Dennis Vacation Packages

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Your Dennis Vacation

Come and experience this wonderful city for yourself with a Dennis vacation package. Consider spending a few days in the neighborhood of Northwest Harwich, which is good for nature and walking, and your time here is bound to be unforgettable. If taking in sights is part of the plan during your trip to Dennis, visit major attractions like Cape Cod Museum of Art, Cape Cod Museum of Natural History and Mayflower Beach. Your dream Dennis vacation is a few clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your style.

Top Dennis Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,931, price is now CA $816 per person
CA $816
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,196, price is now CA $1,272 per person
CA $1,272
per person
Jan 21 - Jan 24
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $1,982, price is now CA $1,354 per person
CA $1,354
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (1,354 reviews)

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Lexington Green Historic District
Save 100% on your flight
Price was CA $1,638, price is now CA $1,125 per person
CA $1,125
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (268 reviews)
Gorgeous and cosy with great breakfast

Reviewed on Oct 22, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,424, price is now CA $1,664 per person
CA $1,664
per person
Dec 30 - Jan 2
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)

Dennis Beach Vacation

There's nothing more relaxing than a Dennis vacation. Whether you're treating yourself to refreshing cocktails at a local bar or flipping through a magazine along the water's edge, your trip to Dennis is the time to live out your beachy daydreams. Many visitors will tell you to stay near Mayflower Beach, situated just 2 kilometres from the centre of town. However, you'll also discover an excellent range of Dennis vacation packages around Corporation Beach and Bayview Beach, two other well-liked nearby options.

Things You Should Know About Dennis

  • If your idea of a perfect escape is fresh sea air and water views, check out our Dennis beach hotels. You're sure to forget the pressures of daily life at these blissful beachy retreats.
  • Alternatively, check out our range of private vacation homes. They're popular with travellers planning a vacation in Dennis. Begin your search with Sesuit Harbour House and Starlight Lodge Cape Cod.
  • Our Dennis things to do page is an excellent place to discover fun activities around here. Of course, it's hard to beat a little local knowledge. With a population of 6,096 cm Dennis, we're sure you'll find a few friendly people willing to give you some tips.
  • Dennis vacation deals are an excellent way to save on exciting experiences. Some ideas, such as Mayflower Beach, Mayflower Beach and Corporation Beach, should be at the top of your sightseeing list.

Ready to book your vacation to Dennis?

 

Choose your dates

Dennis Hotel Deals

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
1421 Main Street Dennis MA
The price is CA $471 per night from Oct 31 to Nov 1
CA $471
CA $539 total
Oct 31 - Nov 1
includes taxes & fees
9.6/10 Exceptional! (218 reviews)
"Very welcoming and helpful staff. Room was ideal and we loved the fire pit."

Reviewed on Oct 17, 2026

Sesuit Harbor House
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is CA $493 per night from Nov 29 to Nov 30
CA $493
CA $564 total
Nov 29 - Nov 30
includes taxes & fees
Chatham Bars Inn
Hyannis Travel Inn

Hyannis Travel Inn

2.5 out of 5
18 North St Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Nov 4 to Nov 5
CA $138
CA $158 total
Nov 4 - Nov 5
includes taxes & fees
9.6/10 Exceptional! (1,028 reviews)
"N/a"

Reviewed on Oct 29, 2026

Hyannis Travel Inn
See all 5,898 properties in Dennis
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Dennis attractions

A sunset over a snow-covered beach with dunes and grasses.
Photo by Elizabeth Sanders
Open Photo by Elizabeth Sanders

Mayflower Beach

9.2/10 (224 reviews)
Why not spend a carefree afternoon at Mayflower Beach during your travels in Dennis? While you're in the area, stroll along the waterfront.
See properties

What to do in Dennis

Cape Cod and Provincetown Scenic Self-Guided Driving Audio Tour

Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour

CA $36
per traveller
Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)

CA $71
per adult
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
Cape Cod & Provincetown Self-Guided Driving & Walking Audio Tour

Cape Cod & Provincetown Self-Guided Driving & Walking Audio Tour

CA $36
per traveller
Cape Cod & Provincetown Self-Guided Driving & Walking Audio Tour
See all activities in Dennis

Frequently asked questions

How much does a Dennis vacation package cost?
You can snap up a vacation package to this destination from CA $816 on Expedia. However, how much your vacation to Dennis costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Dennis?
The off-season is the best time to travel to Dennis if you're trying to save. Another tip for scoring cheap Dennis vacation packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Dennis?
Dennis vacations can be as short or long as you like, but to get a true feel for this destination, we reckon 3 days is about right. In this timeframe, you can fit in top attractions like Cape Cod Rail Trail and Corporation Beach as well as lesser-known gems. Don't miss out on neighbourhoods such as Bass River and Northwest Harwich either. If you plan wisely, you can even schedule a day trip or two from Dennis too.
Is it worth booking a vacation package to Dennis?
Whether you're planning to check out attractions like Mayflower Beach and Corporation Beach, or want to experience its top-notch walking trails and coastal beaches, a Dennis vacation is sure to exceed your expectations. Book your trip with Expedia and discover why Dennis is such a good vacation destination.
How to find the best Dennis package deals?
Finding a cheap Dennis package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Dennis package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Dennis vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still have the freedom to create a customized Dennis vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Dennis?
If you have your Dennis vacation dates locked in, book as soon as you can to grab some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Dennis?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Dennis.
  2. Budget wisely: On top of the price of your accommodations, you'll need to factor in other expenses too. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Dennis.
  3. Decide how long to go for: Now that you're up to speed on Dennis, you can work out the perfect length of your vacation. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: Once you've settled on your dates and duration, lock in the right Dennis vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.