Search Deals onSouth Shore Vacation Packages
South Shore Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Plantation Hale Suites
per person
Aug 10 - Aug 16
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lihue (LIH)
Book a stay at this business-friendly aparthotel in Kapaa. Enjoy 3 outdoor pools, 2 hot tubs, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Coconut Marketplace and Waipouli Beach are located nearby.

Banyan Harbor Resort
per person
Aug 10 - Aug 16
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lihue (LIH)
Stay at this aparthotel in Lihue. Enjoy a 24-hour business center, laundry facilities, and concierge services. Our guests praise the helpful staff in our reviews. Popular attractions Nawiliwili Harbor and Nawiliwili Park are located nearby.

Ko'a Kea Resort on Po'ipu Beach
Save 100% on your flight
per person
Aug 10 - Aug 16
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lihue (LIH)
Stay at this 4.5-star luxury resort in Koloa. Enjoy a full-service spa, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Poipu Beach and ʻAuliʻi Lūʻau are located nearby.

1 Hotel Hanalei Bay
Save 100% on your flight
per person
Aug 10 - Aug 16
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lihue (LIH)
Stay at this 5-star luxury resort in Princeville. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Hanalei Bay and Puupoa Beach are located nearby.

Aston Islander on the Beach
per person
Aug 10 - Aug 16
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lihue (LIH)
Book a stay at this beach hotel in Kapaa. Enjoy a beach locale, laundry facilities, and a picnic area. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Coconut Marketplace and Waipouli Beach are located nearby.

Hanalei Bay Resort
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lihue (LIH)
Stay at this 3-star condo in Princeville. Enjoy free WiFi, 2 outdoor pools, and a free beach shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Hanalei Bay and Princeville Golf Club Prince Course are located nearby.

Makai Club Resort
per person
Aug 10 - Aug 16
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lihue (LIH)
Stay at this 3.5-star golf condo in Princeville. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Hanalei Bay and Princeville Makai Golf Club are located nearby.

Castle Kiahuna Plantation & Beach Bungalows
per person
Aug 10 - Aug 16
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lihue (LIH)
Stay at this 3-star beach aparthotel in Koloa. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the property condition in our reviews. Popular attractions Poipu Beach and Poipu Shopping Village are located nearby.
South Shore Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



South Shore Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Jul 1 - Wed, Jul 2
HNL
Daniel K. Inouye Intl.
LIH
Lihue
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago

Thu, Sep 4 - Mon, Sep 8
CLD
McClellan-Palomar
LIH
Lihue
$255 Roundtrip, found 6 days ago
$255
Roundtrip
found 6 days ago

Mon, Nov 3 - Mon, Nov 10
SFO
San Francisco Intl.
LIH
Lihue
$303 Roundtrip, found 2 days ago
$303
Roundtrip
found 2 days ago

Mon, Sep 1 - Thu, Sep 18
SJC
Norman Y. Mineta San Jose Intl.
LIH
Lihue
$312 Roundtrip, found 14 hours ago
$312
Roundtrip
found 14 hours ago
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