Winchester Vacation Deals

Packages in Winchester

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Winchester Vacation Packages

Winchester is just 8 miles northwest of the city of Boston.

If you want to discover more of the region, a day trip to Wollaston Beach is a recommended option. It's just 14 miles southeast from Winchester. Some of the leading attractions here include Boston Common and Boston Public Garden.

Melrose has a couple of decent tourist hotspots. It's only 4 miles east of Winchester. Old North Church and Copp's Hill Burying Ground are among the best options. Also stop by Bunker Hill Monument.

Grab a book and a picnic blanket and relax by the seaside. Plymouth Long Beach, 45 miles to the southeast, and Oakland Beach, 55 miles to the south, are well worth your time.

Adventurous types pass through this region to admire its marvelous natural areas. Discover what it's all about at Minuteman Bikeway and Natural Resources Trust of Easton, 8 miles and 25 miles away from Winchester, respectively.

Fortunately, there are some beautiful areas that are easy to get to. Just two recommended ones are Whip Hill and Prospect Hill Park.

Take in some live sports at Gillette Stadium in Foxboro, 25 miles to the south of Winchester. Support the UMass Minutemen, New England Patriots or New England Revolution. Put on something with maroon and white, the colors of the UMass Minutemen, and get ready for some awesome college football.

For a winter getaway, you can't go wrong with Blue Hills Ski Area, 17 miles away from Winchester, or Nashoba Valley Ski Area, 16 miles away.

Don't miss out on Winter Pond. Also try out Horn Pond.

When it's time for your flight home, make your way to the nearest airport, 9 miles to the southeast.

Winchester provides hotel and other short-stay apartment options for all types of vacationers. Using the Expedia booking guide, visitors can choose from 6 Winchester hotels and motels.

Two of the more luxurious Winchester hotels are The Charles Hotel, at One Bennett Street, and the Kimpton Onyx Hotel, at 155 Portland St. Alternatively, The Harvard Square Hotel, at 110 Mount Auburn Street, and the Days Hotel-Boston/Cambridge, at 1234 Soldiers Field Rd, are some offerings that might be preferable if you're traveling on the cheap.