Little Italy Vacation Packages 2026 from $580

Your Little Italy Vacation

Book a customized vacation package to Little Italy and immerse yourself in its nightlife, distilleries and craft breweries and cafes. However you plan to spend your time in this food-lovers neighborhood, you'll find loads of opportunities for fun and relaxation. Can't wait to head out and see the sights during your trip to Little Italy? Be sure to check out nearby attractions such as CN Tower, Rogers Centre and Scotiabank Arena. Whatever your travel goals or budget, booking your perfect Little Italy vacation is a cinch with Expedia.

The Latest Little Italy Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Modern Apartments in North York

North York

$580

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

8.2/10 Very Good! (373 reviews)

This unit is well located in the city. Secured underground parking and easy access to Sheppard-Younge station at the building. Lots of amenities near by. The unit was clean and decently appointed typical for vacay rentals. It is a little tired. Little things like broken toilette paper dispenser, no hooks in bathroom furnishings that have been well used. It was a great option for our stay in Toronto.

Reviewed on Sep 3, 2026

1 Hotel Toronto

Downtown Toronto

$1,527

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (792 reviews)

Hotel Riu Plaza Toronto

Downtown Toronto

$909

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.4/10 Exceptional! (4,590 reviews)

Altitude Suites Bay Street by Teristo Group

Downtown Toronto

$922

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

8.6/10 Excellent! (9 reviews)

Modern Downtown Apartments

Downtown Toronto

$711

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

8.2/10 Very Good! (608 reviews)

Check-in went great. The space was clean. We love the location. There were three of us and we only had towels for one person. I notified the Booking They responded a bit later that they would look into this and have someone bring some up for us. Unfortunately, we checked out before hearing anything back or receiving any additional towels. Upon checkout, I let the Booking know again that we didn't receive any towels. And they brought to they were in the dryer. I wish I had known that earlier. Two of us slept in the bed, which was a very hard mattress and one slept on the couch. The individual on the couch had a much better sleep.

Reviewed on Aug 31, 2026

Where to stay in Little Italy

Find the best Little Italy areas and neighborhoods for the activities you enjoy most. Learn more about Little Italy

A row of international flags in front of a historic building with ornate architecture.

Downtown Toronto

6 out of top 10 points of interest in this area

Dive into the bustling Entertainment District with its lively restaurants, nightclubs, and live theatre, or explore the upscale Yorkville area, boasting designer boutiques and world-class galleries. Don't miss the iconic Royal Ontario Museum and the revitalized Harbourfront area.

A well-manicured garden with geometric hedges, a variety of flowering plants, and a central tall tree.

North York

1 out of top 10 points of interest in this area

Home to interactive museums like Ontario Science Centre and Aga Khan Museum, North York offers ample shopping at Yorkdale Shopping Centre and Fairview Mall. Easily accessible via TTC subway and bus lines.

A row of Victorian-style houses with steep gabled roofs, surrounded by lush greenery and a well-maintained lawn.

Etobicoke

Suburban and industrialized, Etobicoke boasts numerous parks like James Gardens and Centennial Park, as well as golf courses such as St. George's Golf and Country Club. Enjoy convenient public transportation via TTC and GO stations.

A large wooden climbing structure with multiple levels and ropes.

Scarborough

1 out of top 10 points of interest in this area

Situated atop Scarborough Bluffs, this diverse district offers shopping at Scarborough Town Centre and animal encounters at Toronto Zoo. Explore natural landmarks like Rouge Park and the Scarborough Bluffs, or hop on the TTC for easy transit access.

An aerial view of a city with a river, high-rise buildings, and a bridge.

Toronto Entertainment District

Downtown Toronto's vibrant hub features theatres, performing arts centres, and Toronto Blue Jays games, with numerous bars and restaurants catering to diverse crowds. Don't miss the iconic CN Tower!

Little Italy Hotel Deals

Chelsea Hotel, Toronto

33 Gerrard St W Toronto ON

$160 nightly

$191 total

Sep 7 - Sep 8

Total with taxes and fees

9/10 Wonderful! (1,673 reviews)

"Rooms are at smaller end and check-in queue is long. But overall value for money, clean, good housekeeping."

Reviewed on Sep 4, 2026

Toronto Don Valley Hotel and Suites

175 Wynford Drive Toronto ON

$99 nightly

$119 total

Oct 4 - Oct 5

Total with taxes and fees

7.8/10 Good! (6,942 reviews)

"Great pools love balcony and friendly staff !"

Reviewed on Sep 4, 2026

Holiday Inn Toronto Downtown Centre by IHG

30 Carlton Street Toronto ON

$206 nightly

$247 total

Sep 6 - Sep 7

Total with taxes and fees

See all 6,392 properties in Little Italy

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.