Hamilton 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

Your Hamilton Vacation

Book a tailored Hamilton vacation package that has everything you need and no unnecessary extras. Good for walking, nature and views, consider staying in the neighborhood of Great Neck. During your trip to Hamilton, carve some time in your schedule for sightseeing. A popular place to start exploring is Appleton Farms Grass Rides. Stop daydreaming and start doing. Check out the broad range of options on Expedia today and finally put your Hamilton vacation plans into action!

Top Holiday Package Deals in Hamilton

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,411, price is now CA $706 per person
CA $706
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was CA $1,947, price is now CA $1,249 per person
CA $1,249
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,397, price is now CA $1,548 per person
CA $1,548
per person
Jan 29 - Feb 1
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,234, price is now CA $1,488 per person
CA $1,488
per person
Jan 14 - Jan 17
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
The only place I’ll stay in Boston

Reviewed on Nov 7, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,542, price is now CA $1,098 per person
CA $1,098
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
Coffee machine in our room did not work and unfortunately our room located near the stair exit was not the most quiet. Other than that, was a very nice hotel with lovely staff.

Reviewed on Nov 7, 2026

Hamilton Hotel Deals

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
The price is CA $404 per night from Nov 29 to Nov 30
CA $404
CA $452 total
Nov 29 - Nov 30
includes taxes & fees
Encore Boston Harbor
Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport

3 out of 5
230 Lee Burbank Hwy Revere MA
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Dec 4 to Dec 5
CA $139
CA $155 total
Dec 4 - Dec 5
includes taxes & fees
Hampton Inn Boston - Logan Airport
enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
1834 Revere Beach Pkwy Everett MA
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Nov 23 to Nov 24
CA $139
CA $155 total
Nov 23 - Nov 24
includes taxes & fees
enVision Hotel Boston Everett
See all 2,479 properties in Hamilton
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 Hamilton vacation package cost?
Starting from a low CA $706, a vacation package is your ticket to affordable travel. Custom build your Hamilton adventure by selecting from our wide range of hotels, flights and rental cars.
How do I get a cheap travel package to Hamilton?
You'll save big if you bundle your car rentals, flights and hotels into a Hamilton travel package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer over 550 partner airlines and 1,000,000 hotels throughout the world, so you'll always have plenty of options to choose from. Like to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Hamilton?
A getaway in Hamilton wouldn't be complete without checking out Appleton Farms Grass Rides. Why not stay within walking distance of this fantastic attraction?
How far in advance should I book my Hamilton vacation?
Be rewarded with the biggest variety at the lowest prices by booking your Hamilton vacation nice and early. Air carriers usually advertise flight tickets anywhere up to a year before departure, so secure your spot ASAP. Having said that, Expedia is committed to providing you with the best deals around, so it's always a good time to book your dream vacation!
What does an Expedia Hamilton travel package include?
Choose from any combination of rental cars, flights and hotels. Once you've made your booking, you can add some activities and experiences. Want to pick your airfare class? That's easy to do too. The choice is yours when it comes to arranging your dream Hamilton getaway.
What should I know before booking a Hamilton travel package?
You can save big by combining your flights, hotels and rental cars. Once you've created your package, you can add on things like activities or sightseeing tours. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with a Hamilton Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Hamilton vacation package?
You can. We understand that even the best-laid plans can fail, so we're happy to help if you need to make changes to your Hamilton vacation package. It may be possible to amend or cancel your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if your booking was made more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Stay near popular Hamilton attractions

Appleton Farms Grass Rides

Take the family on an outing to Appleton Farms Grass Rides during your trip to South Hamilton. While you're in the area, stroll along the beautiful beaches.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.