Whitby 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
Price found within the past 48 hours. Click for updated prices.
  • Terrace/patio
    Aug 3 - Aug 15

    Two Peas In A Pod + Flight

    Khandallah
    10 nights
    3.5 star property
    9.4/10 - Exceptional (3 reviews)
    "Place was lovely and compact. Had everything you needed for a few days. Host was lovely too"
    Reviewed March 16, 2025
    Roundtrip • Winnipeg (YWG) - Wellington (WLG)
    YWG - WLG • 2 stops WLG - YWG • 2 stops
    CA $3,336
    CA $2,962
    per traveller
    found 12 hours ago
    Two Peas In A Pod
  • Signature Apartment | Living area
    Aug 3 - Aug 15

    U Suites on Cuba + Flight

    Te Aro
    10 nights
    3.5 star property
    7.0/10 - Good (2 reviews)
    "Nice and close to the cbd. Had a good stay."
    Reviewed February 14, 2025
    Roundtrip • Winnipeg (YWG) - Wellington (WLG)
    YWG - WLG • 2 stops WLG - YWG • 2 stops
    CA $4,171
    CA $3,591
    per traveller
    found 12 hours ago
    U Suites on Cuba
  • Exterior
    Aug 3 - Aug 15

    Rydges Wellington Airport + Flight

    Rongotai
    10 nights
    4.5 star property
    9.2/10 - Wonderful (1,002 reviews)
    "Great location and easy to get to the check in area but make sure you pay attention to which buttons you press in the lift when trying to Exit the hotel as one side takes you to the road level, the other side takes you to the basement and once you get out you can't get back in the lift so you have to walk up 3 flights to main reception again."
    Reviewed May 29, 2026
    Roundtrip • Winnipeg (YWG) - Wellington (WLG)
    YWG - WLG • 2 stops WLG - YWG • 2 stops
    CA $3,501
    CA $3,062
    per traveller
    found 12 hours ago
    Rydges Wellington Airport
  • Exterior
    Aug 3 - Aug 15

    Sofitel Wellington + Flight

    Wellington CBD
    10 nights
    5.0 star property
    9.4/10 - Exceptional (757 reviews)
    "Very welcoming staff, easy check in, great location. "
    Reviewed May 10, 2026
    Roundtrip • Winnipeg (YWG) - Wellington (WLG)
    YWG - WLG • 2 stops WLG - YWG • 2 stops
    CA $3,707
    CA $3,245
    per traveller
    found 12 hours ago
    Sofitel Wellington
  • Deluxe Room, 1 King Bed, Harbour View
    Aug 3 - Aug 15

    Rydges Wellington + Flight

    Pipitea
    10 nights
    4.5 star property
    8.4/10 - Very good (1,000 reviews)
    "Very handy location, staff very friendly, great breakfast, spacious room and very comfortable bed"
    Reviewed May 23, 2026
    Roundtrip • Winnipeg (YWG) - Wellington (WLG)
    YWG - WLG • 2 stops WLG - YWG • 2 stops
    CA $3,505
    CA $3,073
    per traveller
    found 12 hours ago
    Rydges Wellington

Where to stay in Whitby

Find the best Whitby areas and neighborhoods for the activities you enjoy most. Learn more about Whitby
Plimmerton

Plimmerton

2 out of top 10 points of interest in this area

Unique features of Plimmerton include the beaches and bars. Make a stop by Plimmerton Beach or South Beach while you're exploring the area.

Find hotels in Plimmerton

Whitby Hotel Deals

James Cook Hotel Grand Chancellor

James Cook Hotel Grand Chancellor

4.5 out of 5
147 The Terrace Wellington
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Jun 21 to Jun 22
CA $95
CA $110 total
Jun 21 - Jun 22
includes taxes & fees
8.8/10 Excellent! (1,743 reviews)
"Rooms were fine but very noisy. I could hear the person next doors tv perfectly which was not appreciated late at night"

Reviewed on May 29, 2026

James Cook Hotel Grand Chancellor
Rydges Wellington Airport

Rydges Wellington Airport

4.5 out of 5
28 Stewart Duff Drive, Rongotai Wellington
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Jun 2 to Jun 3
CA $135
CA $155 total
Jun 2 - Jun 3
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Great location and easy to get to the check in area but make sure you pay attention to which buttons you press in the lift when trying to Exit the hotel as one side takes you to the road level, the other side takes you to the basement and once you get out you can't get back in the lift so you have ..."

Reviewed on May 29, 2026

Rydges Wellington Airport
Rydges Wellington

Rydges Wellington

4.5 out of 5
75 Featherston St Wellington
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from May 31 to Jun 1
CA $126
CA $145 total
May 31 - Jun 1
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Very handy location, staff very friendly, great breakfast, spacious room and very comfortable bed"

Reviewed on May 23, 2026

Rydges Wellington
See all 668 properties in Whitby
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 Whitby vacation package cost?
From as little as , you can tailor your Whitby vacation package. Simply combine flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Whitby?
Imagine all the awesome things you could do in Whitby with a pile of extra cash in your pocket. Watch your savings stack up when you combine your flights, hotels and other bookings into a Whitby vacation package. You have plenty of choice with Expedia too. In fact, you can select from over 550 airlines and 1,000,000 hotels throughout the world. Whether you're heading off with the whole family or adventuring alone, planning a trip to Whitby is better with a package.
What are the top hotels in Whitby?
Sleeps Up To 16 Guests is one of Whitby's most sought-after properties. Book a room here and you'll be able to slumber peacefully knowing you're in good hands.
How far in advance should I book my Whitby vacation?
It's tricky picking the ideal time for airfares, but we generally suggest the earlier, the better. Many international journeys on Expedia become available up to a year in advance. If you can't book ahead, don't despair. Cheap prices appear from time to time just weeks before departure dates.
What does an Expedia Whitby travel package include?
Flights, hotels and a reliable car for all your fun road trip adventures. Simply pick and choose your favorite bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to crafting your Whitby trip, you're the boss!
What should I know before booking a Whitby travel package?
Locking in all the parts of your trip together is a simple way to save. Bundle your airfares, rental cars and hotels into a handy package. But hotels aren't your only option. Expedia features all sorts of properties, including vacation rentals such as beachside villas and city residences. You've got loads of choices!
Can I choose my airline with a Whitby Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You get to decide. We have more than 550 airline partners around the world, so you have loads of choice when creating your Whitby getaway.
If I'm not able to travel, can I cancel my Whitby vacation package?
Yes, it's possible to cancel your Whitby booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change for free if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Things to do

Half Day Lord of the Rings Tour

Half Day Lord of the Rings Tour

CA $155
per adult
94% of travellers recommend
Half Day Lord of the Rings Tour
Seal Coast Safari - Exclusive access to Wellington's secret coast

Seal Coast Safari - Exclusive access to Wellington's secret coast

CA $159
per adult
100% of travellers recommend
Seal Coast Safari - Exclusive access to Wellington's secret coast
Wellington: Return Cable Car Ticket

Wellington: Return Cable Car Ticket

CA $10
per adult
78% of travellers recommend
Wellington: Return Cable Car Ticket
See all activities in Porirua

Explore a world of travel with Expedia

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