Search Deals onWestport Vacation Packages
Westport Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.


Chebeague Island Inn
per person
Jun 6 - Jun 10
found 2 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Portland (PWM)
Stay at this 4-star beach hotel in Chebeague Island. Enjoy free WiFi, breakfast (surcharge), and a free ferry terminal shuttle. Popular attractions Little John Island Preserve and Winslow Memorial Park are located nearby.

Hilton Garden Inn Portland Downtown Waterfront
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.

Cliff House Maine
Save 100% on your flight
per person
May 7 - May 11
found 16 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Stay at this 4.5-star luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Perkins Cove and Marginal Way are located nearby.

White Barn Inn & Spa, Auberge Resorts Collection
Save 100% on your flight
per person
May 7 - May 11
found 16 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Stay at this 5-star luxury hotel in Kennebunk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions St. Anthony's Franciscan Monastery and Kennebunkport Village Green are located nearby.

Portland Harbor Hotel
per person
Jun 6 - Jun 10
found 2 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.

Inn By The Sea
Save 100% on your flight
per person
Jun 6 - Jun 10
found 2 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Portland (PWM)
Stay at this 4-star beach hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.

Blind Tiger Portland – Carleton Street
per person
Jun 6 - Jun 10
found 2 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.
Westport Vacation Packages 3-4 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.

Fri, Apr 4 - Mon, Apr 7
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago

Sat, Mar 22 - Sat, Mar 29
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago

Fri, Apr 4 - Thu, Apr 10
LGA
LaGuardia
PWM
Portland Intl. Jetport
$133 Roundtrip, found 5 days ago
$133
Roundtrip
found 5 days ago

Mon, Mar 31 - Fri, Apr 4
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
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