Wellington Vacations from $2,792

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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.
Terra by O'Two Hotels

Terra by O'Two Hotels

4 out of 5
Mouille Point
Price was $3,499, price is now $2,792 per person
$2,792
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Cape Town (CPT)
9.2/10 Wonderful! (78 reviews)

Cape Grace, A Fairmont Managed Hotel

Cape Grace, A Fairmont Managed Hotel

5 out of 5
Victoria and Alfred Waterfront
Price was $5,914, price is now $4,538 per person
$4,538
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Cape Town (CPT)
9.6/10 Exceptional! (157 reviews)

One&Only Cape Town

One&Only Cape Town

5 out of 5
Victoria and Alfred Waterfront
Price was $6,744, price is now $5,256 per person
$5,256
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Cape Town (CPT)
9.6/10 Exceptional! (394 reviews)
One of a kind

Reviewed on Oct 29, 2026

The Tree House Boutique Hotel

The Tree House Boutique Hotel

5 out of 5
Cape Town City Centre
Price was $3,941, price is now $3,097 per person
$3,097
per person
Dec 7 - Dec 14
just found
Roundtrip non-stop flight included
New York (JFK) to Cape Town (CPT)
9.6/10 Exceptional! (243 reviews)
Lovely stay, great hotel and fantastic location

Reviewed on Oct 23, 2026

Labotessa Luxury Boutique Hotel

Labotessa Luxury Boutique Hotel

5 out of 5
Cape Town City Centre
Price was $4,283, price is now $3,511 per person
$3,511
per person
Dec 7 - Dec 14
just found
Roundtrip non-stop flight included
New York (JFK) to Cape Town (CPT)
10/10 Exceptional! (43 reviews)
Amazing experience. Really feels like home. Well worth the price. Only thing maybe is to improve the quality of the happy hour bar snacks and food which was not that great. Otherwise amazing.

Reviewed on Jul 15, 2026

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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

$55
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

$117
per traveler
92% of travellers recommend
Cape Town Full Day Cape Winelands Tour
Cape town Big Five Sunset Safari with food and transport

Aquila Big Five Sunset Safari with food and transport

$173
per adult
Aquila Big Five Sunset Safari with food and transport
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
$155 nightly
The price is $178 total per night from Nov 3 to Nov 4
$178 total
Nov 3 - Nov 4
Total with taxes and 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.
Devonvale Golf & Wine Estate

Devonvale Golf & Wine Estate

4 out of 5
Bottelary Road Stellenbosch Western Cape
$174 nightly
The price is $200 total per night from Dec 2 to Dec 3
$200 total
Dec 2 - Dec 3
Total with taxes and fees
8.8/10 Excellent! (129 reviews)
"The property location was perfect for visiting wineries near Stellenbosch. The room was spacious and comfortable with a wonderful balcony overlooking the gardens/courtyard. Breakfast at the clubhouse was amazing — well prepared, and very tasty, but the portions were a bit large."

Reviewed on Oct 14, 2026

Devonvale Golf & Wine Estate
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.

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 $2,792 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.