37 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 and Halifax. Take in early fall colors along the coast.

Depart Sept. 6, 20
 
Source: Sheraton Boston

Explore the historic Back Bay neighborhood of Boston this winter while saving big when compared to surrounding dates.

Select dates through March
 
Source: DoubleTree Suites by Hilton Boston - Cambridge

Visit Cambridge, the home of Harvard, this winter for 27% off while staying in a spacious one-bedroom suite.

Through Feb. 25
 
Source: The Westin Boston Waterfront

Enjoy savings at this hotel with views of the Boston Harbor and a short walk from the historic sights of downtown.

Select dates through March
 
Source: Taza Chocolate

Visit the Taza Chocolate factory for an experience that landed a spot on Boston Magazine's 2014 Best of Boston list. Save more than 45% on tours.

Tuesday-Sunday through Feb. 12, 2015
 
Source: Cheers

Dine for half off at the famous bar that inspired the Emmy Award-winning TV show "Cheers"; one Travelzoo member called it an "all around good time."

Through Feb. 28, 2015
 
Source: Savvor Restaurant & Lounge

Savvor Restaurant & Lounge serves "sassy southern specialties" (The Boston Globe). Dine for half off at the Leather District spot.

Tuesday-Saturday through March 1, 2015
 
Source: The Dining Room at The Living Room

"A restaurant inside a restaurant," The Dining Room at The Living Room lounge serves "eclectic" and "elegant fare" (The Boston Globe). Save more than 45%.

Sunday-Friday through March 5, 2015
 
Source: Serenity in the City Salon & Spa

Serenity in the City Salon & Spa earns an impressive 4.5 stars from Yelp users. Save up to 45% on spa packages.

Through March 8, 2015
 
Source: Aragosta Bar and Bistro

Sit down at the chef's counter for a Zagat-recommended dinner with wine pairings for less than $50 a person.

Through May 31, 2015
 
Source: Zocalo Back Bay

Save more than 40% at Zocalo Back Bay -- a "standby" bistro that serves "wonderful regional Mexican fare" that Zagat rates "very good to excellent" (24).

Through May 11, 2015
 
Source: Precinct Kitchen + Bar

Located in the former Boston Police headquarters, Precinct Kitchen + Bar exudes a "speakeasy-style" vibe and "American fare with newfangled twists" (Zagat).

Through March 18, 2015
 
Source: Parla

Serving "Italian food with an edge" (The Boston Globe), Parla was one of Zagat's 25 New Restaurants to Try in Boston in 2014.

Through Feb. 12, 2015
 
Source: Harvard Gardens

Harvard Gardens is "big with the locals" for "American fare done right" (Zagat). Save up to 50% at the Beacon Hill "neighborhood favorite" (Boston magazine).

Through Feb. 28, 2015
 
Source: Petit Robert Central

For an "utterly French experience," visit Petit Robert Central, which serves bistro fare that earns a "very good to excellent" rating (23) from Zagat.

Monday-Friday from 2-4 p.m. through March 30, 2015
 
Source: Nix's Mate

One of Boston.com's best new restaurants in 2013, Nix's Mate is an "unusually pretty restaurant" full of "creativity." Save 50% on dinner.

Through Jan. 31, 2015
 
Source: Bully Boy Distillers

Bully Boy Distillers, Boston's first craft distillery, earns a 4-star rating from Yelp users for its small-batch organic handcrafted spirits. Save 50% on tours.

Through June 30, 2015
 
Source: Boston Rock Gym

Save more than 55% at Boston Rock Gym -- one of the Best Indoor Rock Climbing Facilities in the area (CBS Boston).

Through May 7, 2015
 
Source: The Battery Lounge at Battery Wharf Hotel

Unwind with live jazz at the Battery Wharf Hotel's "dazzling" waterfront lounge (Fodor's) and save 45% on wine flights and cheese.

Friday-Saturday through April 4, 2015
 
Source: Gem Italian Kitchen, Nightclub & Lounge

Dine for half off brunch or dinner at Gem Italian Kitchen, which 91% of Travelzoo members praise for the "outstanding" food and "fantastic" service.

Wednesday-Sunday through March 25, 2015
 
Cheap Roundtrip Fares to Boston from:
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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