Wellington Vacations from $2,300

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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.
Silver Forest Boutique Hotel and Spa

Silver Forest Boutique Hotel and Spa

4 out of 5
Somerset West
Price was $2,624, price is now $2,300 per person
$2,300
per person
Aug 16 - Aug 22
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Cape Town (CPT)
9.4/10 Exceptional! (24 reviews)
Everything about the property is 5 star ,from the rooms,restaurants the owner and all the staff.best little hidden gem in the area

Reviewed on Jan 6, 2025

Taaibosch Collection

Taaibosch Collection

3.5 out of 5
Price was $6,013, price is now $4,682 per person
$4,682
per person
Aug 16 - Aug 22
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Cape Town (CPT)
No reviews
Sante Wellness Retreat & Spa

Sante Wellness Retreat & Spa

5 out of 5
Price was $3,884, price is now $3,134 per person
$3,134
per person
Aug 16 - Aug 22
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Cape Town (CPT)
9.6/10 Exceptional! (35 reviews)
Really lovely hotel, wonderful staff and beautiful spa. Rooms are gorgeous too

Reviewed on May 19, 2026

The Winchester Hotel by NEWMARK

The Winchester Hotel by NEWMARK

4 out of 5
Sea Point
Price was $3,547, price is now $3,066 per person
$3,066
per person
Aug 16 - Aug 22
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Cape Town (CPT)
9.2/10 Wonderful! (337 reviews)
Great location and amazing boutique feel hotel. Loved it all

Reviewed on May 18, 2026

Nova Constantia Boutique Residence

Nova Constantia Boutique Residence

5 out of 5
Constantia
Price was $2,800, price is now $2,466 per person
$2,466
per person
Aug 16 - Aug 22
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Cape Town (CPT)
9.6/10 Exceptional! (98 reviews)
Impeccable service and peaceful, beautiful surroundings.

Reviewed on May 28, 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

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

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

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

$118
per traveler
92% of travellers recommend
Cape Town Full Day Cape Winelands Tour
Aquila Afternoon Safari and Wine Tasting

Cape Town: Sunset Safari & Wine Tasting Adventure*

$110
per adult
Cape Town: Sunset Safari & Wine Tasting Adventure*
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
$143 nightly
The price is $164 total per night from May 31 to Jun 1
$164 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (67 reviews)
"Very nice pool and super friendly staff"

Reviewed on Mar 18, 2026

Val Du Charron Wine & Leisure Estate
Boschendal Farm Estate

Boschendal Farm Estate

4.5 out of 5
Pniel Road Franschhoek Western Cape
$327 nightly
The price is $379 total per night from Jun 11 to Jun 12
$379 total
Jun 11 - Jun 12
Total with taxes and fees
9.4/10 Exceptional! (173 reviews)
"Property very beautiful a big. Rooms are not very clean and need some maintenance."

Reviewed on Apr 21, 2026

Boschendal Farm Estate
Clouds Estate

Clouds Estate

5 out of 5
Helshoogte Road Stellenbosch Western Cape
$191 nightly
The price is $221 total per night from Jun 21 to Jun 22
$221 total
Jun 21 - Jun 22
Total with taxes and fees
9.6/10 Exceptional! (297 reviews)
"Great location Beautiful views Staff amazing, did all they could to accommodate any requests Villa 14 didnt meet my expectations unfortunately. Needs renovating and the ant infestation was a problem. Bedroom lacked a mirror and is small in comparison to lounge. I would have liked a slightly larger ..."

Reviewed on May 15, 2026

Clouds Estate
See all 403 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 $2,300 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.