Holidays in Portland

Holidays in Portland

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£164 - £240£240 - £316£316 - £393£393 - £470£470+ per night

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Most popular Portland flight and hotel deals

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Fleetwood House Bed & Breakfast - Portland - Balcony
Fleetwood House Bed & Breakfast - Portland - Balcony
Fleetwood House Bed & Breakfast
8.4 Very Good
Free Wi-Fi
Pet-friendly
Air conditioning
Chicago O'Hare Intl
Meals not included
3 nights + flight
£376
Ramada Plaza Portland - Portland - Lounge
Ramada Plaza Portland - Portland - Lounge
Ramada Plaza Portland
7.4 Good
Parking
Free Wi-Fi
Pool
Pet-friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
£173
Hilton Garden Inn Portland Downtown Waterfront - Portland - Lounge
Hilton Garden Inn Portland Downtown Waterfront - Portland - Lounge
Hilton Garden Inn Portland Downtown Waterfront
8.7 Very Good
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Chicago O'Hare Intl
Meals not included
3 nights + flight
£217
Aloft Portland, Me - Portland - Bar
Aloft Portland, Me - Portland - Bar
Aloft Portland, Me
8.4 Very Good
Free Wi-Fi
Pet-friendly
Air conditioning
Chicago O'Hare Intl
Meals not included
3 nights + flight
£183
The Weldon Hotel - Portland - Bedroom
The Weldon Hotel - Portland - Bedroom
The Weldon Hotel
9.4 Wonderful
Free Wi-Fi
Pet-friendly
Air conditioning
Chicago O'Hare Intl
Meals not included
3 nights + flight
£319
AC Hotels by Marriott Portland Downtown/Waterfront, ME - Portland - Bar
AC Hotels by Marriott Portland Downtown/Waterfront, ME - Portland - Bar
AC Hotels by Marriott Portland Downtown/Waterfront, ME
8.8 Very Good
Airport shuttle
Free Wi-Fi
Pet-friendly
Air conditioning
Chicago O'Hare Intl
Meals not included
3 nights + flight
£215
Holiday Inn Portland-By The Bay - Portland - Lounge
Holiday Inn Portland-By The Bay - Portland - Lounge
Holiday Inn Portland-By The Bay
8.4 Very Good
Airport shuttle
Free Wi-Fi
Pool
Air conditioning
Chicago O'Hare Intl
Meals not included
3 nights + flight
£175
Blind Tiger Portland - Danforth Street - Portland - Bedroom
Blind Tiger Portland - Danforth Street - Portland - Bedroom
Blind Tiger Portland - Danforth Street
8.8 Very Good
Free Wi-Fi
Air conditioning
Chicago O'Hare Intl
Breakfast
3 nights + flight
£307
Fireside Inn & Suites Portland - Portland - Patio
Fireside Inn & Suites Portland - Portland - Patio
Fireside Inn & Suites Portland
7.4 Good
Parking
Free Wi-Fi
Pool
Pet-friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
£201
The Westin Portland Harborview - Portland - Bar
The Westin Portland Harborview - Portland - Bar
The Westin Portland Harborview
8.3 Very Good
Free Wi-Fi
Pet-friendly
Air conditioning
Chicago O'Hare Intl
Meals not included
3 nights + flight
£184
Hilton Garden Inn Portland-Airport - Portland - Bar
Hilton Garden Inn Portland-Airport - Portland - Bar
Hilton Garden Inn Portland-Airport
8.1 Very Good
Airport shuttle
Free Wi-Fi
Pool
Pet-friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
£213
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med - Portland - Bedroom
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med - Portland - Bedroom
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
7.8 Good
Airport shuttle
Free Wi-Fi
Pool
Pet-friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
£184
Portland Harbor Hotel - Portland - Patio
Portland Harbor Hotel - Portland - Patio
Portland Harbor Hotel
8.5 Very Good
Free Wi-Fi
Pet-friendly
Air conditioning
Chicago O'Hare Intl
Meals not included
3 nights + flight
£229
The Francis - Portland - Building
The Francis - Portland - Building
The Francis
9 Wonderful
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Chicago O'Hare Intl
Meals not included
3 nights + flight
£271
Clarion Hotel Portland Airport Me - Portland - Bedroom
Clarion Hotel Portland Airport Me - Portland - Bedroom
Clarion Hotel Portland Airport Me
7.4 Good
Parking
Airport shuttle
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
£170
Residence Inn by Marriott Portland Downtown/Waterfront - Portland - Lobby
Residence Inn by Marriott Portland Downtown/Waterfront - Portland - Lobby
Residence Inn by Marriott Portland Downtown/Waterfront
8.6 Very Good
Airport shuttle
Free Wi-Fi
Pool
Pet-friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
£215

When to book a holiday in Portland

Price includes flights and 3 nights accommodation for 2 travellers. Prices are not fixed and may vary with time.

Tips for finding cheap holiday packages Portland

  • There are loads of types of holidays in Portland and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travellers: Top holiday £615; Family holiday £618; Romantic holiday £650; Luxury holiday £650; Budget holiday £529.

Where to stay in Portland

Our map will help you find the perfect place to stay for your holiday in Portland by showing you the exact location of each hotel.

Everything you need to know for your holiday in Portland

Portland holiday information

Top holiday (Flight+Hotel)£615
Family holiday (Flight+Hotel)£618
Romantic holiday (Flight+Hotel)£650
Luxury holiday (Flight+Hotel)£650
Budget holiday (Flight+Hotel)£529