Vacations in Portland

Vacations in Portland

2 travelers

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Cheap Portland package deals

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$221 - $921$921 - $1,620$1,620 - $2,320$2,320 - $3,019$3,019+ per night

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Most popular Portland flight and hotel deals

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Canopy by Hilton Portland Waterfront - Portland - Lounge
Canopy by Hilton Portland Waterfront - Portland - Lounge
Canopy by Hilton Portland Waterfront
9.2 Wonderful
Free Wi-Fi
Pet friendly
Tulsa
Meals not included
3 nights + flight
$748
Ramada Plaza Portland - Portland - Lounge
Ramada Plaza Portland - Portland - Lounge
Ramada Plaza Portland
7.3 Good
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$291
Embassy Suites by Hilton Portland Maine - Portland - Restaurant
Embassy Suites by Hilton Portland Maine - Portland - Restaurant
Embassy Suites by Hilton Portland Maine
8.7 Very good
Airport shuttle
Free Wi-Fi
Pool
Pet friendly
Chicago Midway
Breakfast
3 nights + flight
$478
Courtyard by Marriott Portland Downtown/Waterfront - Portland - Lounge
Courtyard by Marriott Portland Downtown/Waterfront - Portland - Lounge
Courtyard by Marriott Portland Downtown/Waterfront
8.1 Very good
Airport shuttle
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$525
Aloft Portland, Me - Portland - Bar
Aloft Portland, Me - Portland - Bar
Aloft Portland, Me
8.3 Very good
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$479
Hyatt Place Portland Old Port - Portland - Restaurant
Hyatt Place Portland Old Port - Portland - Restaurant
Hyatt Place Portland Old Port
8.5 Very good
Airport shuttle
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$511
The Weldon Hotel - Portland - Bedroom
The Weldon Hotel - Portland - Bedroom
The Weldon Hotel
9.7 Wonderful
Free Wi-Fi
Pet friendly
Tulsa
Meals not included
3 nights + flight
$764
Ac Hotel Portland Downtown-Waterfront, Me - Portland - Bar
Ac Hotel Portland Downtown-Waterfront, Me - Portland - Bar
Ac Hotel Portland Downtown-Waterfront, Me
8.8 Very good
Airport shuttle
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$578
Hampton Inn & Suites Portland West - Portland - Bedroom
Hampton Inn & Suites Portland West - Portland - Bedroom
Hampton Inn & Suites Portland West
8.2 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
$454
Motel 6 Portland Me - Portland - Building
Motel 6 Portland Me - Portland - Building
Motel 6 Portland Me
5.2 Fair
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$221
Doubletree By Hilton Portland, Me - Portland - Pool
Doubletree By Hilton Portland, Me - Portland - Pool
Doubletree By Hilton Portland, Me
7.6 Good
Parking
Airport shuttle
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$328
Fireside Inn & Suites Portland - Portland - Bedroom
Fireside Inn & Suites Portland - Portland - Bedroom
Fireside Inn & Suites Portland
7.4 Good
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$324
Hilton Garden Inn Portland-Airport - Portland - Bar
Hilton Garden Inn Portland-Airport - Portland - Bar
Hilton Garden Inn Portland-Airport
7.9 Good
Airport shuttle
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$490
Portland Harbor Hotel - Portland - Patio
Portland Harbor Hotel - Portland - Patio
Portland Harbor Hotel
8.4 Very good
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$652
Hampton Inn Portland Downtown - Waterfront - Portland - Building
Hampton Inn Portland Downtown - Waterfront - Portland - Building
Hampton Inn Portland Downtown - Waterfront
8.4 Very good
Free Wi-Fi
Pool
Pet friendly
Tulsa
Breakfast
3 nights + flight
$572
Clarion Hotel Airport - Portland - Bedroom
Clarion Hotel Airport - Portland - Bedroom
Clarion Hotel Airport
7.4 Good
Parking
Airport shuttle
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$288

When to book a vacation in Portland

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

Tips for finding Portland package deals

  • There are loads of types of vacations 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 travelers: Top vacation $383; Family vacation $362; Romantic vacation $434; Luxury vacation $450; Budget vacation $265.

Where to stay in Portland

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

Everything you need to know for your vacation in Portland

Portland vacation information

Top vacation (Flight+Hotel)$383
Family vacation (Flight+Hotel)$362
Romantic vacation (Flight+Hotel)$434
Luxury vacation (Flight+Hotel)$450
Budget vacation (Flight+Hotel)$265

Portland vacation: Search Portland vacation packages on KAYAK. KAYAK is a travel tool that searches Portland trips on hundreds of travel sites to help you find the Portland package that suits you best. Discover Portland deals now and book your Portland flight and hotel today.

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