Dennis Port Vacation Packages 2025/2026 from $555

Dennis Port flight + hotel vacation packages

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

DoubleTree by Hilton Boston North Shore

per person

Aug 26 - Aug 31

found 5 hours ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

This hotel features 2 restaurants, an indoor pool, and a gym. Families will appreciate the arcade/game room and convenience store. Enjoy the sauna and perks like free self parking.

Raffles Boston

Back Bay

Save 100% on your flight

per person

Sep 23 - Sep 30

found 19 hours ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.

The Inn at Hastings Park, Relais & Chateaux - Boston

Save 100% on your flight

per person

Aug 13 - Aug 18

found 20 hours ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.

The Beverly

Save 100% on your flight

per person

Aug 13 - Aug 18

found 21 hours ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-in. Express check-out and a virtual front desk are also provided.

The Club at New Seabury

Save 100% on your flight

per person

Aug 25 - Aug 29

found 22 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Boston (BOS)

A golf course, 2 restaurants, and 15 outdoor tennis courts are all featured at this smoke-free condo resort. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas. Enjoy the gym and unwind at the bar/lounge and beach bar.

Top Dennis Port hotels deals

Holiday Hill Inn & Suites

352 Main Street, Dennis Port, MA

Free Cancellation

Reserve now, pay when you stay

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This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. There's fun for all ages with mini golf and an arcade/game room, and supervised childcare is an added bonus. There's a seasonal outdoor pool on site, and a 24-hour front desk and a snack bar/deli are also provided.

Pool

Parking included

The Corsair & Cross Rip Oceanfront Resort

41 Chase Ave, Dennis Port, MA

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This hotel's private beach, 2 outdoor pools, and 2 hot tubs are some of the highlights. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the indoor pool and perks like free self parking and free WiFi.

On private beach

Pool

Bluebird Dennisport

426 Lower County Rd, Dennis Port, MA

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This hotel features an indoor pool and a seasonal outdoor pool. WiFi in public areas is free. Luggage storage is also provided.

Pool

Pet friendly

Oceanside Motel

329 Main Street, Dennis Port, MA

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An outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area is also provided.

Pool

Parking included

Edgewater Beach Resort, a VRI resort

95 Chase Avenue, Dennis Port, MA

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A private beach and an outdoor pool are featured at this smoke-free aparthotel. Enjoy the indoor pool and perks like free self parking and free WiFi. There's a gym on site, and laundry facilities and concierge services are also offered.

Pool

Kitchen

Sea Shell Motel

45 Chase Avenue, Dennis Port, MA

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This motel features a picnic area, concierge services, and free self parking. Enjoy the free continental breakfast each morning. Express check-in, express check-out, and barbecue grills are also on offer.

On private beach

Breakfast included

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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.

Popular places to visit

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.

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

5/5(1 review)

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

Swan Pond River

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.

Frequently asked questions

How much are vacation packages to Dennis Port?

You can score an amazing hotel and flight bundle from just $555. 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 70 mi from Dennis Port.

Which airport is best for Dennis Port?

Many fly into Martha's Vineyard Airport (MVY), 30 mi southwest of downtown Dennis Port. Others prefer Nantucket Memorial Airport (ACK) (30 mi away from central Dennis Port) or Provincetown Municipal Airport (PVC) (30 mi 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.