Upcountry Maui Holidays

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Upcountry Maui Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sands of Kahana

Sands of Kahana

3 out of 5
Price was S$5,080, price is now S$3,462 per person
S$3,462
per person
9 Feb - 14 Feb
found 21 hours ago
Return flight included
Singapore (SIN) to Kahului (OGG)
8.2/10 Very Good! (453 reviews)
Really enjoyed our stay. Didn’t realize we’d have a washer/dryer in unit and our 1 bedroom had two full baths!

Reviewed on 4 Dec, 2025

Hyatt Vacation Club at Ka'anapali Beach, Maui

Hyatt Vacation Club at Ka'anapali Beach, Maui

3.5 out of 5
Save 100% on your flight
Price was S$7,387, price is now S$5,023 per person
S$5,023
per person
9 Feb - 14 Feb
found 21 hours ago
Return flight included
Singapore (SIN) to Kahului (OGG)
9.2/10 Wonderful! (69 reviews)
Staff was very accommodating!

Reviewed on 1 Dec, 2025

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Price was S$6,904, price is now S$4,900 per person
S$4,900
per person
9 Feb - 14 Feb
found 21 hours ago
Return flight included
Singapore (SIN) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive!

Reviewed on 27 Aug, 2025

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Price was S$5,313, price is now S$3,801 per person
S$3,801
per person
9 Feb - 14 Feb
found 21 hours ago
Return flight included
Singapore (SIN) to Kahului (OGG)
9.6/10 Exceptional! (292 reviews)
Beautiful room with views of the beach and black rock. We used the cooking facilities and everything you need was there. Great pillows. Our only complaint was the light over the dining table was so low it was easy to hit your head on it when standing up.

Reviewed on 17 Dec, 2025

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
Save 100% on your flight
Price was S$8,439, price is now S$6,207 per person
S$6,207
per person
9 Feb - 14 Feb
found 21 hours ago
Return flight included
Singapore (SIN) to Kahului (OGG)
9/10 Wonderful! (1,001 reviews)
The breakfast menus were fresh everyday.

Reviewed on 5 Dec, 2025

Top hotels in Upcountry Maui

Gods Peace Of Maui

Gods Peace Of Maui

2 out of 5
1290 Haliimaile Rd Makawao HI
The price is S$225 per night from 25 Dec to 26 Dec
S$225
25 Dec - 26 Dec
includes taxes & fees
8.6/10 Excellent! (50 reviews)
Loved the hibiscus eoom

Reviewed on 8 Dec, 2025

Gods Peace Of Maui
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
2780 Kekaa Dr Lahaina HI
Fully refundableReserve now, pay when you stay
The price is S$373 per night from 21 Dec to 22 Dec
S$373
21 Dec - 22 Dec
includes taxes & fees
8.4/10 Very Good! (1,584 reviews)
Highly recommend!

Reviewed on 15 Dec, 2025

Royal Lahaina Resort & Bungalows
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4.5 out of 5
2365 Kaanapali Pkwy Lahaina HI
The price is S$709 per night from 4 Jan to 5 Jan
S$709
4 Jan - 5 Jan, 2026
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
The pool, the amenities, and the beach area restaurants were all nothing short of spectacular. The view from our ocean view room was breathtaking, and we felt very safe throughout the hotel. The beautiful birds, specifically the flamingos and parrots that guests can interact with, were fun attractions ...

Reviewed on 18 Dec, 2025

The Westin Maui Resort & Spa, Ka'anapali
See all 13,208 properties in Upcountry Maui
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.

Frequently asked questions

Can I cancel my flight booking to Upcountry Maui due to COVID-19?
Our handy Customer Service Portal is your one-stop shop for most travel queries, including about flight changes related to COVID-19. For greater peace of mind, read through the terms and conditions of your airfare before booking your tickets.
What's the best way to find cheap flights to Upcountry Maui that have flexible change policies?
We understand that travel schedules can change in a flash, so reserving a flexible fare with Expedia makes good sense. Tick the "No change fee" box under the "Flexible change policies" filter. Your low-priced, flexible flight to Upcountry Maui is just a few clicks away.
What are some of the general tips for travellers to Upcountry Maui during the COVID-19 outbreak?
If it's your first time travelling during COVID-19, you'll notice a host of new standards and rules in place. Take note of these tips and make your journey to Upcountry Maui go off without a hitch:
  • Find out if any travel restrictions apply to your destination and origin before booking anything. Also check if there are any special conditions you'll have to follow on arrival, such as health testing.
  • When you pass through airport screening, keep your face mask on. You will be asked to lower it briefly for identification purposes. Passengers who refuse to wear a mask may be fined and denied entry.
  • To reduce the potential of cross-contamination, place your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA employee.
  • You're permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on bag. You'll have to remove it for X-ray scanning.
  • Empty your personal items from your pockets, like your wallet, coins and keys, and put them in your carry-on instead of into bins. This will reduce handling during the screening process.
  • If you're taking food through the security checkpoint, put it in a clear plastic bag and then into a screening bin. This reduces the likelihood that a TSA employee will need to touch your food container or carry-on bag for closer inspection.

Which airlines fly to Upcountry Maui?
Arrange your airfare with Hawaiian Airlines and start working on your Upcountry Maui travel itinerary. This well-known airline offers 1202 flights every month to Kahului Airport (OGG), a main gateway.
How can I find cheap tickets to Upcountry Maui?
To pick up an awesome deal to Upcountry Maui, book well ahead. Also use Expedia's handy "flexible dates" feature at the top of your search results. This will compare the cheapest prices for similar time frames. In the last seven days, was the best price for a flight to Upcountry Maui.
How much is a flight to Upcountry Maui?
In the last seven days, round-trip flights to Upcountry Maui sold for as little as and peaked at . For one-way trips out of (), the lowest amount paid during this same period was just .
What are the most popular airports to fly into in Upcountry Maui?
Upcountry Maui's main airport is Kahului Airport (OGG). Get your amazing journey underway by securing a fare on one of the 3826 flights every month to this destination.
When is the cheapest time to fly to Upcountry Maui?
Leave earlier in the week to book a bargain airfare to Upcountry Maui. Tuesday is normally the most economical day to fly, with Monday running a close second. Saturday typically has the highest ticket prices. This is because many travellers like to start their trip on a weekend.
How much is a plane ticket to Upcountry Maui?
In the last seven days, seats ranged between and . Swipe through our awesome deals to Upcountry Maui, make a booking and then get ready for your getaway!
Which airlines with flights to Upcountry Maui employ COVID-19 cleanliness policies?
While flying during the COVID-19 pandemic can be nerve-wracking, airlines are doing their bit to ensure the well-being of all on board. These are a few carriers that have introduced changes:
  • Hawaiian Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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* 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.