Dennis Port Vacation Packages 2025/2026 from $350

Dennis Port flight + hotel vacation packages

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

Eurostars The Boxer

West End

Save 100% on your flight

$350

per person

Nov 8 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Business travelers can take advantage of the business center. A computer station, dry cleaning, and luggage storage are also on offer.

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$499

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip 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

Save 100% on your flight

$1,007

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Lakeside Inn

$461

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Boston (BOS)

This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

The Merchant

Downtown Salem

Save 100% on your flight

$2,785

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

This hotel features free WiFi in public areas, concierge services, and self parking. Enjoy the free on-the-go breakfast each morning. A terrace, a lobby fireplace, and a communal living room are also on offer.

Top Dennis Port hotels deals

Holiday Hill Inn & Suites

352 Main Street, Dennis Port, MA

$113 nightly

$130 total

Oct 5 - Oct 6

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

$149 nightly

$169 total

Oct 5 - Oct 6

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

Edgewater Beach Resort, a VRI resort

95 Chase Avenue, Dennis Port, MA

$220 nightly

$252 total

Oct 23 - Oct 24

Total with 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.

Pool

Kitchen

Bluebird Dennisport

426 Lower County Rd, Dennis Port, MA

$159 nightly

$179 total

Oct 5 - Oct 6

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

Oceanside Motel

329 Main Street, Dennis Port, MA

Get rates

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

Kingfisher Oceanside

15 Sea St, Dennis Port, MA

$186 nightly

$213 total

Oct 5 - Oct 6

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.

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 waterfront 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 $350. 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.