Guildwood Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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
Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Jun 30 - Jul 16

    Oak House Residence + Flight

    Downtown Toronto
    16 nights
    3.0 star property
    9.0/10 - Wonderful (19 reviews)
    Return • Auckland (AKL) - Toronto (YYZ)
    AKL - YYZ • 2 stops YYZ - AKL • 2 stops
    NZ$7,080
    NZ$6,286
    per traveller
    found 1 day ago
    Oak House Residence
  • Luxury Suite, 2 Double Beds
    Jun 30 - Jul 16

    Town Inn Suites Hotel + Flight

    Downtown Toronto
    16 nights
    3.5 star property
    8.6/10 - Excellent (3,768 reviews)
    "OK"
    Reviewed May 29, 2026
    Return • Auckland (AKL) - Toronto (YYZ)
    AKL - YYZ • 2 stops YYZ - AKL • 2 stops
    NZ$9,586
    NZ$7,854
    per traveller
    found 1 day ago
    Town Inn Suites Hotel
  • Signature Suite, 2 Bedrooms, 2 Bathrooms
    Jun 30 - Jul 16

    The York Suites + Flight

    Downtown Toronto
    16 nights
    3.5 star property
    10/10 - Exceptional (1 review)
    "I found the check in process terrible. Nobody answered my phone call. Hotel.com did not give an accurate address so I had a hard time getting there. After a long day at the airport with 7hr delay in my flight and the time of my arrival, I was pissed. . After check in, I found the place great. Now I m hooked and will come back. Go figure"
    Reviewed May 27, 2026
    Return • Auckland (AKL) - Toronto (YYZ)
    AKL - YYZ • 2 stops YYZ - AKL • 2 stops
    NZ$7,873
    NZ$6,557
    per traveller
    found 1 day ago
    The York Suites

Our guide on where to stay in Guildwood

Find the best Guildwood areas and neighborhoods for the activities you enjoy most. Learn more about Guildwood
Downtown Toronto

Downtown Toronto

5 out of top 10 points of interest in this area
4.5/5(124 area reviews)

Find fabulous museums and galleries among the immense architecture in this town center, a global leader in design and innovation.

Find hotels in Downtown Toronto

Our pick of the best Guildwood Hotel Deals

Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
33 Gerrard St W Toronto ON
Fully refundableReserve now, pay when you stay
The price is NZ$310 per night from 31 May to 1 June
NZ$310
31 May - 1 June
includes taxes & fees
8.4/10 Very Good! (14,996 reviews)
"Beautiful, clean and safe hotel! We just loved the hotel! The only downfall was that the reception staff wasn't as friendly because they were overwhelmed by the traffic it was receiving. Yet, I have to say that the cleaning crew were just so professional and courteous! They should be at the front ..."

Reviewed on 29 May 2026

Chelsea Hotel, Toronto
DoubleTree by Hilton Hotel Toronto Downtown

DoubleTree by Hilton Hotel Toronto Downtown

4 out of 5
108 Chestnut St Toronto ON
Fully refundableReserve now, pay when you stay
The price is NZ$430 per night from 31 May to 1 June
NZ$430
31 May - 1 June
includes taxes & fees
9/10 Wonderful! (6,046 reviews)
"Great location. Staff were friendly. Pool was nice. Very good value."

Reviewed on 29 May 2026

DoubleTree by Hilton Hotel Toronto Downtown
One King West Hotel & Residence

One King West Hotel & Residence

4 out of 5
1 King Street West Toronto ON
The price is NZ$491 per night from 7 June to 8 June
NZ$491
7 June - 8 June
includes taxes & fees
9.4/10 Exceptional! (7,850 reviews)
"Easy to drive in, easy parking, easy subway access and easy drive out"

Reviewed on 30 May 2026

One King West Hotel & Residence
See all 4,991 properties in Guildwood
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.

Frequently asked questions

How much does a Guildwood holiday package cost?
We make it simple to travel the world, with Guildwood holiday packages starting from as little as . You'll have the flexibility to bundle your preferred hotels, airlines and car rental. For the ultimate escape, why not add some experiences and tours to your itinerary?
How do I get a cheap travel package to Guildwood?
If you love scoring a bargain, combine your bookings into a Guildwood holiday package. Whether you're looking for flights, hotels, rental cars or day tours, you can book them all in one place. You'll have plenty of choice at your fingertips too. Expedia has more than 550 airlines and 1 000 000 hotel options all over the world to select from. Fly with who you want, stay in a place you like and save a bundle — now that's the perfect escape!
Where should I stay in Guildwood?
Take the hassle out of sightseeing by staying in a hotel within walking distance of Guildwood's terrific attractions. Canadas Wonderland and CN Tower are two of the best in the area.
How far in advance should I book my Guildwood holiday?
Reward yourself with the widest variety at the cheapest prices by booking your holiday to Guildwood nice and early. Airlines generally publish flights anywhere up to a year prior to departure, so secure your spot as soon as possible. That being said, Expedia is dedicated to giving you the best deals around, so there's never a bad time to book your dream holiday!
What does an Expedia Guildwood travel package include?
Select from any combination of hotels, rental cars and flights. Once you've made your booking, you can add tours and activities. Want to pick your fare class? That's also easy to do. The choice is yours when it comes to arranging your dream Guildwood getaway.
What should I know before booking a Guildwood travel package?
Find deals to suit your budget with an Expedia package. Airfares, hotels, rental cars — we've got them all. You'll save big bucks just by bundling your bookings. Whether you're going on a winter snow adventure or getting some sun on a warm beach, your perfect getaway is only clicks away.
Can I choose my airline with a Guildwood Expedia holiday package?
Yes, you sure can. We have more than 550 partner airlines around the world, so fly with the carrier that best suits your budget needs.
If I'm not able to travel, can I cancel my Guildwood holiday package?
Yes, you can. We realise things don't always go to plan, so we're happy to help if you have to make changes to your Guildwood holiday package. You may be able to cancel or change your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked 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.

Discover the most popular places to visit in Guildwood

Rogers Centre

Rogers Centre

4.5/5(10 reviews)

Come to this multipurpose stadium to watch baseball matches and football games, listen to concerts of famous bands, see family shows or simply tour this central entertainment complex.

Rogers Centre
Canada's Wonderland

Canada's Wonderland

4/5(2 reviews)

Get your adrenaline pumping at this fun-filled amusement park where the thrills come fast and furious.

Canada's Wonderland
CN Tower

CN Tower

4/5(26 reviews)

This iconic Toronto landmark offers breathtaking views over the whole city and, on a clear day, as far as Niagara Falls.

CN Tower

Activities

Toronto Hop-On Hop-Off Bus Tour & Free Harbour Cruise

City Sightseeing Toronto Hop-On Hop-Off Bus Tour

NZ$85
per adult
84% of travellers recommend
City Sightseeing Toronto Hop-On Hop-Off Bus Tour
Toronto: Casa Loma Entry Ticket

Toronto: Casa Loma Entry Ticket

NZ$55
per adult
90% of travellers recommend
Toronto: Casa Loma Entry Ticket
Niagara Falls Day Tour from Toronto

Niagara Falls Day Tour from Toronto

NZ$121
per adult
96% of travellers recommend
Niagara Falls Day Tour from Toronto
See all activities in Toronto
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.