Vacations Close To The Skyline Trail

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The Skyline Trail Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,004, price is now $1,309 per person
$1,309
per person
May 8 - May 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)

Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
Price was $3,413, price is now $2,231 per person
$2,231
per person
May 7 - May 13
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $3,177, price is now $2,140 per person
$2,140
per person
May 8 - May 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)

Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $2,330, price is now $1,570 per person
$1,570
per person
May 8 - May 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)

Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
Price was $3,047, price is now $2,108 per person
$2,108
per person
May 7 - May 13
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)

Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
Price was $2,958, price is now $2,052 per person
$2,052
per person
May 7 - May 13
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was $2,484, price is now $1,771 per person
$1,771
per person
May 8 - May 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)

Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Save 100% on your flight
Price was $2,315, price is now $1,678 per person
$1,678
per person
May 7 - May 13
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)

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Best Lodging Options Near The Skyline Trail

Hana-Maui Resort, a Destination by Hyatt Residence

Hana-Maui Resort, a Destination by Hyatt Residence

4 out of 5
5031 Hana Hwy Hana HI
17.87 km from The Skyline Trail
Book a stay at this spa resort in Hana. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Gods Peace Of Maui

Gods Peace Of Maui

2 out of 5
1290 Haliimaile Rd Makawao HI
24.76 km from The Skyline Trail
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 ...
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
30.11 km from The Skyline Trail
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

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
30.06 km from The Skyline Trail
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 ...
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr Kihei HI
29.85 km from The Skyline Trail
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 ...
Maui Coast Hotel

Maui Coast Hotel

3.5 out of 5
2259 S Kihei Rd Kihei HI
30.26 km from The Skyline Trail
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 ...
Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

3.5 out of 5
1813 Baldwin Ave Makawao HI
27.05 km from The Skyline Trail
Book a stay at this boutique hotel in Makawao. Enjoy free breakfast, onsite spa services, and a garden. Popular attractions Haliʻimaile Farmer's Market and Maui ...
Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea

3.5 out of 5
75 Wailea Ike Kihei HI
29.26 km from The Skyline Trail
Book a stay at this business-friendly hotel in Kihei. Enjoy free breakfast, a free beach shuttle, and a 24-hour fitness center. Our guests praise the helpful ...
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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.