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Windsor

Even though Windsor might be outclassed by vacation behemoths like Rio de Janeiro or Sydney, you'll find this The Berkshires destination is still worth checking out.

Windsor Vacation Packages

Windsor is located approximately 35 miles away from Albany and 55 miles from Hartford.

Relax by the ocean, stretch your legs and dip your feet in the water at Crystal Lake Sandy Beach, 55 miles southeast of Windsor.

Adventurous types will relish in the stunning environmental reserves of The Berkshires. Amethyst Conservation Area is located 30 miles away from Windsor, while Great Falls Discovery Center lies 25 miles away.

Take in some sports at Mullins Center, where the UMass Minutemen and UMass Minutemen can be seen. Relive the match's highlights over a few drinks with local sports fanatics after the game in one of the nearby watering holes.

Feel the fresh snow beneath your boots at Wachusett Mountain Ski Area or Mount Snow, 60 miles and 30 miles from the middle of town.

Savoy, 6 miles to the north, is a worthwhile locality. Make a stop and visit Hail to the Sunrise Statue and Tannery Falls. Cheshire, yet another worthwhile place, features Mount Greylock and Susan B. Anthony Birthplace Museum. This destination is 6 miles away.

Consider making the trip to Adams, a regional hub just 9 miles to the northwest of Windsor. This area boasts a variety of attractions, such as Mass MoCA, Natural Bridge State Park and Windsor Lake Park. Don't hit the road until you've also experienced Studio 21 South and North Adams Public Library.

Take your taste buds on an exciting adventure through the culinary traditions of The Berkshires.

A delectable meal relies upon the quality of its ingredients. Luckily for us, the cod and clams here are fantastic.

Do you have a bit of a sweet tooth? Treat yourself to some frappe

You should be pleased to learn that the 4th of July is Independence Day, a festive day for the whole country.

If you're looking for Windsor's closest airport, it is approximately 40 miles away.


Top Hotel Deals

See all 121 Hotels in Windsor
£97
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock
4.2
of 5, from 769 reviews
0.0 out of 5.0

Situated in Hancock, this condo is 5.8 mi (9.3 km) from Mount Greylock State Reservation Visitor Center and within 12 miles (20 km) of Waubeeka Golf Links and New Lebanon Library. Mount Lebanon Shaker Village and Berkshire Athenaeum are also within 12 miles (20 km).

£94
Cranwell Spa and Golf Resort

Cranwell Spa and Golf Resort

55 Lee Road, Lenox
4.1
of 5, from 97 reviews
4.0 out of 5.0

Situated in Lenox, this spa resort is within 2 miles (3 km) of The Mount, Ventfort Hall Mansion and Gilded Age Museum and Lenox Library. Shakespeare and Company and Wood's Pond are also within 3 miles (5 km).

£67
Crowne Plaza Pittsfield-Berkshires

Crowne Plaza Pittsfield-Berkshires

1 West St, Pittsfield
3.6
of 5, from 442 reviews
4.0 out of 5.0

Located in the heart of Pittsfield, this hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater and Berkshire Athenaeum. Canoe Meadows Wildlife Sanctuary and Arrowhead Museum are also within 3 miles (5 km).

£73
Holiday Inn Berkshires

Holiday Inn Berkshires

40 Main St, North Adams
4.1
of 5, from 441 reviews
3.5 out of 5.0

Located in the heart of North Adams, this hotel is within a 10-minute walk of Mass MoCA, North Adams Public Library and Western Gateway Heritage State Park. Windsor Lake Park and Natural Bridge State Park are also within 2 miles (3 km).

£82
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd, Lenox
4.6
of 5, from 33 reviews
3.5 out of 5.0

Situated in Lenox, this hotel is within 2 miles (3 km) of Kennedy Park, Lenox Library and Pleasant Valley Wilderness Sanctuary. Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company are also within 3 miles (5 km).

£76
Hampton Inn & Suites Berkshires Lenox

Hampton Inn & Suites Berkshires Lenox

445 Pittsfield Rd, Lenox
4.6
of 5, from 346 reviews
2.5 out of 5.0

Situated in a rural location, this hotel is within 2 miles (3 km) of Arrowhead Museum, Kennedy Park and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary and Canoe Meadows Wildlife Sanctuary are also within 3 miles (5 km).

£81
Hilton Garden Inn Lenox/Pittsfield

Hilton Garden Inn Lenox/Pittsfield

1032 South Street, Pittsfield
4.7
of 5, from 84 reviews
3.5 out of 5.0

Situated in Pittsfield, this hotel is 1.2 mi (1.9 km) from Bousquet Ski Area and within 3 miles (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and Berkshire Museum are also within 3 miles (5 km).

£56
Black Swan Inn, an Ascend Collection Hotel

Black Swan Inn, an Ascend Collection Hotel

435 Laurel St, Lee
4.1
of 5, from 354 reviews
3.5 out of 5.0

Situated on a lake, this hotel is within 1 mile (2 km) of Animagic Museum of Animation and Lee Library. Greenock Country Club and The Mount are also within 3 miles (5 km).

Top Deals on Flights

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