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.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was CA $1,455, price is now CA $968 per person
CA $968
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
The area is very good for walking and getting the sense of Boston. The rooms are clean and most importantly the staff is excellent.

Reviewed on May 8, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $2,769, price is now CA $1,773 per person
CA $1,773
per person
Jun 15 - Jun 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!

Reviewed on Sep 20, 2025

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
Price was CA $5,169, price is now CA $3,563 per person
CA $3,563
per person
Jun 16 - Jun 21
found 17 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (453 reviews)
Top notch. Every member of the staff was a credit to his or her profession.

Reviewed on May 3, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,056, price is now CA $1,425 per person
CA $1,425
per person
Jun 22 - Jun 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (254 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $6,232, price is now CA $4,321 per person
CA $4,321
per person
Jul 25 - Aug 1
found 22 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.4/10 Exceptional! (687 reviews)
Very peaceful except the folks upstairs. We were bottom level ocean view. Lovely newly renovated room. Incredible staff. I live 11 hrs away and parents both in nearby wonderful nursing home, LC. Easy drive to see them. Family home gone now but was certainly made to feel at home here.

Reviewed on May 6, 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 $429 per night from May 22 to May 23
CA $429
CA $480 total
May 22 - May 23
includes taxes & fees
9.6/10 Exceptional! (3,756 reviews)
Clean room staff breakfast casino

Reviewed on May 8, 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 $354 per night from May 10 to May 11
CA $354
CA $412 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (3,769 reviews)
Very practical hotel with a tunnel to the airport. The room was OK.

Reviewed on May 8, 2026

Hilton Boston Logan Airport
La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville

3 out of 5
23 Cummings St Somerville MA
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from May 10 to May 11
CA $185
CA $206 total
May 10 - May 11
includes taxes & fees
7.6/10 Good! (3,329 reviews)
No Comment

Reviewed on May 8, 2026

La Quinta Inn & Suites by Wyndham Boston Somerville
See all 2,451 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
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Frequently asked questions

How much does a Hamilton vacation package cost?
Starting from a low CA $968, 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.