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Welcome to Winchester! This destination is located in Eastern Massachusetts, an area popular for its attractive coastal plains, sandy beaches and bays.

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.

Top Hotel Deals

See all 827 Hotels in Winchester
Nice Room in Scenic Area

Nice Room in Scenic Area

200 Swanton St, Winchester
0.0 out of 5.0

Situated in Winchester, this apartment is within 9 mi (15 km) of Woburn Mall, USS Constitution Museum, and TD Garden. Faneuil Hall Marketplace and Burlington Mall are also within 9 mi (15 km).

Boston Park Plaza

Boston Park Plaza

50 Park Plaza at Arlington Street, Boston
of 5, from 528 reviews
4.0 out of 5.0

Located in historic Back Bay, this hotel just completed a $100 million dollar renovation, and is 3 miles from Logan International Airport and 200 yards from the Boston Common and Public Garden. The hotel is easily accessible to Newbury Street shopping.

Charles Street Inn

Charles Street Inn

94 Charles St, Boston
of 5, from 10 reviews
0.0 out of 5.0

Located in Beacon Hill, this bed & breakfast is within a 10-minute walk of Boston Public Garden, Boston Common, and Massachusetts General Hospital. Massachusetts State House and Orpheum Theater are also within 15 minutes.

Spacious 2BR in Downtown Boston by Sonder

Spacious 2BR in Downtown Boston by Sonder

Milk Street and Batterymarch st, Boston
3.5 out of 5.0

Located in Boston Financial District, this apartment is within a 5-minute walk of Faneuil Hall Marketplace and New England Aquarium. Boston City Hall and Orpheum Theater are also within 10 minutes.

Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree

50 Forbes Road, Braintree
of 5, from 555 reviews
3.5 out of 5.0

Hyatt Place Boston/Braintree is located right across the street from premier shopping at South Shore Plaza. Guests can take a free shuttle to select destinations within a 3-mile (4.8-km) radius, and downtown attractions like the New England Aquarium and Museum of Science are a 30-minute drive.

Bird's Eye View by Vacasa

Bird's Eye View by Vacasa

4 Longfellow Place, Boston
of 5, from 2 reviews
4.0 out of 5.0

Located in West End, this apartment is within a 10-minute walk of TD Garden and Massachusetts General Hospital. Faneuil Hall Marketplace and Massachusetts State House are also within 15 minutes.

Assembly Row Apartments by Next Star

Assembly Row Apartments by Next Star

21 Michigan Ave, Somerville
3.5 out of 5.0

Situated in Somerville, this apartment is 0.8 mi (1.4 km) from LEGOLAND® Discovery Center Boston and within 3 mi (5 km) of USS Constitution Museum and TD Garden. Harvard Square and Faneuil Hall Marketplace are also within 3 mi (5 km).

Hilton Boston Logan Airport

Hilton Boston Logan Airport

One Hotel Drive, Boston
of 5, from 1,428 reviews
4.0 out of 5.0

This hotel is connected to Logan Airport terminals by a climate-controlled skybridge. A complimentary 24-hour airport shuttle is also available.

Top Flight + Hotel Deals

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