Wellington Vacations from $1,377

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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.

The Latest Wellington vacation packages

Price found within the past 48 hours. Click for updated prices.
Charles Hope Cape Town

Charles Hope Cape Town

4 out of 5
Cape Town City Centre
Price was $1,697, price is now $1,377 per person
$1,377
per person
Apr 21 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Cape Town (CPT)
10/10 Exceptional! (2 reviews)
From the great staff in the restaurant and front desk , to amazing housekeeping I was amazed by the great service ! The location is central to everything you could want in Cape Town. I found this to be a perfect stay for my needs !

Reviewed on Jan 26, 2026

Cape Cadogan Boutique Hotel

Cape Cadogan Boutique Hotel

5 out of 5
Cape Town City Centre
Price was $3,720, price is now $2,776 per person
$2,776
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cape Town (CPT)
9.6/10 Exceptional! (51 reviews)
Outstanding staff, continuously offering to be helpful. Good location, on a relatively quiet street just off of walkable Kloof Street but not in an area teeming with tourists. Afternoon tea and sweets. Restaurant in adjacent building with indoor and outdoor seating. No plans to return to Cape Town but would definitely stay here again.

Reviewed on Feb 6, 2026

One&Only Cape Town

One&Only Cape Town

5 out of 5
Victoria and Alfred Waterfront
Price was $5,239, price is now $4,154 per person
$4,154
per person
Apr 21 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Cape Town (CPT)
9.6/10 Exceptional! (366 reviews)
The most amazing hotel. Beyond amazing

Reviewed on Nov 26, 2025

Nova Constantia Boutique Residence

Nova Constantia Boutique Residence

5 out of 5
Constantia
Price was $2,069, price is now $1,700 per person
$1,700
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Cape Town (CPT)
9.6/10 Exceptional! (89 reviews)
Lee was a great help advising and booking restaurants and things to do

Reviewed on Feb 9, 2026

The Cellars-Hohenort

The Cellars-Hohenort

5 out of 5
Constantia
Price was $2,224, price is now $1,850 per person
$1,850
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Cape Town (CPT)
9.6/10 Exceptional! (154 reviews)
What a place! Everything is fabulous and the staff are exceptional. This was our 6th visit to the Cellars and it won’t be our last. The beautiful gardens together with the stylish interiors make for a luxurious and relaxing stay. The restaurant food is delicious too, what’s not to like?

Reviewed on Feb 6, 2026

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Discover the most popular places to visit in Wellington

Doolhof Wine Estate

You can enjoy a tasting or tour at Doolhof Wine Estate during your travels to Wellington. Discover the area's mountain views and wineries.

Doolhof Wine Estate

Welvanpas Family Vineyards

You can enjoy a tasting or tour at Welvanpas Family Vineyards during your travels to Wellington. Take in the theater scene and mountain views in the area.

Welvanpas Family Vineyards

Bosman Family Vineyards

You can enjoy a tasting or tour at Bosman Family Vineyards during your travels to Wellington. Take in the theater scene and mountain views in the area.

Bosman Family Vineyards

What to do in Wellington

Uncork the Cape : Stellenboch Half Day Wine Tour

Uncork the Cape : Stellenboch Half Day Wine Tour

$53
per adult
Uncork the Cape : Stellenboch Half Day Wine Tour
Beautiful views on the winelands day tour in Cape Town, South Africa

Cape Town Full Day Cape Winelands Tour

$120
per traveler
92% of travellers recommend
Cape Town Full Day Cape Winelands Tour
Aquila Afternoon Safari and Wine Tasting

Aquila Afternoon Safari and Wine Tasting

$156
per adult
Aquila Afternoon Safari and Wine Tasting
See all activities in Wellington

Wellington Hotel Deals

Val Du Charron Wine & Leisure Estate

Val Du Charron Wine & Leisure Estate

4 out of 5
Bovlei Road Wellington Western Cape
8.2/10 Very Good! (64 reviews)
No Security at night we r in South Africa. No staff on site between 9.30pm - 7am No telephones in the rooms No welfare checks No regular tv Poor breakfast Safe was NOT bolted to the wall u cud lift it up Absolute sham of a hotel

Reviewed on Feb 10, 2026

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Val Du Charron Wine & Leisure Estate
Oude Wellington

Oude Wellington

4 out of 5
Bainskloof (R301/3) Wellington Western Cape
7.8/10 Good! (34 reviews)
The manager was very nice, apart from that I wouldn't stay here again for the following: 1. We booked a "mountain view" family suite as advertised on Expedia, but the room had no mountain view and was not a family suite. I.e. false advertising. 2. We wanted to swim but the pool loungers were so dirty ...

Reviewed on Feb 11, 2026

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Oude Wellington
Boschendal Farm Estate

Boschendal Farm Estate

4.5 out of 5
Pniel Road Franschhoek Western Cape
$484 nightly
The price is $560 total per night from Feb 25 to Feb 26
$560 total
Feb 25 - Feb 26
Total with taxes and fees
9.4/10 Exceptional! (160 reviews)
Amazing farm estate, beautifully run and managed. Super staff. Great facilities within the estate. Our retreat cottage was lovely, comfortable, clean and great location. I would however say the kitchen needs to be better equipped- lack of utensils and glasses; also bedrooms very small. I feel the ...

Reviewed on Jan 4, 2026

Boschendal Farm Estate
See all 393 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.

Find the Best Wellington Vacation Packages

Wellington Essential Information

Language
Afrikaans
Currency
South African rands
Population
55,500
Max Temp Winter
65ºF
Max Temp Summer
80ºF
Top Sights
Bovlei, Diemersfontein Winery and Doolhof Wine Estate

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Frequently asked questions

How much does a Wellington vacation package cost?
Offering excellent value package deals from $1,377 on Expedia, you'll be surprised at how little a vacation to Wellington costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Wellington?
If you'd like to book a cheap Wellington vacation package, consider visiting in July, November and December. You'll generally find lower prices on hotels and airfares during these months — ideal for travelers wishing to save money.
How many days is enough for Wellington?
With a well-planned itinerary, you can easily visit the main Wellington sights in a handful of days. But if you prefer to explore off the beaten track or go on day trips, think about booking your Wellington vacation for longer.
How to find the best Wellington package deals?
Begin your search for a Wellington package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Wellington package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Wellington adventure underway.
Is it cheaper to book a Wellington vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and stays individually. Better still, you can personalize your Wellington getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Wellington?
If you're planning an impromptu Wellington trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Wellington?

  1. Pick your travel dates: The things you'd like to do in Wellington and your preferred season will help you decide when to go.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to save for your trip to Wellington. Then, choose a hotel that works with your budget, whether that's an affordable option or a deluxe getaway.
  3. Discover Wellington with our trip planning tool: Gain insights into the most popular attractions and best hotels for your trip to Wellington. You can also save your favorite places, collaborate with friends and family and manage all your plans in one place.
  4. Determine how many days away: Start by making a list of all the attractions you want to experience in Wellington. Then, estimate how long you'll need for each, as well as any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Wellington vacation package.
  6. Add on excursions and experiences: Have a look at our travel guide to find some incredible things to do in Wellington in Wellington. Book tickets or make reservations before you go to save time and avoid the hassle of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Wellington vacation packages?
Your Wellington trip should be a relaxing escape from your daily routine, not a reason for money worries. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.