Wellington Holidays

Photo by T. R. Filbin

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Top hotels in Wellington

Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road Slade KY
Fully refundableReserve now, pay when you stay
The price is S$136 per night from 23 Aug to 24 Aug
S$136
23 Aug - 24 Aug
includes taxes & fees
8.6/10 Excellent! (1,969 reviews)
"Outdated cottage in need of repair."

Reviewed on 22 Jul, 2026

Natural Bridge State Resort Park
Best Western Eagles Inn

Best Western Eagles Inn

2.5 out of 5
110 Toms Dr Morehead KY
Fully refundableReserve now, pay when you stay
The price is S$195 per night from 6 Aug to 7 Aug
S$195
6 Aug - 7 Aug
includes taxes & fees
8.8/10 Excellent! (815 reviews)
"Very clean and friendly staff loved the new coffee machine 👌 😀 breakfast was good also"

Reviewed on 23 Jul, 2026

Best Western Eagles Inn
Black Bear Lodge Motel

Black Bear Lodge Motel

2.5 out of 5
781 Natural Bridge Rd Slade KY
Fully refundableReserve now, pay when you stay
The price is S$125 per night from 26 Jul to 27 Jul
S$125
26 Jul - 27 Jul
includes taxes & fees
8/10 Very good! (691 reviews)
"Good location. No ice. Helpful if you get locked out. Inconvenient check in and out. Would not be my first choice."

Reviewed on 10 Jul, 2026

Black Bear Lodge Motel
See all 912 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.

Stay near popular Wellington attractions

Red River Gorge

9.6/10 (460 reviews)
Explore the great outdoors at Red River Gorge, a popular spot to commune with nature in Wellington. Amble around this relaxing area's riverfront or seek out the hiking trails.
See properties

Frequently asked questions

How much does a Wellington holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Wellington costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Wellington?
You're likely to find lower rates and better availability in September, November and December. Take a look at our cheap Wellington holiday packages and you could score some great off-season discounts.
How many days is enough for Wellington?
The ideal duration of your Wellington holiday depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to hit all the leading attractions and discover some hidden gems along the way.
How to find the best Wellington package deals?
Use Expedia's filter tool to find some fabulous Wellington package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Wellington package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Wellington holiday as a package?
An Expedia holiday package could land you great savings when compared to booking hotels and flights individually. Better still, you can personalise your Wellington trip to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Wellington?
If you have your Wellington holiday dates finalized, book as early as you can to bag some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Wellington?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Wellington.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodation will probably be the largest expense during your trip to Wellington.
  3. Work out your trip length: Consider how much time you want to spend exploring Wellington. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalised Wellington holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.