Dennis Port Vacations from ￥155,890
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Dennis Port Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Iris Hotel Boston
Coolidge Corner
￥155,890
per person
Nov 19 - Nov 23
found 15 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
9.4/10 Exceptional! (656 reviews)
Clean, quiet and convenient location close to schools and the T. Staff were friendly and helpful and the breakfast was delicious. We had a great stay and would highly recommend. My only complaint is the $55 per night parking fee which we avoided by parking offsite.
Reviewed on Aug 25, 2026
YOTEL Boston
Seaport District
￥319,902
per person
Oct 1 - Oct 5
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
8.8/10 Excellent! (2,594 reviews)
Great location, walking distance to a lot. Only complaint was the bed was a little uncomfortable. Great stay otherwise.
Reviewed on Aug 24, 2026
Find the Best Dennis Port Vacation Packages
Dennis Port Beach Vacation
Forget the stresses of daily life and let your mind, body and soul unwind on your Dennis Port vacation. There's nothing more invigorating than a cool ocean breeze and the soothing melody of waves crashing onto the shore. Plan your trip to Dennis Port the easy way by choosing one of our Dennis Port vacation deals. Many people decide to spend their nights near Sea Street Beach, a local highlight just 0.80 kilometers from the city center.
Things You Should Know About Dennis Port
- Reserve a room in one of our Dennis Port beach hotels and experience this destination at its best. Wander along the water's edge and watch some stunning sunrises right outside your front door.
- Our private vacation homes, like The Corsair & Cross Rip Oceanfront Resort and Bluebird Dennisport, are popular with travelers of all sorts. Consider the amenities and get set for your stay in Dennis Port!
- Some 3,200 people live in Dennis Port. If you're after suggestions about what to see and do around these parts, why not start a conversation with one or two of the locals? Our Dennis Port things to do page is also a handy source of information.
- Sea Street Beach, Sea Street Beach and Cape Cod Theatre Company – Home of the Harwich Jr. Theatre are some great sights that should be on your travel agenda. With our Dennis Port vacation deals, you'll have more money in your back pocket to explore.
Dennis Port Hotel Deals
Holiday Hill Inn & Suites
352 Main Street Dennis Port MA
Fully refundableReserve now, pay when you stay
￥18,537
￥21,215 total
Aug 30 - Aug 31
includes taxes & fees
8.4/10 Very Good! (1,042 reviews)
"The rooms were alright, but for the price I feel you can stay somewhere else with more. It's great that they have all these other "amenities" like the ice cream stand and the games, but there's no discount or inclusion if you're staying at the inn. The ice cream is expensive, the arcade room is outdated ..."
Reviewed on Aug 24, 2026
The Corsair & Cross Rip Oceanfront Resort
41 Chase Ave Dennis Port MA
￥21,482
￥25,937 total
Sep 22 - Sep 23
includes taxes & fees
8.6/10 Excellent! (303 reviews)
"Not the cleanest room whatsoever. Poorly maintained, small rooms, small resort - there are plenty of option where you get way more for what you pay."
Reviewed on Aug 23, 2026
Bluebird Dennisport
426 Lower County Rd Dennis Port MA
￥30,526
￥38,575 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very Good! (270 reviews)
"The property has not been maintained at all. It's a good concept, but obviously very little follow-through and upkeep."
Reviewed on Aug 24, 2026
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.
Stay near popular Dennis Port attractions
Sea Street Beach
8.6/10 (122 reviews)
Sea Street Beach charms with warm Nantucket Sound waters and gentle surf perfect for families. Enjoy the picturesque jetties and lifeguarded swimming while the convenient snack bar keeps you refreshed.
Swan Pond River
8.4/10 (55 reviews)
This tranquil tidal estuary connects Swan Pond to Nantucket Sound with gentle waters perfect for kayaking. Paddle among reeds and diverse birdlife while enjoying the serene natural landscape away from coastal crowds.
Cape Cod Theatre Company – Home of the Harwich Jr. Theatre
7.6/10 (29 reviews)
Cape Cod Theatre Company stages multi-generational performances in an intimate, air-conditioned venue. Enjoy evening shows featuring both seasoned actors and emerging talents in this community-centered arts space.
Swan Pond
Commune with nature and explore the great outdoors at Swan Pond during your travels in Dennis Port. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.
Frequently asked questions
How much does a Dennis Port vacation package cost?
You'll find cheap prices from ￥155,890 on Expedia for your Dennis Port escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Dennis Port costs.
What are the cheapest months to go to Dennis Port?
If you're hoping to book a cheap Dennis Port vacation package, consider traveling in January, February and March. You'll typically find better rates on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Dennis Port?
Typically, a few days is ideal for a Dennis Port vacation. With a detailed itinerary, you can check out all the main attractions such as Swan Pond River, as well as discover some hidden gems along the way.
Is it worth booking a vacation package to Dennis Port?
Known for its watersports and home to popular attractions like Sea Street Beach, a Dennis Port vacation is bound to impress. Another top sight worth exploring? Don't miss Cape Cod Theatre Company – Home of the Harwich Jr. Theatre.
How to find the best Dennis Port package deals?
Bagging a cheap Dennis Port package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most affordable Dennis Port package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Dennis Port vacation as a package?
You can enjoy significant savings on your next Dennis Port break by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Dennis Port?
Enjoy amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Dennis Port adventure.
How to plan a trip to Dennis Port?
- Pick the ideal time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to go to Dennis Port.
- Set a budget: Factor in expenses such as flights, food and transportation when calculating how much to set aside for your trip to Dennis Port. Then, pick a hotel that matches your budget, whether that's an affordable option or a more upscale retreat.
- Work out your trip length: Consider how long you'd like to spend discovering Dennis Port. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Dennis Port vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
