Upcountry Maui Vacation Packages for 2026

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Upcountry Maui Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Maui Beach Hotel

Maui Beach Hotel

$773
per person
Oct 15 - Oct 19
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this beach hotel in Kahului. Enjoy a beach locale, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ho'aloha Park and Queen Ka’ahumanu Center are located nearby.
Maui Beach Vacation Club

Maui Beach Vacation Club

North Kihei
$1,297
per person
Oct 15 - Oct 19
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters are located nearby.
The building was right at the street. Too much driving car noise. There was no house keeping available. Across street was the beach but not appropriate for swimming

Reviewed on Sep 11, 2026

Lahaina Shores Beach Resort By Castle

Lahaina Shores Beach Resort By Castle

$853
per person
Oct 15 - Oct 19
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this beach apartment in Lahaina. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Kaanapali Beach and Whalers Village are located nearby.
Everything we needed for our stay in Maui! Spectacular on the beach location and views. The unit had all the big and little things we needed. Look forward to returning.

Reviewed on Aug 31, 2026

Maui Banyan Vacation Club

Maui Banyan Vacation Club

South Kihei
$962
per person
Oct 15 - Oct 19
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
Very nice room. Amazing stay!

Reviewed on Sep 9, 2026

Aston Maui Hill

Aston Maui Hill

South Kihei
$1,106
per person
Oct 15 - Oct 19
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Stay at this aparthotel in Kihei. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Kihei Boat Ramp are located nearby.
Aston at the Maui Banyan

Aston at the Maui Banyan

South Kihei
$947
per person
Oct 15 - Oct 19
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this beach hotel in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
The main bedroom AC was not enough for the room was hot

Reviewed on Aug 30, 2026

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Top Hotel Deals

Gods Peace Of Maui

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI
15.94 km from city center
Stay at this B&B in Makawao. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Haliʻimaile Farmer's Market and Hui Noʻeau Visual Arts Center ...
Maui Coast Hotel

Maui Coast Hotel

2259 S Kihei Rd Kihei HI
21.58 km from city center
Stay at this hotel in Kihei. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

200 Nohea Kai Dr Lahaina HI
50.51 km from city center
Book a stay at this beach resort in Kaanapali. Enjoy free WiFi, 6 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the property ...
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI
22.07 km from city center
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy Lahaina HI
50.61 km from city center
Book a stay at this luxury hotel in Kaanapali. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property ...
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

1 Ritz-Carlton Drive Kapalua HI
50.89 km from city center
Book a stay at this luxury resort in Kapalua. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr Lahaina HI
50.81 km from city center
Book a stay at this beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
Aston Kaanapali Shores

Aston Kaanapali Shores

3445 Lower Honoapiilani Hwy Lahaina HI
51.51 km from city center
Book a stay at this beach aparthotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in ...
Maui Beach Hotel

Maui Beach Hotel

170 W Kaahumanu Avenue Kahului HI
28.4 km from city center
Book a stay at this beach hotel in Kahului. Enjoy a beach locale, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and ...
Maui Seaside Hotel

Maui Seaside Hotel

100 W Kaahumanu Ave Kahului HI
28.23 km from city center
Book a stay at this beach hotel in Kahului. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the pool and the restaurant in our ...
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI
22.43 km from city center
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

2525 Kaanapali Parkway Lahaina HI
50.66 km from city center
Book a stay at this beach resort in Kaanapali. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr Kihei HI
21.93 km from city center
Book a stay at this luxury resort in Kihei. Enjoy 4 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in ...
Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

110 Ka'anapali Shores Place Kaanapali HI
51.45 km from city center
Book a stay at this beach aparthotel in Kaanapali. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the property condition ...
Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER

5315 Lower Honoapiilani Rd Lahaina HI
51.53 km from city center
Book a stay at this beach aparthotel in Napili. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Alaska Airlines
Southern Airways Express
United
Delta
Tue, Sep 29 - Thu, Oct 8
SJC
Norman Y. Mineta San Jose Intl.
OGG
Kahului
$353
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 29 from Norman Y. Mineta San Jose Intl. to Kahului, returning Thu, Oct 8, priced at $353 found 4 days ago