Dennis Port Vacations 2026 from CA $1,481

Dennis Port flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Fairmont Copley Plaza, Boston

Back Bay

CA $1,481

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Four Seasons Hotel Boston

Bay Village

CA $2,536

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.

Boston Harbor Hotel

North End

CA $2,869

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Fredericton (YFC) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

The Langham, Boston

Downtown Boston

CA $1,846

per person

Oct 1 - Oct 4

found 19 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.

Raffles Boston

Back Bay

CA $2,865

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Top Dennis Port hotels deals

Holiday Hill Inn & Suites

352 Main Street Dennis Port MA

CA $159

CA $182 total

Sep 9 - Sep 10

includes taxes & fees

Book a stay at this family-friendly motel in Dennis Port. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions West Dennis Beach and Harwich Port are located nearby.

Pool

Parking included

The Corsair & Cross Rip Oceanfront Resort

41 Chase Ave Dennis Port MA

CA $270

CA $321 total

Sep 9 - Sep 10

includes taxes & fees

Book a stay at this beach hotel in Dennis Port. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions West Dennis Beach and Harwich Port are located nearby.

Bluebird Dennisport

426 Lower County Rd Dennis Port MA

Free cancellation

Reserve now, pay when you stay

CA $284

CA $357 total

Aug 27 - Aug 28

includes taxes & fees

Stay at this hotel in Dennis Port. Enjoy free WiFi, an outdoor pool, and housekeeping. Popular attractions West Dennis Beach and Harwich Port are located nearby.

Pool

Pet-friendly

Dennis Port Surf Club (Boutique Hotel)

329 Main Street Dennis Port MA

Free cancellation

Reserve now, pay when you stay

CA $312

CA $358 total

Aug 26 - Aug 27

includes taxes & fees

Book a stay at this golf motel in Dennis Port. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions West Dennis Beach and Harwich Port are located nearby.

By the Sea Guests Bed & Breakfast & Suites

57 Chase Avenue & Inman Road Extension Dennis Port MA

Get rates

Book a stay at this beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions West Dennis Beach and Harwich Port are located nearby.

Kingfisher Oceanside

15 Sea St Dennis Port MA

CA $247

CA $282 total

Sep 7 - Sep 8

includes taxes & fees

Book a stay at this beach motel in Dennis Port. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions West Dennis Beach and Harwich Port are located nearby.

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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

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

Dennis Port Vacations

Have more fun, worry less and wander wisely in Dennis Port! Get your adventure off to a winning start by learning the basics about this interesting destination.

From the heart of Cape Cod, you'll need to journey southeast for 9 miles (14 kilometers) to reach this neighborhood.

Hotels in Dennis Port

Ready to explore all that Dennis Port offers? First you'll need cozy place to get some shut-eye. Lock in one of the 16 accommodations close by and get your journey off to a sensational start.

Look into the deals on offer at the Bluegreen Vacations The Soundings, Ascend Resort Collection (79 Chase Avenue) and The Corsair & Cross Rip Oceanfront Resort (41 Chase Ave). They're our top picks.

Places to visit in Dennis Port

It's hard to picture how people once coped at home without all the gadgets we have these days. Take a look around Jericho House and Barn Museum and see how they did. Need more options? The intimacy and mastery of theater is difficult to ignore. Buy your tickets for a show at Cape Cod Theatre Company – Home of the Harwich Jr. Theatre to experience the magic for yourself!

Where do you fly into for Dennis Port?

Fasten your seatbelt, turn off your laptop and get ready to hit the tarmac at Barnstable Municipal Airport (HYA). Want some awesome news? You'll be just 8 miles (13 kilometers) to the west of Dennis Port.

Frequently asked questions

How much are vacation packages to Dennis Port?

You can score an amazing hotel and flight bundle from just CA $1,481. With one of our Travelocity vacation packages, a stay in Dennis Port has never looked so enticing! Save some time and money and then start packing that suitcase.

How long should my Dennis Port vacation be?

There are no firm rules when it comes to how long you should spend in Dennis Port, but the majority of people like to stay for around 3 nights. Got some leeway with your departure date? Consider booking another night or two. Then you'll have loads of time to check out the area's hidden treasures too.

Where can I get the best vacation package deals for Dennis Port?

Find your dream escape at Travelocity. With access to 400 airlines and a whopping 1,000,000 properties across the globe, finding the perfect Dennis Port package deal couldn't be simpler.

Why should I purchase my Dennis Port vacation bundle via Travelocity?

We have experiences and destinations for every kind of traveler, excellent service and 24/7 customer support. And to top it off, we'll match any better price you happen to find with our Price Match Guarantee.

Will I save money on my Dennis Port car rental if I bundle it with a hotel or flight?

Certainly — combine your car, hotel and flight into a Dennis Port vacation package and you can save a ton. With so much to see and do in and around Dennis Port, that rental car will make exploring easy. Once you've buckled yourself in, get out on the wide open road and find your way to Fenway Park, a must-see attraction around 113 kilometers from Dennis Port.

Which airport is best for Dennis Port?

Many fly into Martha's Vineyard Airport (MVY), 48 kilometers southwest of downtown Dennis Port. Others prefer Nantucket Memorial Airport (ACK) (48 kilometers away from central Dennis Port) or Provincetown Municipal Airport (PVC) (48 kilometers away from central Dennis Port).

What is there to do in Dennis Port?

Dennis Port is teeming with sights to discover, like Sea Street Beach and Cape Cod Theatre Company – Home of the Harwich Jr. Theatre. These two impressive attractions are on most people's travel itineraries.

Where should I stay when visiting Dennis Port?

If you're searching for a place to base yourself, take a look at the By The Sea Guests Bed And Breakfast And Suites. It's the top choice for many visitors.