Dennis Port Vacation Packages 2026 from $439

Dennis Port flight + hotel vacation packages

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

The Wylie Inn and Conference Center at Endicott College

Save 100% on your flight

$439

per person

Sep 15 - Sep 19

found 24 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

A 24-hour gym, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A coffee shop, a computer station, and luggage storage are also on offer.

Boston Harbor Hotel

North End

Save 100% on your flight

$1,084

per person

Aug 27 - Aug 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

By the Sea Guests Bed & Breakfast & Suites

Save 100% on your flight

$815

per person

Aug 27 - Aug 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

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.

Beachside Village Resort

Save 100% on your flight

$744

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Austin (AUS) to Boston (BOS)

A seasonal outdoor pool is featured at this apartment, along with free WiFi in public areas and express check-out. Laundry facilities, barbecue grills, and a virtual front desk are also on offer.

Nantucket Inn

Save 100% on your flight

$1,358

per person

Aug 27 - Aug 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

2 outdoor tennis courts, 2 hot tubs, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.

Top Dennis Port hotels deals

Holiday Hill Inn & Suites

352 Main Street Dennis Port MA

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$174 total

Aug 2 - Aug 3

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

The Corsair & Cross Rip Oceanfront Resort

41 Chase Ave Dennis Port MA

$288 nightly

$328 total

Jul 26 - Jul 27

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

Bluebird Dennisport

426 Lower County Rd Dennis Port MA

Free Cancellation

Reserve now, pay when you stay

$240 nightly

$275 total

Jul 21 - Jul 22

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.

Pool

Pet friendly

Dennis Port Surf Club (Boutique Hotel)

329 Main Street Dennis Port MA

Free Cancellation

Reserve now, pay when you stay

$310 nightly

$355 total

Aug 9 - Aug 10

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.

Pool

Pet friendly

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.

On private beach

Parking included

Kingfisher Oceanside

15 Sea St Dennis Port MA

$305 nightly

$349 total

Jul 15 - Jul 16

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.

Pool

Parking 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.

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

Frequently asked questions

How much are vacation packages to Dennis Port?

You can score an amazing hotel and flight bundle from just $439. 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.