Dennis Port Vacation Packages 2026 from $419

Dennis Port flight + hotel vacation packages

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

The Westin Waltham-Boston

Save 100% on your flight

$419

per person

Jul 3 - Jul 5

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

D. Hotel Suites & Spa

Save 100% on your flight

$561

per person

Jun 21 - Jun 26

found 5 hours ago

Roundtrip flight included

Minneapolis (MSP) to Boston (BOS)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. You'll appreciate the gym, bar/lounge, and laundry facilities.

The Langham, Boston

Downtown Boston

Save 100% on your flight

$927

per person

Jul 3 - Jul 6

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.

Sea Crest Beach Resort

Save 100% on your flight

$707

per person

Jun 3 - Jun 8

found 5 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

A private beach, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the picnic area.

The Newbury Boston

Back Bay

Save 100% on your flight

$2,845

per person

Jun 6 - Jun 13

found 24 hours ago

Roundtrip flight included

Charlotte (CLT) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.

Top Dennis Port hotels deals

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

The Corsair & Cross Rip Oceanfront Resort

41 Chase Ave Dennis Port MA

$134 nightly

$152 total

Apr 15 - Apr 16

Total with taxes and fees

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

Holiday Hill Inn & Suites

352 Main Street Dennis Port MA

$113 nightly

$129 total

May 10 - May 11

Total with taxes and fees

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

Bluegreen Vacations The Soundings, an Ascend Collection Resort

79 Chase Avenue Dennis Port MA

Get rates

This hotel features an indoor pool and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, express check-out, and laundry facilities are also on offer.

Pool

Parking included

Bluegreen Vacations The Breakers Resort, an Ascend Collection Resort

61 Chase Ave Dennis Port MA

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

On private beach

Pool

Sea Shell Motel

45 Chase Avenue Dennis Port MA

$159 nightly

$181 total

May 7 - May 8

Total with taxes and fees

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

Dane Street Beach at Mackerel Cove aerial view panorama in city of Beverly, Massachusetts MA, USA.

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.

Mute Swan at the Cape Cod National Seashore in Eastham

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.

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 waterfront 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 $419. 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.