10 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: Portland Prime

For 50% off, sit down to a steak dinner with wine for two at Portland Prime, which boasts an OpenTable Diners' Choice award for Special Occasion dining.

July 21, 2014 - Nov. 30, 2014
 
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
 
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