Holidays in Portland

Holidays in Portland

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£163 - £239£239 - £315£315 - £391£391 - £467£467+ 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
£374
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
£172
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
£216
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
£182
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
£317
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
£213
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
£174
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
£305
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
£200
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
£183
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
£212
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
£183
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
£227
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
£270
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
£169
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
£214

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 £611; Family holiday £615; Romantic holiday £646; Luxury holiday £646; Budget holiday £526.

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)£611
Family holiday (Flight+Hotel)£615
Romantic holiday (Flight+Hotel)£646
Luxury holiday (Flight+Hotel)£646
Budget holiday (Flight+Hotel)£526