Upcountry Maui Vacation Packages for 2026

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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
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 ...
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 ...
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 ...
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 ...
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

4 out of 5
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 ...
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 ...
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 2 restaurants. 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
28.23 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 ...
Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui

4 out of 5
104 Ka'anapali Shores Place Kaanapali HI
51.44 km from city center
Book a stay at this beach hotel in Kaanapali. Enjoy a beach locale, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the ...
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 ...
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 ...
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
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 ...
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 ...
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
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 ...
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 ...
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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
Tue, Sep 29 - Wed, Sep 30
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$133 Roundtrip, just found
$133
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Sep 29 from Daniel K. Inouye Intl. to Kahului, returning Wed, Sep 30, priced at $133 just found
Alaska Airlines
Tue, Sep 29 - Wed, Sep 30
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$145 Roundtrip, just found
$145
Roundtrip
just found
Select Alaska Airlines flight, departing Tue, Sep 29 from Daniel K. Inouye Intl. to Kahului, returning Wed, Sep 30, priced at $145 just found
Southern Airways Express
Fri, Oct 2 - Tue, Oct 6
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago
Select Southern Airways Express flight, departing Fri, Oct 2 from Daniel K. Inouye Intl. to West Maui, returning Tue, Oct 6, priced at $198 found 3 days ago
United
Thu, Aug 27 - Wed, Sep 2
LAX
Los Angeles Intl.
OGG
Kahului
$297 Roundtrip, found 6 days ago
$297
Roundtrip
found 6 days ago
Select United flight, departing Thu, Aug 27 from Los Angeles Intl. to Kahului, returning Wed, Sep 2, priced at $297 found 6 days ago
American Airlines
Thu, Aug 27 - Wed, Sep 2
LAX
Los Angeles Intl.
OGG
Kahului
$297 Roundtrip, found 6 days ago
$297
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Aug 27 from Los Angeles Intl. to Kahului, returning Wed, Sep 2, priced at $297 found 6 days ago