West Dennis Vacations from ￥286,222

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The Latest West Dennis Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was ￥329,192, price is now ￥286,222 per person
￥286,222
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9/10 Wonderful! (3,501 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was ￥690,242, price is now ￥512,846 per person
￥512,846
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ￥608,448, price is now ￥454,508 per person
￥454,508
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was ￥366,275, price is now ￥292,425 per person
￥292,425
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (1,636 reviews)

Omni Parker House

Omni Parker House

4.5 out of 5
Downtown Boston
Price was ￥350,400, price is now ￥310,480 per person
￥310,480
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9/10 Wonderful! (3,731 reviews)
This property is beautiful and within walking distance of everything!

Reviewed on Nov 7, 2026

Find the Best West Dennis Vacation Packages

West Dennis Beach Vacation

Live out your beach fantasies on your West Dennis vacation. Enjoy a refreshing walk, savor the sweeping coastal vistas and collect pretty seashells during your trip to West Dennis. Situated just 2 kilometers from the center of town, West Dennis Beach is the place to be for many travelers. Look through our West Dennis vacation packages and watch your travel budget stretch further!

West Dennis Hotel Deals

Lighthouse Inn

Lighthouse Inn

3 out of 5
1 Lighthouse Inn Rd West Dennis MA
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Lighthouse Inn
Travelodge by Wyndham Cape Cod Area

Travelodge by Wyndham Cape Cod Area

2 out of 5
99 Main St West Dennis MA
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Travelodge by Wyndham Cape Cod Area
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is ￥55,904 per night from Nov 8 to Nov 9
￥55,904
￥63,981 total
Nov 8 - Nov 9
includes taxes & fees
9.2/10 Wonderful! (876 reviews)
"Amazing place to stay. Can't wait to go back."

Reviewed on Oct 30, 2026

Chatham Bars Inn
See all 5,344 properties in West 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.

Stay near popular West Dennis attractions

A sandy path with wooden posts and a rope fence leading to the ocean.

West Dennis Beach

9.2/10 (289 reviews)
This two-mile stretch along Nantucket Sound offers warm, calm waters perfect for windsurfing and swimming. Spread out on the uncrowded sandy shore with easy access to the beachfront snack bar and playground.
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What to do in West Dennis

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

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

￥7,835
per adult
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
Private Hyannis Walking Food Tour with Local Tastings

Private Hyannis Walking Food Tour with Local Tastings

￥50,154
per adult
Private Hyannis Walking Food Tour with Local Tastings
See all activities in West Dennis

Frequently asked questions

How much does a West Dennis vacation package cost?
Offering excellent value package deals from ￥286,222 on Expedia, you'll be surprised at how little a vacation to West Dennis costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to West Dennis?
To pick up cheap West Dennis vacation packages, organize your trip outside of busy periods such as school holidays. You'll generally find better availability and lower prices when it's less busy.
How many days is enough for West Dennis?
With around 2 days, you'll have plenty of time to experience popular neighborhoods such as Bass River and Northwest Harwich during your West Dennis vacation. Remember to also add Bass River Lighthouse and Jericho House and Barn Museum to your must-see list. Searching for more adventures? Consider venturing outside of West Dennis on tours and day trips.
Is it worth booking a vacation package to West Dennis?
It's easy to see why a West Dennis vacation is on the to-do list of many travelers. Top attractions like Bass River Lighthouse are just the beginning of things to keep you busy here.
How to find the best West Dennis package deals?
Landing a cheap West Dennis package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly West Dennis package deals. Want a simple trick to score the biggest 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 West Dennis vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging stays and flights individually. Better still, you can personalize your West Dennis getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to West Dennis?
If you have your West Dennis travel dates locked in, book as soon as you can to score some unbeatable 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 great for traveling on a whim.
How to plan a trip to West Dennis?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the activities available will also help you decide when to escape to West Dennis.
  2. Budget wisely: In addition to the price of your stay, you'll need to factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that may come up during your trip to West Dennis.
  3. Decide your trip length: Consider how long you want to spend exploring West Dennis. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized West Dennis vacation package.

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