Search Deals onLong Island Vacation Packages
Long Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Portland Regency Hotel & Spa
Price was $579, price is now $493 per person
$493
per person
Jan 27 - Jan 30
found 4 hours ago
Roundtrip flight included
Raleigh (RDU) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.
Blind Tiger Portland - Danforth Street.
Price was $2,849, price is now $2,217 per person
$2,217
per person
Dec 26 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions State Theatre and Cross Insurance Arena are located nearby.
The Docent's Collection at 121 Middle Street
Price was $1,897, price is now $1,544 per person
$1,544
per person
Dec 26 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions State Theatre and Thompson's Point are located nearby.
Our only place to stay in Portland!
Reviewed on Nov 14, 2026
Blind Tiger Portland – Carleton Street
Price was $1,568, price is now $1,288 per person
$1,288
per person
Dec 26 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions State Theatre and Cross Insurance Arena are located nearby.
Inn By The Sea
Price was $1,964, price is now $1,613 per person
$1,613
per person
Dec 26 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
84 Main
Price was $1,322, price is now $1,096 per person
$1,096
per person
Dec 20 - Dec 23
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Kennebunk Free Library are located nearby.
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.
Reviewed on Jul 17, 2026
Portland Harbor Hotel
Price was $1,252, price is now $1,042 per person
$1,042
per person
Dec 26 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.
Old hotel recently updated. Great location in Old Port in walking distance of restaurants and shop. Very helpful staff. Easy valet parking. They charge a resort fee but you get it back as credit to use for breakfast or at the bar. Great outdoor patio area with gas fire pit. Great vibe for adult travelers.
Reviewed on Nov 14, 2026
Canopy by Hilton Portland Waterfront
Price was $639, price is now $546 per person
$546
per person
Jan 27 - Jan 30
found 4 hours ago
Roundtrip flight included
Raleigh (RDU) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.
They forgot to clean the room one night. Mistake which compensated pro perla
Reviewed on Nov 14, 2026
Long Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Long Island 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.
Mon, Feb 15 - Sat, Feb 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$224 Roundtrip, found 11 hours ago
$224
Roundtrip
found 11 hours ago
Sat, Dec 5 - Tue, Dec 15
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$247 Roundtrip, found 4 hours ago
$247
Roundtrip
found 4 hours ago
Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$275 Roundtrip, found 3 hours ago
$275
Roundtrip
found 3 hours ago
Sat, Dec 5 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 3 days ago
$277
Roundtrip
found 3 days ago
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