Dennis Vacation Packages 2026 from $359

Dennis flight + hotel vacation packages

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

The Cove at Yarmouth by Westgate Resorts

Save 100% on your flight

$359

per person

May 2 - May 5

found 10 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free aparthotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Boston Harbor Hotel

North End

Save 100% on your flight

$2,049

per person

Jun 8 - Jun 12

found 1 day ago

Roundtrip flight included

Denver (DEN) 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.

The Westin Waltham-Boston

Save 100% on your flight

$1,507

per person

Jun 13 - Jun 19

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Omni Boston Hotel at the Seaport

Seaport District

Save 100% on your flight

$1,616

per person

May 31 - Jun 5

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

A full-service spa, 4 restaurants, and an outdoor pool are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, poolside bar, and snack bar/deli.

Eurostars The Boxer

West End

Save 100% on your flight

$947

per person

Jun 8 - Jun 12

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. A computer station, dry cleaning, and luggage storage are also on offer.

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.

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$204 nightly

$234 total

Apr 1 - Apr 2

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.

Bayside Resort Hotel

225 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$141 total

Apr 12 - Apr 13

Total with taxes and fees

This hotel features 2 poolside bars, 2 bars/lounges, and an indoor pool. Enjoy the gym and free perks like buffet breakfast and free self parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.

Aiden by Best Western Cape Cod - West Yarmouth

476 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$116 total

Apr 5 - Apr 6

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the 24-hour gym and perks like free self parking.

Chatham Bars Inn

297 Shore Rd Chatham MA

$368 nightly

$421 total

Apr 1 - Apr 2

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.

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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 seaside 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 $359. 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.