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.
Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER

3 out of 5
Save 100% on your flight
Price was $1,809, price is now $1,117 per person
$1,117
per person
Feb 25 - Mar 2
found 15 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Kahului (OGG)
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 our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.

Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
South Kihei
Price was $3,510, price is now $1,569 per person
$1,569
per person
Mar 31 - Apr 6
found 18 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)
Book a stay at this beach hotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the property condition in our reviews. Popular attractions Wailea Beach and Keawakapu Beach North are located nearby.

Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $2,681, price is now $1,328 per person
$1,328
per person
Mar 31 - Apr 6
found 18 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)
Stay at this 3-star beach condo in Kahana. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.

Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
Price was $2,951, price is now $1,673 per person
$1,673
per person
Mar 31 - Apr 6
found 18 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)
Stay at this condo in Kahana. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Kaanapali Beach and Napili Bay are located nearby.

Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Save 100% on your flight
Price was $2,549, price is now $1,489 per person
$1,489
per person
Mar 31 - Apr 6
found 16 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, free parking, and a garden. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,846, price is now $1,693 per person
$1,693
per person
Mar 31 - Apr 6
found 18 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)
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 rooms in our reviews. Popular attractions Kaanapali Beach and Whalers Village are located nearby.

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Top Hotel Deals

Gods Peace Of Maui

Gods Peace Of Maui

2 out of 5
1290 Haliimaile Rd Makawao HI
15.94 km from city center
Book a stay at this spa B&B in Makawao. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Haliʻimaile Farmer's Market and Hui Noʻeau Visual ...
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4.5 out of 5
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 ...
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
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 ...
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
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 ...
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
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 ...
Maui Coast Hotel

Maui Coast Hotel

3.5 out of 5
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 3 hot tubs. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Maui Seaside Hotel

Maui Seaside Hotel

3 out of 5
100 W Kaahumanu Ave Kahului HI
28.2 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 ...
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
3550 Wailea Alanui Dr Kihei HI
22.02 km from city center
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 5 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

3.5 out of 5
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 ...
Maui Beach Hotel

Maui Beach Hotel

3 out of 5
170 W Kaahumanu Avenue Kahului HI
28.29 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 ...
Sheraton Maui Resort & Spa

Sheraton Maui Resort & Spa

4 out of 5
2605 Kaanapali Pkwy Lahaina HI
50.81 km from city center
Book a stay at this beach resort in Kaanapali. Enjoy a full-service spa, 5 restaurants, and a beach locale. Our guests praise the helpful staff in our reviews. ...
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
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 ...
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
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 Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy Lahaina HI
51.37 km from city center
Book a stay at this beach aparthotel in Kaanapali. Enjoy 2 outdoor pools, a full-service spa, and a beach locale. Our guests praise the pool and the restaurant ...
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4 out of 5
130 Kai Malina Parkway Lahaina HI
51.32 km from city center
Book a stay at this beach condo in Kaanapali. Enjoy free WiFi, free valet parking, and 4 outdoor pools. Our guests praise the helpful staff and the clean rooms ...
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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.

Alaska Airlines
Tue, Mar 10 - Wed, Mar 11
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Mar 10 from Daniel K. Inouye Intl. to Kahului, returning Wed, Mar 11, priced at $73 found 1 day ago
Hawaiian Airlines
Wed, Mar 4 - Tue, Mar 10
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$78 Roundtrip, found 11 hours ago
$78
Roundtrip
found 11 hours ago
Select Hawaiian Airlines flight, departing Wed, Mar 4 from Daniel K. Inouye Intl. to Kahului, returning Tue, Mar 10, priced at $78 found 11 hours ago
Southwest Airlines
Wed, Mar 4 - Tue, Mar 10
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$78 Roundtrip, found 11 hours ago
$78
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Wed, Mar 4 from Daniel K. Inouye Intl. to Kahului, returning Tue, Mar 10, priced at $78 found 11 hours ago
Delta
Mon, Mar 23 - Wed, Apr 1
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$288 Roundtrip, found 6 days ago
$288
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Mar 23 from Seattle - Tacoma Intl. to Kahului, returning Wed, Apr 1, priced at $288 found 6 days ago
United
Mon, Apr 27 - Fri, May 1
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$401 Roundtrip, found 6 days ago
$401
Roundtrip
found 6 days ago
Select United flight, departing Mon, Apr 27 from Seattle - Tacoma Intl. to Kahului, returning Fri, May 1, priced at $401 found 6 days ago