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.
Lakeside Inn

Lakeside Inn

2 out of 5
per person
Oct 25 - Oct 31
found 4 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
7.4/10 Good! (2,171 reviews)
Staff was very friendly and room was clean. Bathroom was very outdated but clean

Reviewed on Aug. 4, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Friendly staff. Great location.

Reviewed on Aug. 10, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Oct 25 - Oct 31
found 4 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on Aug. 11, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
South End
per person
Oct 25 - Oct 31
found 4 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
8.8/10 Excellent! (968 reviews)
This was the single greatest stay of my life. The hotel is so cute and beautiful with lovely pineapple decor on the pillows, ceiling, and everywhere else (the attention to detail is superb) they offer you a complimentary drink upon check in, they provide you with a free metal recyclable water bottle, and a very comfortable and soft robe. However, The most important moment of my trip was the incredible house keeping staff! I was there to get married and couldn’t get dressed and leave until 3:30. Not only did the staff stay later to clean my room before I brought my bride back after the wedding, but they decorated the entire room with a sequined bed runner, balloons, confetti, decorations, and more. Every member of the front desk staff were so amazing and kind and helpful every step of the way! Thank you all so much from the bottom of my heart on behalf of myself and my bride!! She was so excited to enter the room and have one last wedding day surprise! We will be back (exclusively!) to the Pineapple! 🍍

Reviewed on Aug. 10, 2025

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
Fully refundableReserve now, pay when you stay
The price is CA $348 per night from Sep 8 to Sep 9
CA $348
CA $399 total
Sep 8 - Sep 9
includes taxes & fees
9.6/10 Exceptional! (160 reviews)
"They had goats in the back! I wish the fencing were more hand friendly and shirt friendly - I could lean over to pet. Breakfast was nourishing. and I could make tea in my room!"

Reviewed on Aug. 10, 2025

Sesuit Harbor House
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd, Hyannis, MA
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Sep 1 to Sep 2
CA $252
CA $367 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (264 reviews)
"Great place for kiddos! Rooms were clean and newly renovated. Water park was clean and fun with extended hours. My son was bummed he wasn’t allowed to use the hot tubs. Must be 14 years old."

Reviewed on Aug. 9, 2025

Margaritaville Resort Cape Cod
Hyannis Plaza Hotel

Hyannis Plaza Hotel

2.5 out of 5
662 Main Street, Hyannis, MA
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Sep 10 to Sep 11
CA $112
CA $143 total
Sep 10 - Sep 11
includes taxes & fees
6.8/10 (834 reviews)
"Nice place, small swimming pool, cant go outside unless u exit the building"

Reviewed on Aug. 8, 2025

Hyannis Plaza Hotel
See all 6,157 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.
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Beach Vacations
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Discover the most popular places to visit in Dennis

Mayflower Beach

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.

Mayflower Beach

What to do in Dennis

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

CA $69
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Cape Cod Self-Guided Driving Audio Tour

Cape Cod Self-Guided Driving Audio Tour

CA $23
per traveller
100% of travellers recommend
Cape Cod Self-Guided Driving Audio Tour
Cape Cod and Provincetown Scenic Self-Guided Driving Audio Tour

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

CA $34
per traveller
80% of travellers recommend
Cape Cod & Provincetown: Self-Guided Drive & Walk 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 $619 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.

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