Hamilton Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $2,462, price is now CA $1,541 per person
CA $1,541
per person
Jun 1 - Jun 8
found 13 hours ago
Roundtrip flight included
Hamilton (YHM) to Boston (BOS)
8.6/10 Excellent! (1,395 reviews)
Our room was always hot and our sheets had stains and the shower was stained pink

Reviewed on Mar 29, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $4,273, price is now CA $2,516 per person
CA $2,516
per person
Jun 21 - Jun 24
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
clean room. friendly and helpful staff. good breakfast in reasonable price. hope they have a boutique store to sell Langham signature products, especially the home fragrance products.

Reviewed on Mar 29, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,468, price is now CA $1,570 per person
CA $1,570
per person
Jun 13 - Jun 17
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $7,655, price is now CA $4,917 per person
CA $4,917
per person
Jun 1 - Jun 8
found 13 hours ago
Roundtrip flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.

Reviewed on Mar 23, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $7,578, price is now CA $4,931 per person
CA $4,931
per person
Jun 1 - Jun 8
found 13 hours ago
Roundtrip flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (238 reviews)
The photos doesn’t give this place justice.

Reviewed on Mar 24, 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 $346 per night from Apr 29 to Apr 30
CA $346
CA $387 total
Apr 29 - Apr 30
includes taxes & fees
9.6/10 Exceptional! (3,624 reviews)
Not applicable

Reviewed on Mar 30, 2026

Encore Boston Harbor
Hilton Boston Logan Airport

Hilton Boston Logan Airport

4 out of 5
One Hotel Drive Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $459 per night from Apr 5 to Apr 6
CA $459
CA $534 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (3,705 reviews)
Nice hotel

Reviewed on Mar 29, 2026

Hilton Boston Logan Airport
Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea

2.5 out of 5
200 2nd Street Chelsea MA
Fully refundableReserve now, pay when you stay
The price is CA $234 per night from Apr 6 to Apr 7
CA $234
CA $261 total
Apr 6 - Apr 7
includes taxes & fees
9/10 Wonderful! (2,827 reviews)
Clean room, good breakfast and nice service 👌

Reviewed on Mar 29, 2026

Hampton Inn Boston Logan Airport Chelsea
See all 2,383 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
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Family Vacations
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Frequently asked questions

How much does a Hamilton vacation package cost?
Starting from a low CA $1,541, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.