West Dennis Vacation Packages

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Your West Dennis Vacation

Experience the unique personality of West Dennis with a tailor-made West Dennis vacation package. From its family-friendly attractions to its laid-back lifestyle and beyond, you'll never have a dull moment in this city. Every trip to West Dennis needs a well-planned itinerary. Fill yours with famous sights like Cape Cod Museum of Art, Hyannis Harbor and Mayflower Beach. Don't delay exploring this city any longer. Your perfect West Dennis vacation is just a few clicks away with Expedia.

Top West Dennis Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was CA $1,424, price is now CA $942 per person
CA $942
per person
Mar 21 - Mar 25
found 11 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..

Reviewed on Feb 2, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,176, price is now CA $2,251 per person
CA $2,251
per person
Apr 27 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $3,542, price is now CA $2,391 per person
CA $2,391
per person
Apr 27 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you

Reviewed on Feb 3, 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was CA $1,818, price is now CA $1,254 per person
CA $1,254
per person
Mar 21 - Mar 25
found 11 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Excellent property conveniently located in Beacon Hill. Rooms are a tad on the small side but well appointed and clean.

Reviewed on Feb 7, 2026

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Price was CA $1,434, price is now CA $991 per person
CA $991
per person
Apr 27 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,215 reviews)
Great room, wonderful friendly customer service

Reviewed on Feb 8, 2026

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 kilometres 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!

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West Dennis Hotel Deals

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 $218 per night from Feb 12 to Feb 13
CA $218
CA $328 total
Feb 12 - Feb 13
includes taxes & fees
8.6/10 Excellent! (441 reviews)
Clean room, nice staff, the only problem was the internet was slow

Reviewed on Feb 2, 2026

Margaritaville Resort Cape Cod
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is CA $494 per night from Feb 12 to Feb 13
CA $494
CA $565 total
Feb 12 - Feb 13
includes taxes & fees
9.2/10 Wonderful! (808 reviews)
Beautiful property

Reviewed on Jan 24, 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Feb 11 to Feb 12
CA $182
CA $267 total
Feb 11 - Feb 12
includes taxes & fees
9.2/10 Wonderful! (630 reviews)
Courteous staff, helpful with dining suggestions. Loved the room. Very comfortable bed, warm and cozy.

Reviewed on Jan 29, 2026

Chatham Wayside Inn
See all 5,411 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in West Dennis

West Dennis Beach which includes a beach as well as a small group of people

West Dennis Beach

One of the most popular beaches in Dennis, this part of Cape Cod is vast and has the perfect weather for a range of land-based and offshore activities.

West Dennis Beach
Bass River Lighthouse featuring a house and a lighthouse

Bass River Lighthouse

Many people visit this historical lighthouse for its lore. It is also a wonderful place to enjoy a walk.

Bass River Lighthouse

What to do in West Dennis

Cape Cod and Provincetown Scenic Self-Guided Driving Audio Tour

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

CA $34
per traveller
Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour
Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

CA $68
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
See all activities in West Dennis

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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.