Wellington Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Wellington Vacation

Entertainment, history, art and more … There's so much to experience with a Wellington vacation package. And with the ability to customize your city getaway, you know it'll be one that's tough to forget. If a sightseeing tour is on the to-do list during your trip to Wellington, check out popular attractions like Doolhof Wine Estate, Diemersfontein Winery and Bosman Family Vineyards. Whatever your travel plans or budget, putting together a tailored Wellington vacation is a cinch with Expedia.

Top Wellington Vacation Deals

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

Bliss Boutique Hotel

5 out of 5
Sunset Beach
Price was CA $3,369, price is now CA $2,770 per person
CA $2,770
per person
Dec 15 - Dec 19
just found
Roundtrip flight included
Toronto (YYZ) to Cape Town (CPT)
9.4/10 Exceptional! (97 reviews)
The staff were fantastic. The breakfast was delicious.

Reviewed on Oct 15, 2026

The Cellars-Hohenort

The Cellars-Hohenort

5 out of 5
Constantia
Price was CA $5,249, price is now CA $4,319 per person
CA $4,319
per person
Dec 15 - Dec 19
just found
Roundtrip flight included
Toronto (YYZ) to Cape Town (CPT)
9.6/10 Exceptional! (172 reviews)
The setting is absolutely beautiful, the gardens are well maintained.

Reviewed on Nov 3, 2026

The Tree House Boutique Hotel

The Tree House Boutique Hotel

5 out of 5
Cape Town City Centre
Price was CA $3,710, price is now CA $3,096 per person
CA $3,096
per person
Dec 15 - Dec 19
just found
Roundtrip flight included
Toronto (YYZ) to Cape Town (CPT)
9.6/10 Exceptional! (243 reviews)
Lovely stay, great hotel and fantastic location

Reviewed on Oct 23, 2026

Zest Boutique Hotel

Zest Boutique Hotel

5 out of 5
Cape Town City Centre
Price was CA $3,341, price is now CA $2,796 per person
CA $2,796
per person
Dec 15 - Dec 19
just found
Roundtrip flight included
Toronto (YYZ) to Cape Town (CPT)
9.8/10 Exceptional! (214 reviews)
Wonderful staff

Reviewed on Jul 9, 2026

Cape Cadogan Boutique Hotel

Cape Cadogan Boutique Hotel

5 out of 5
Cape Town City Centre
Price was CA $3,834, price is now CA $3,214 per person
CA $3,214
per person
Dec 15 - Dec 19
just found
Roundtrip flight included
Toronto (YYZ) to Cape Town (CPT)
9.6/10 Exceptional! (55 reviews)
Nice place

Reviewed on Aug 13, 2026

Ready to book your vacation to Wellington?

 

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Wellington Hotel Deals

Val Du Charron Wine & Leisure Estate

Val Du Charron Wine & Leisure Estate

4 out of 5
Bovlei Road Wellington Western Cape
The price is CA $210 per night from Nov 6 to Nov 7
CA $210
CA $242 total
Nov 6 - Nov 7
includes taxes & fees
8.4/10 Very good! (68 reviews)
"Nice clean room. Comfortable bedding. Clean and bright building. Delicious breakfast and amazing views and location. Staff were incredibly helpful and friendly. WIshed we could have stayed longer"

Reviewed on Aug 6, 2026

Val Du Charron Wine & Leisure Estate
Ross Farms Self-Catering Cottages.

Ross Farms Self-Catering Cottages.

Wellington WC
Get rates
Ross Farms Self-Catering Cottages.
Babylonstoren

Babylonstoren

5 out of 5
Babylonstoren Road Franschhoek Western Cape
Get rates
Babylonstoren
See all 440 properties in Wellington
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
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Wellington attractions

Bain's Whisky Distillery

You can take time to visit Bain's Whisky Distillery during your travels to Wellington. Take in the theater scene and mountain views in the area.
See properties

What to do in Wellington

Uncork the Cape : Stellenboch Half Day Wine Tour

Uncork the Cape : Stellenboch Half Day Wine Tour

CA $77
per adult
Uncork the Cape : Stellenboch Half Day Wine Tour
From CapeTown: Stellenbosch Half Day Wine Tour

From CapeTown: Stellenbosch Half Day Wine Tour

CA $80
per adult
98% of travellers recommend
From CapeTown: Stellenbosch Half Day Wine Tour
Beautiful views on the winelands day tour in Cape Town, South Africa

Cape Town Full Day Cape Winelands Tour

CA $166
per traveller
92% of travellers recommend
Cape Town Full Day Cape Winelands Tour
See all activities in Wellington

Frequently asked questions

How much does a Wellington vacation package cost?
You can snap up a vacation package to this popular destination from CA $2,770 on Expedia. But how much your vacation to Wellington costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Wellington?
Travel in the off-peak season and you're likely to find cheap Wellington vacation packages. Remember that public holidays and local events and festivals can impact prices, so do your research before booking.
How many days is enough for Wellington?
Typically, a handful of days is enough to visit the top attractions during your Wellington vacation. But if you'd like to have more time to unwind or go on day tours, consider extending your trip.
How to find the best Wellington package deals?
Begin your search for a Wellington package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Wellington package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Wellington escape off to a flying start.
Is it cheaper to book a Wellington vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Wellington vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Wellington?
If you've got your Wellington travel dates finalized, book as early as you can to score some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Wellington?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Wellington.
  2. Budget wisely: On top of the cost of your accommodations, you'll need to factor in other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that could crop up during your trip to Wellington.
  3. Decide how long to go away for: Now that you're up to speed on Wellington, you can work out the ideal length of your break. Pull together a rough itinerary and give yourself enough time to cover everything you want to do.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Wellington vacation package that brings all your bookings together.

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