Brookline Vacation Packages 2025

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Where to stay in Brookline

3 out of top 10 points of interest in this area

While you're in North Brookline, take in top sights like Coolidge Corner Theatre and jump on the metro at Coolidge Corner Station to see more of the city.

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Cleveland Circle is a destination travelers like for its restaurants, and you might hop aboard the metro at Cleveland Circle Station or Reservoir Station to explore sights like Chestnut Hill Reservation.

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Sometimes winter is terrifying after lots of #snow and ice #iciclesofdeath #architecture #Bestof5 #WinterWonders

Centered around Beacon and Harvard Streets, this Brookline neighborhood boasts a pedestrian-friendly atmosphere, diverse dining options like crêperies and falafel joints, and cultural gems such as the Art Deco Coolidge Corner Theatre. Easily accessible via the Green Line C branch and #66 bus route.

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Don’t tell the locals, but this is my secret FREE PARKING place for Fenway Park for their 7 pm games or Sunday all day. It’s 2 hour parking until 8 pm so technically you shouldn’t arrive earlier than 6:00
PM, but I arrived at 5:30 ish and nary a ticket officer to see. Saved $40-$50 on parking in an overcrowded lot and traded hassling with ticket vouchers and crowds for an enjoyable and easy and most important safe walk. You just have to be out by 2:00 am.

While you're strolling through Longwood, you may want to check out the coffeehouses and architecture. If you want to see more of the area, hop on the metro at Longwood Station or Hawes St. Station.

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Even though there aren't top sights in Corey Hill, you can explore the larger area and take in top sights like Fenway Park. Jump on the metro at Fairbanks St. Station to see more of the city.

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