Great Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Great Island

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,556, price is now CA $1,032 per person
CA $1,032
per person
Jan 31 - Feb 3
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,120, price is now CA $1,142 per person
CA $1,142
per person
Jan 31 - Feb 3
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
!

Reviewed on Nov 10, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,360, price is now CA $1,524 per person
CA $1,524
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)
The best location and the beat service! The best swimming pool

Reviewed on Nov 9, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,311, price is now CA $1,580 per person
CA $1,580
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,803, price is now CA $1,283 per person
CA $1,283
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

Great Island Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is CA $498 per night from Nov 12 to Nov 13
CA $498
CA $570 total
Nov 12 - Nov 13
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
Inn on the Square

Inn on the Square

3.5 out of 5
40 North Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Nov 15 to Nov 16
CA $199
CA $263 total
Nov 15 - Nov 16
includes taxes & fees
Inn on the Square
Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

3 out of 5
867 Iyannough Road Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Nov 17 to Nov 18
CA $179
CA $205 total
Nov 17 - Nov 18
includes taxes & fees
8.8/10 Excellent! (762 reviews)
"We stayed two nights and our stay was excellent. The hotel is very clean and bright, our room was very pleasant and a nice size. We had plenty of room for all our stuff and the bed was quite comfortable. The bathroom was roomy and the shower was excellent! Breakfast was pretty much the regular hotel ..."

Reviewed on Nov 9, 2026

Fairfield Inn & Suites by Marriott Cape Cod Hyannis
See all 5,571 properties in Great Island
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

Frequently asked questions

How much does a Great Island vacation package cost?
We make it easy to travel somewhere new, with Great Island packages starting from just CA $1,032. You'll have the flexibility to combine your preferred airlines, hotels and car rental. For the ultimate escape, why not add a few tours and experiences to your travel itinerary?
How do I get a cheap travel package to Great Island?
Combine your hotels and flights, add extras such as activities, and save with a Great Island vacation package. You won't just pick up big discounts on your adventure — you'll have a world of choice at your fingertips too. When you book with Expedia, you'll have your pick of over 550 airlines and 1,000,000 properties around the globe. Your next grand adventure starts right here, right now!
Where should I stay in Great Island?
With lots to explore in Great Island, we recommend you lock in a hotel close to its attractions. Cape Cod Inflatable Park, Seagull Beach and Whydah Pirate Museum are some fascinating ones to add to your itinerary.
How far in advance should I book my Great Island vacation?
The earlier you book, the better. Airlines usually release flights up to 12 months ahead of departure, and this is your chance to pick up some rock-bottom prices. Boss just told you to use up your vacation time next month? That's fine too — Expedia are never short of fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Great Island travel package include?
From airfares and hotels to rental cars, Expedia can help you craft a Great Island package that suits you. Heading away for a while? Consider a flight, rental car and hotel bundle. If you're taking a short break, an airfare and hotel deal may be more your style. Tours and activities can be added once you've made your booking. Our vacation packages make it a breeze to plan and save.
What should I know before booking a Great Island travel package?
Whether it's adventure or relaxation you're after, a Great Island vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Great Island Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You get to choose. We have more than 550 partner airlines around the world, so you have options galore when arranging your Great Island trip.
If I'm not able to travel, can I cancel my Great Island vacation package?
Plans can change in a flash, so yes. You may be able to amend or cancel your Great Island vacation package for free within 24 hours of booking. For older bookings, you can still cancel and rebook, but your car rental company, airline or hotel may impose a fee. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Things to do

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)
Self Guided Driving Audio Tour Cape Cod

Self Guided Driving Audio Tour Cape Cod

CA $24
per traveller
Self Guided Driving Audio Tour Cape Cod
See all activities in West Yarmouth
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.