A coastal landscape with a cliff, a sandy beach, and a calm sea.

Photo by Rebecca Figueroa

Cliffside Vacations from $516

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  • Your Cliffside Vacation

    Book a Cliffside vacation package and discover the way of life and rhythm of this sought-after neighborhood. With all your travel plans taken care of, the only thing you need to worry about here is having a great time. Want to explore the sights during your trip to Cliffside? Be sure to stop by nearby attractions like Scarborough Crescent Park, RC Harris Filtration Plant and Dentonia Park Golf Course. Expedia can help you turn your dream Cliffside vacation into reality, no matter your travel plans or budget.

    The Latest Cliffside Vacation Packages

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    Where to stay in Cliffside

    Find the best Cliffside areas and neighborhoods for the activities you enjoy most.

    A city skyline with modern skyscrapers, a prominent tower, and a calm river with boats.

    A bustling urban square with a large billboard advertising 'Moonshine' and a fountain in the center.

    The Toronto skyline with the 'TORONTO' sign in the foreground and a bridge in the background.

    A frozen ice skating rink in front of a historic building with a clock tower.

    A red bus with 'Public' and 'Mobile' advertising on the side, driving on a city street with buildings and a tower in the background.

    View properties in map for Downtown Toronto

    Downtown Toronto

    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.

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    A modern building with a unique angular design, illuminated at dusk.

    Photo by Leo Li

    The Ontario Science Centre with a large stone sculpture in the foreground.

    A cityscape with autumn foliage, residential areas, and high-rise buildings.

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

    A garden with a stone pathway, red flowers, and a fountain.

    View properties in map for North York

    North York

    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.

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    A nighttime city street with a moving train, illuminated buildings, and a sign for the Princess of Wales Theatre.

    A brightly lit street with a tram, modern buildings, and a restaurant named LUMA.

    A cityscape with modern buildings, a glass structure, and a METROCENTRE.

    A cityscape at night with illuminated buildings, a distinctive tower, and a modern spherical structure.

    A modern cityscape with a prominent tower and surrounding high-rise buildings.

    View properties in map for Toronto Entertainment District

    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!

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    A city skyline with modern skyscrapers, a marina with boats, and a large body of water.

    A waterfront cityscape with modern skyscrapers, a marina, and a park area.

    A calm river with sailboats, a rocky shoreline, and lush greenery.

    A river with a pedestrian bridge, grassy banks, and modern buildings in the background.

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

    View properties in map for Etobicoke

    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.

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    A riverbank with a rocky cliff and trees.

    The entrance to the Toronto Zoo with a sign, green gates, and visitors.

    A sign welcoming visitors to Toronto Zoo with a crowd of people in front.

    A calm river with white cliffs and a clear blue sky.

    Photo by Skyy

    A coastal landscape with a rocky cliff, a sandy foreground, and a calm bay with clear blue water.

    Photo by Valerie Guiser

    View properties in map for Scarborough

    Scarborough

    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.

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    Cliffside Hotel Deals

    Toronto Don Valley Hotel and Suites

    A hotel lobby with a reception desk, seating area, and a view of the pool.
    • Address: 175 Wynford Drive, Toronto, ON, M3C1J3, CA
    • Location: 4.4 mi from Cliffside
    • Star rating: 3.5/5
    • Guest rating: 7.8/10 (Good, 7299 reviews)
    • Price: $96 nightly, $115 total, Dec 15 - Dec 16, Total with taxes and fees
    • Review: Breakfast is not worth it. Kids bowl of cereal (the small boxes you get at Dollarstore)$9!!! Small drink of juice was extra as well!! Cost me over $60 my 2 kids and myself to have breakfast! Next time we will go somewhere else for a better, more option (kids friendly) breakfast. We didnt spend alot of time there as we were just down for a day at the Royal Winter Fair.

    Best Western Plus Executive Inn

    An indoor swimming pool with a high ceiling, large windows, and a tiled floor.
    • Address: 38 Estate Drive, Toronto, ON, M1H2Z1, CA
    • Location: 5.2 mi from Cliffside
    • Star rating: 3/5
    • Guest rating: 8.6/10 (Excellent, 1459 reviews)
    • Price: $118 nightly, $142 total, Nov 15 - Nov 16, Total with taxes and fees
    • Review: Perfect location. Great propert

    One King West Hotel & Residence

    A modern living room with a fireplace, comfortable seating, and a large TV.
    • Address: 1 King Street West, Toronto, ON, M5H1A1, CA
    • Location: Financial District, 7.9 mi from Cliffside
    • Star rating: 4/5
    • Guest rating: 9.4/10 (Exceptional, 8875 reviews)
    • Price: $158 nightly, $189 total, Dec 11 - Dec 12, Total with taxes and fees
    • Review: Nice clean hotel, friendly staff and super quick elevators

    Crowne Plaza Toronto North York by IHG

    Lobby
    • Address: 900 York Mills Rd, Toronto, ON, M3B3H2, CA
    • Location: North York, 6.3 mi from Cliffside
    • Star rating: 4/5
    • Guest rating: 8.4/10 (Very good, 3833 reviews)
    • Price: $106 nightly, $127 total, Dec 13 - Dec 14, Total with taxes and fees

    Fairmont Royal York

    A cityscape with a mix of modern and historic buildings, including a prominent Art Deco structure.
    • Address: 100 Front St West, Toronto, ON, M5J1E3, CA
    • Location: Financial District, 8.1 mi from Cliffside
    • Star rating: 5/5
    • Guest rating: 9/10 (Wonderful, 8655 reviews)
    • Price: $220 nightly, $263 total, Nov 22 - Nov 23, Total with taxes and fees
    • Review: Staff were incredibly helpful and attentive.

    Holiday Inn Toronto Downtown Centre by IHG

    A modern hotel lobby with an escalator, glass partitions, a colorful abstract painting, and yellow seating.
    • Address: 30 Carlton Street, Toronto, ON, M5B2E9, CA
    • Location: 7.6 mi from Cliffside
    • Star rating: 3.5/5
    • Guest rating: 8.6/10 (Excellent, 6825 reviews)
    • Price: $129 nightly, $154 total, Dec 12 - Dec 13, Total with taxes and fees

    Hilton Toronto

    A spacious lounge area with a bar, comfortable seating, and a decorative ceiling light fixture.
    • Address: 145 Richmond St W, Toronto, ON, M5H2L2, CA
    • Location: Financial District, 8.2 mi from Cliffside
    • Star rating: 4/5
    • Guest rating: 9/10 (Wonderful, 2413 reviews)
    • Price: $155 nightly, $185 total, Dec 11 - Dec 12, Total with taxes and fees

    The Omni King Edward Hotel

    A hotel entrance with a checkered pavement, a large awning, and a stone planter with plants.
    • Address: 37 King St E, Toronto, ON, M5C1E9, CA
    • Location: St. Lawrence, 7.8 mi from Cliffside
    • Star rating: 4.5/5
    • Guest rating: 9.6/10 (Exceptional, 2879 reviews)
    • Price: $178 nightly, $213 total, Nov 15 - Nov 16, Total with taxes and fees

    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.

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    * Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.