Dennis Port Vacation Packages 2025/2026 from $240

Dennis Port flight + hotel vacation packages

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

InnSeason Resorts Surfside

Save 100% on your flight

per person

Oct 31 - Nov 3

found 3 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

This hotel features an indoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.

The Revolution Hotel

South End

Save 100% on your flight

per person

Nov 8 - Nov 11

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.

DoubleTree by Hilton Boston North Shore

Save 100% on your flight

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Chicago (CHI) 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.

The Beverly

Save 100% on your flight

per person

Oct 24 - Oct 27

found 17 hours ago

Roundtrip flight included

Chicago (CHI) 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 Westin Boston Seaport District

Seaport District

Save 100% on your flight

per person

Nov 8 - Nov 11

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

The hotel's indoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the restaurant, hot tub, and laundry facilities.

Top Dennis Port hotels deals

Holiday Hill Inn & Suites

352 Main Street, Dennis Port, MA

$119 nightly

$136 total

Sep 1 - Sep 2

Total includes 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.

Bluebird Dennisport

426 Lower County Rd, Dennis Port, MA

$159 nightly

$180 total

Sep 8 - Sep 9

Total includes 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.

Oceanside Motel

329 Main Street, Dennis Port, MA

$79 nightly

$90 total

Aug 24 - Aug 25

Total includes taxes and fees

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.

Kingfisher Oceanside

15 Sea St, Dennis Port, MA

$236 nightly

$271 total

Sep 1 - Sep 2

Total includes 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.

The Corsair & Cross Rip Oceanfront Resort

41 Chase Ave, Dennis Port, MA

$169 nightly

$192 total

Sep 10 - Sep 11

Total includes 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.

Edgewater Beach Resort, a VRI resort

95 Chase Avenue, Dennis Port, MA

$232 nightly

$266 total

Sep 10 - Sep 11

Total includes taxes and fees

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.

Don't see what you're looking for?

See all available properties in Dennis Port

View all properties

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

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 seaside 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 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 $240. 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.