Dennis Vacation Packages 2026 from $344

Dennis flight + hotel vacation packages

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

D. Hotel Suites & Spa

$344

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) 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.

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$842

per person

Apr 7 - Apr 11

found 13 hours ago

Roundtrip flight included

Los Angeles (LAX) 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

$1,304

per person

Apr 23 - Apr 26

found 1 day ago

Roundtrip non-stop flight included

Las Vegas (LAS) 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.

Found Hotel Boston Common

Bay Village

$637

per person

Mar 26 - Mar 30

found 9 hours ago

Roundtrip non-stop flight included

Columbus (CMH) to Boston (BOS)

Free WiFi in public areas, luggage storage, and a safe deposit box are available at this hotel. There's locker space and multilingual staff can provide around-the-clock assistance.

Raffles Boston

Back Bay

Save 100% on your flight

$1,648

per person

Mar 26 - Mar 30

found 9 hours ago

Roundtrip non-stop flight included

Columbus (CMH) to Boston (BOS)

A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.

Top Dennis hotels deals

MAYFLOWER BEACH! Waterview Home with Central A/C Across from Mayflower Beach

Dennis MA

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This vacation home features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.

Kitchen

Washer

Mermaid Cottage! beautiful propety!

Dennis MA

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This cottage features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$208 nightly

$238 total

Feb 12 - Feb 13

Total with taxes and fees

This smoke-free resort features a full-service spa, a water park, and 2 restaurants. There's fun for all ages with a lazy river and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the outdoor pool and perks like free self parking and free WiFi.

Pool

Hot Tub

Chatham Bars Inn

297 Shore Rd Chatham MA

$364 nightly

$417 total

Feb 5 - Feb 6

Total with taxes and fees

A private beach, a full-service spa, and 3 outdoor tennis courts are all featured at this luxury resort. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free valet parking and a free beach shuttle.

On private beach

Pool

Chatham Wayside Inn

512 Main St Chatham MA

Free Cancellation

Reserve now, pay when you stay

$172 nightly

$197 total

Feb 23 - Feb 24

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

Pool

Breakfast included

The Corsair & Cross Rip Oceanfront Resort

41 Chase Ave Dennis Port MA

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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

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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

Mayflower Beach

Why not spend a carefree afternoon at Mayflower Beach during your travels in Dennis? While you're in the area, stroll along the waterfront.

Corporation Beach

If a restful vacation is part of your travel plans, Corporation Beach might be the perfect place to seek out during your trip to Dennis. While you're in the area, stroll along the waterfront.

Theater actors in costumes play in the play

Cape Playhouse

You can make plans for a show at Cape Playhouse during your stay in Dennis. Stroll along the beautiful beaches or attend a sporting event in this family-friendly area.

Frequently asked questions

How much are vacation packages to Dennis?

You can pick up an excellent hotel and flight bundle for as low as $344. With a Travelocity vacation package, a trip to Dennis has never been more tempting! Save both time and money and then get a start on packing those bags.

How long should my Dennis vacation be?

If you need some guidance, most visitors spend about 3 nights vacationing in Dennis. But to discover the true spirit of this destination, stay a bit longer. That way you can see more and really experience the local vibe.

Where can I get the best vacation package deals for Dennis?

You'll come across a fantastic range of Dennis package deals on Travelocity. With no less than 400 airlines and 1,000,000 worldwide properties, arranging a dream vacation will be a piece of cake.

Why should I book my Dennis vacation bundle via Travelocity?

By booking your flights, hotel, activities and car rental altogether, you'll save time and money. We offer a dedicated team of experts available 24/7, and you'll know that you'll always be getting the best deal possible with our Price Match Guarantee. So, what's stopping you? Book the vacation of your dreams today and start packing!

Can I save money on my Dennis car rental if I book it with a hotel or flight?

You certainly can — bundle your car, hotel and flight into a Dennis vacation package and you can save a tidy sum. With so many things to do in Dennis, that rental car will make exploring easy. Once you've settled into the driver's seat, hit the wide open road and head toward Fenway Park, a must-see sight about 65 mi from Dennis.

Which airport is best for Dennis?

Logan Intl. Airport (BOS) is a main hub. You'll find it roughly 60 mi northwest of Dennis. Your other options are Martha's Vineyard Airport (MVY) (30 mi away from central Dennis) and Nantucket Memorial Airport (ACK) (35 mi away from central Dennis).

What is there to do in Dennis?

You'll notice an undeniable magic as you stroll through the streets of Dennis. Cape Cod Museum of Art and Corporation Beach are just a couple of landmarks that make this city such a sought-after destination, so put them on your itinerary.

Where should I stay when visiting Dennis?

The Isaiah Hall Bed And Breakfast Inn is the top choice of many travelers. Book now to avoid missing out.