19 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Cruise.com

Sail roundtrip from New York City to Boston, Portland, Saint John & Halifax.

Depart Sept. 6 & 20, 2015
 
Source: Kiva Tea Bar & Spa

Kiva Tea Bar & Spa offers "ultimate pampering and relaxation" (USA Today). For more than $50 off, indulge in a two-service spa package with lunch.

Sept. 19, 2014 - Jan. 16, 2015
 
Source: WineUp On Williams

WineUp On Williams owner, Wayne Oppenheimer, is "keeping Portland weird one wine drinker at a time" (Examiner.com). Save 55% on wine and bites for two.

Sept. 16, 2014 - Dec. 16, 2014
 
Source: ME SPA

Subscribers can save over 55% on a range of massages and facials at seven ME SPA locations nationwide, great for a private winter escape or a relaxing gift.

Through Feb. 28, 2015
 
Source: Hotel Rose

Many of the city's most popular attractions are within walking distance

Through February
 
Source: Hotel Modera

This stylish hotel has earned praise from Conde Nast Traveler and embraces Portland's creative side.

Through January
 
Source: Mark Spencer Hotel

The Pearl District is "Portland's hip urban loft scene" and home to upscale restaurants (Frommer's).

December-February; +$20 weekends
 
Source: Jupiter Hotel

Explore the trendy neighborhoods, restaurants and music venues of Portland with a winter hotel deal.

Sundays-Thursdays December-March; +$20 weekends
 
Source: Portland Marriott Downtown Waterfront

Explore downtown Portland from this centrally located riverside hotel.

Thursdays-Sundays, Nov. 27, 2014 - March 21, 2015
 
Source: Heathman Hotel

This 4-star hotel is ideally located for exploring Portland.

Dec. 2, 2014 - March 31, 2015
 
Source: Best Western Inn at the Meadows

Stay any day of the week at a hotel just 7 miles from downtown Portland.

Dec. 1 - Feb. 8
 
Source: La Quinta Inn & Suites Portland Airport

Spend time in Portland this winter, and take advantage of hotel savings.

Through February; +$17 March-May
 
Source: Sheraton Portland Airport Hotel

Visit Portland with this hotel deal valid over weekends and including free parking.

Through January
 
Dec. 2-23; Depart onTues., Wed., Sat.
Alaska Airlines
 
 
 
 
 
 
Cheap Roundtrip Fares to Portland from:
(Per person, including taxes and fees. Click a price to verify availability now.)
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Travelzoo Tips

Hilary Solan — Travel, Entertainment and Local Deal Expert
Hilary Solan
Deal Expert, Chicago
Several hotel chains, including Hilton and Choice Hotels, offer discounts for active More