When To Go
The great thing about taking a city vacation is that no matter the weather – sweltering heat, snowstorm, or anything in between – you can bet the attractions you came to see are open for business. That said, months when it isn't too hot and isn't too cold are the best for comfortable exploring – in Boston, these months come in spring (April – June) and autumn (September – October). These are the high season, and you can expect to find hotels at their priciest, restaurants their most crowded, and lines longest. Summer is also a busy time, with families trying to educate the little ones at the Boston historical attractions on their summer vacations. The low season, January through March, is a great time to score rock-bottom rates on hotel rooms and highly coveted restaurant reservations. However, it's likely to be quite cold during your visit. You'll get the best bang for your buck if you visit in November and early December – the weather will probably be chilly but bearable and prices at hotels are less expensive and the crowds have disappeared for the winter.
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$49+: Fare Sale on Award-Winning Virgin America; Ends 3/22 Virgin America
$253+: Boston, MA from Alexandria, LA (round-trip) Major Airlines
$264+: Boston, MA from Amarillo, TX (round-trip) Major Airlines
$196+: Boston, MA from Appleton, WI (round-trip) Travelocity
$253+: Alexandria, LA to Boston, MA (round-trip) Travelocity
$264+: Amarillo, TX to Boston, MA (round-trip) Major Airlines
$196+: Boston, MA from Appleton, WI (round-trip) Travelocity
17-Nt Europe, United States, and Canada Cruise from $899 Editors' Review
$999+: Spring 7-Nt Cruise from Montreal to Boston on HAL Travelocity
$999+: 7-Nt New England Cruise from Montreal to Boston Travelocity
$431+: High-Rise Charles River Hotel w/Air & 3 Nights Expedia
$370+: 3-star Four Points By Sheraton Norwood Expedia
$116+: Wyndham Boston w/Airport Shuttle & Breakfast Expedia
$151+: Boston Inn Near the T Stop w/WiFi & Satellite TV Expedia
$154+: Boston Hotel Near Fenway Park w/WiFi & Breakfast Boston Hotel Buckminster
$58+: Special Rates on Premium 3.5-Star Hotels in Boston Hotwire.com
$179/nt+: 4-star Hilton Boston Logan Airport Expedia
$299/nt+: 4-star The Westin Copley Place Expedia
$169/nt+: 3-star The Boston Park Plaza Hotel & Towers Expedia