Upcountry Maui Vacation Packages for 2026
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 $1,807, price is now $1,001 per person
$1,001
per person
Mar 5 - Mar 12
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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.
The Gardens at West Maui
Save 100% on your flight
Price was $2,219, price is now $1,166 per person
$1,166
per person
Mar 5 - Mar 12
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Kahului (OGG)
Stay at this condo in Napili. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
OUTRIGGER Kaanapali Beach Resort
Save 100% on your flight
Price was $2,797, price is now $1,641 per person
$1,641
per person
Mar 5 - Mar 12
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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.
Fairmont Kea Lani Maui
Wailea
Save 100% on your flight
Price was $4,935, price is now $3,134 per person
$3,134
per person
Mar 5 - Mar 12
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Kahului (OGG)
Book a stay at this luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
The Whaler Resort Kaanapali Beach
Save 100% on your flight
Price was $3,479, price is now $2,240 per person
$2,240
per person
Mar 5 - Mar 12
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Kahului (OGG)
Book a stay at this beach condo in Kaanapali. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
Maui Beach Vacation Club
North Kihei
Save 100% on your flight
Price was $2,266, price is now $1,505 per person
$1,505
per person
Mar 5 - Mar 12
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. 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.
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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 ...
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 ...
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 ...
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 ...
Maui Coast Hotel
2259 S Kihei Rd Kihei HI
21.75 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 ...
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 ...
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 ...
Fairmont Kea Lani Maui
4100 Wailea Alanui Dr Kihei HI
22.47 km from city center
Book a stay at this luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
Sheraton Maui Resort & Spa
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. ...
Maui Seaside Hotel
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 ...
Maui Beach Hotel
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 ...
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 ...
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 ...
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.
Tue, Feb 17 - Thu, Feb 19
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Tue, Feb 17 - Wed, Feb 18
YVR
Vancouver Intl.
OGG
Kahului
$260 Roundtrip, found 1 day ago
$260
Roundtrip
found 1 day ago
Tue, Feb 17 - Tue, Feb 24
LAX
Los Angeles Intl.
OGG
Kahului
$263 Roundtrip, found 3 days ago
$263
Roundtrip
found 3 days ago
Mon, Feb 2 - Mon, Feb 16
LAX
Los Angeles Intl.
OGG
Kahului
$278 Roundtrip, found 3 days ago
$278
Roundtrip
found 3 days ago
Tue, Feb 3 - Fri, Feb 13
LAX
Los Angeles Intl.
OGG
Kahului
$288 Roundtrip, found 4 days ago
$288
Roundtrip
found 4 days ago