr. Theatre

Swan Pond River

Commune with nature and explore the great outdoors at Swan Pond River during your travels in Dennis Port. Stroll along the waterfront or attend a sporting event in this family-friendly area.

Swan Pond River

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
$115 nightly
The price is $132 total per night from Sep 21 to Sep 22
$132 total
Sep 21 - Sep 22
Total with taxes and fees
Holiday Hill Inn & Suites
Oceanside Motel

Oceanside Motel

2 out of 5
329 Main Street, Dennis Port, MA
$79 nightly
The price is $90 total per night from Aug 31 to Sep 1
$90 total
Aug 31 - Sep 1
Total with taxes and fees
6.4/10 (590 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
$160 nightly
The price is $181 total per night from Sep 1 to Sep 2
$181 total
Sep 1 - Sep 2
Total with taxes and fees
Bluebird Dennisport
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.

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 0.5 miles from the city center.

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 travelers 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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Frequently asked questions

How much does a Dennis Port vacation package cost?
You'll find cheap prices from $428 on Expedia for your Dennis Port escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Dennis Port costs.
What are the cheapest months to go to Dennis Port?
October, November and December are great times to look for cheap Dennis Port vacation packages. Choosing to travel in less busy months means you can typically find reduced prices on hotels and flights.
How many days is enough for Dennis Port?
Usually, a handful of days is enough for a Dennis Port vacation. With a well-organized itinerary, you can check out all the main sights such as Swan Pond River, as well as discover some hidden treasures along the way.
Is it worth booking a vacation package to Dennis Port?
Boasting a host of highlights starting with its excellent watersports, Dennis Port is a good vacation destination. Whether you want to visit sights such as Sea Street Beach and Cape Cod Theatre Company – Home of the Harwich Jr. Theatre or venture off the beaten track, 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 cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most affordable Dennis Port package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Dennis Port vacation as a package?
You can enjoy significant savings on your next Dennis Port break by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Dennis Port?
Enjoy amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Dennis Port adventure.
Does Expedia offer Book Now, Pay Later Dennis Port vacation packages?
Jet off on your ideal getaway to Dennis Port with our Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until the next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stay on budget and snap up bargains before they disappear.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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