Portland, Maine Deals from $118: Round-Trip Flights, the Historic Old Port & Casco Bay

Maine’s largest city mixes cobblestone streets, red-brick warehouses and a working harbor with a food scene that ranges from fresh seafood to the Whoopie Pie. Just south of town, Portland Head Light watches over Casco Bay.

TravelDeals24 currently lists three Portland offers: round-trip flights from $118, a 2-night Old Port break from $125 per person and three nights downtown by the waterfront with breakfast from $191 per person. Hotel prices are per person based on two people traveling together.

$118 – Portland, Maine: Great Value Return Flights

Round-trip flights to Portland start at $118. The deal page lists sample round-trip prices such as Orlando and Tampa from $152, New York City from $205 and Norfolk, VA from $255; more departure airports are available.

• Round-trip flights to Portland, Maine
• From $118; sample prices: Orlando and Tampa from $152, NYC from $205, Norfolk from $255
• Limited dates: the prices apply to sample dates; more departure airports available

View the Portland flight deal at TravelDeals24 »

$125 – Portland, Maine: 3 Days Utterly Charming Historic Old Port Break

Two nights in the historic Old Port at the Portland Regency Hotel & Spa, an elegant historic building just moments from the water. Guests praise its central location, friendly service and comfortable rooms; the harbor, seafood restaurants, craft breweries and the Portland Museum of Art are all close by.

• 3* Portland Regency Hotel and Spa, Old Port, Portland, Maine
• Very good 4.2/5 Tripadvisor traveler rating with Travelers’ Choice Award, free cancellation option
• 2 nights room only, spa, restaurant and bar, free Wi-Fi and free airport transportation; from $125 per person ($250 for two)

View the Old Port break at TravelDeals24 »

$191 – Portland, ME: 4 Days Exciting Casco Bay & Downtown Stay with Breakfast

Three nights downtown with breakfast at the Residence Inn by Marriott Portland Downtown Waterfront, close to Casco Bay and the Old Port. There is a heated pool and an outdoor fireplace, kids stay free and pets are welcome.

• 3* Residence Inn by Marriott Portland Downtown Waterfront, Portland, Maine
• Good 4.2/5 Tripadvisor traveler rating, free cancellation option
• 3 nights with breakfast, heated pool, kitchenette, kids stay free; from $191 per person ($382 for two)
• Price drop: previously advertised at $212, now from $191 per person, that is $21 less

View the Casco Bay stay with breakfast at TravelDeals24 »

Prices were checked on the TravelDeals24 deal pages in October 2026 and apply to sample dates; prices may vary.

Prices are per person based on two people traveling together. Offers are provided by TravelDeals24 and are subject to availability; prices may change.