Upcountry Maui Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Upcountry Maui Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Kahana Villa
Save 100% on your flight
Price was $2,368, price is now $1,291 per person
$1,291
per person
Jan 4 - Jan 10
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
Stay at this 3-star condo in Kahana. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Sands of Kahana
Save 100% on your flight
Price was $2,558, price is now $1,373 per person
$1,373
per person
Jan 4 - Jan 10
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
Stay at this 3-star beach aparthotel in Kahana. Enjoy free parking, a beach locale, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Save 100% on your flight
Price was $4,209, price is now $2,353 per person
$2,353
per person
Jan 4 - Jan 10
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
Stay at this 5-star luxury resort in Kihei. Enjoy 3 restaurants, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
Royal Lahaina Bungalows & Spa
Save 100% on your flight
Price was $2,494, price is now $1,486 per person
$1,486
per person
Jan 4 - Jan 10
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
Stay at this 5-star luxury aparthotel in Lahaina. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
Royal Lahaina Resort & Bungalows
Save 100% on your flight
Price was $2,227, price is now $1,361 per person
$1,361
per person
Jan 4 - Jan 10
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
Stay at this 4-star beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
OUTRIGGER Kaanapali Beach Resort
Save 100% on your flight
Price was $2,413, price is now $1,483 per person
$1,483
per person
Jan 4 - Jan 10
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
Stay at this 3.5-star 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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Gods Peace Of Maui
1290 Haliimaile Rd, Makawao, HI
15.88 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 ...
Maui Coast Hotel
2259 S Kihei Rd, Kihei, HI
21.75 km from city center
Stay at this 3.5-star 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 ...
Royal Lahaina Resort & Bungalows
2780 Kekaa Dr, Lahaina, HI
50.81 km from city center
Stay at this 4-star beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the bar and the helpful staff in our ...
OUTRIGGER Kaanapali Beach Resort
2525 Kaanapali Parkway, Lahaina, HI
50.66 km from city center
Stay at this 3.5-star beach resort in Kaanapali. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive, Kihei, HI
22.07 km from city center
Stay at this 5-star 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
2365 Kaanapali Pkwy, Lahaina, HI
50.61 km from city center
Stay at this 4.5-star 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
1 Ritz-Carlton Drive, Kapalua, HI
50.89 km from city center
Stay at this 5-star luxury resort in Kapalua. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
Hilton Vacation Club Ka'anapali Beach Maui
104 Ka'anapali Shores Place, Kaanapali, HI
51.39 km from city center
Stay at this 4-star beach hotel in Kaanapali. Enjoy a beach locale, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the ...
Hyatt Regency Maui Resort & Spa
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 ...
Wailea Beach Resort - Marriott, Maui
3700 Wailea Alanui Dr, Kihei, HI
21.93 km from city center
Stay at this 4.5-star luxury resort in Kihei. Enjoy 4 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
Maui Seaside Hotel
100 W Kaahumanu Ave, Kahului, HI
28.2 km from city center
Stay at this 3-star beach hotel in Kahului. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the pool and the restaurant in our ...
Sheraton Maui Resort & Spa
2605 Kaanapali Pkwy, Lahaina, HI
50.81 km from city center
Stay at this 4-star beach resort in Kaanapali. Enjoy a full-service spa, 5 restaurants, and a beach locale. Our guests praise the helpful staff in our reviews. ...
Andaz Maui at Wailea Resort - a concept by Hyatt
3550 Wailea Alanui Dr, Kihei, HI
21.89 km from city center
Stay at this 4.5-star 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 ...
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.
Sat, Aug 15 - Tue, Aug 25
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Sun, Nov 30 - Sun, Dec 7
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$258 Roundtrip, found 2 days ago
$258
Roundtrip
found 2 days ago
Wed, Dec 3 - Tue, Dec 9
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$358 Roundtrip, found 2 days ago
$358
Roundtrip
found 2 days ago
Wed, Dec 3 - Tue, Dec 9
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$372 Roundtrip, found 2 days ago
$372
Roundtrip
found 2 days ago