Dennis Port Vacation Packages 2026 from $699

Dennis Port flight + hotel vacation packages

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

Boston Lodge and Suites

Dorchester

$699

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

Boston Harbor Hotel

North End

$1,012

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

Luxury Apartments by Hyatus at Boston Everett

$856

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Boston (BOS)

This apartment features a gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the a rooftop terrace and perks like free self parking.

Furnished Apartment Near Longwood

North Brookline

Save 100% on your flight

$1,896

per person

Sep 23 - Sep 30

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to Boston (BOS)

This apartment features a virtual front desk. Take advantage of the self parking.

The Charles Hotel

West Cambridge

Save 100% on your flight

$804

per person

Oct 29 - Nov 1

found 21 hours ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

A full-service spa, 3 restaurants, and a 24-hour gym are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.

Top Dennis Port hotels deals

Holiday Hill Inn & Suites

352 Main Street Dennis Port MA

$118 nightly

$135 total

Sep 1 - Sep 2

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.

The Corsair & Cross Rip Oceanfront Resort

41 Chase Ave Dennis Port MA

$237 nightly

$269 total

Sep 9 - Sep 10

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.

Bluebird Dennisport

426 Lower County Rd Dennis Port MA

Free Cancellation

Reserve now, pay when you stay

$224 nightly

$256 total

Aug 27 - Aug 28

Total with taxes and fees

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

Dennis Port Surf Club (Boutique Hotel)

329 Main Street Dennis Port MA

Free Cancellation

Reserve now, pay when you stay

$224 nightly

$257 total

Aug 26 - Aug 27

Total with taxes and fees

This motel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop and a picnic area are also provided.

By the Sea Guests Bed & Breakfast & Suites

57 Chase Avenue & Inman Road Extension Dennis Port MA

Get rates

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Kingfisher Oceanside

15 Sea St Dennis Port MA

$160 nightly

$184 total

Sep 9 - Sep 10

Total with taxes and fees

A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A garden, a picnic area, and express check-out are also on offer.

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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.

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Frequently asked questions

How much are vacation packages to Dennis Port?

You can score an amazing hotel and flight bundle from just $699. 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.