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Windsor Vacation Packages

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.

Packages in Windsor

Expedia has lodging and flight packages available for you. If you would like to save some extra money, consider how easy it is to combine your lodging and flight bookings with us. Experience more while in Windsor with the extra money.

If you book a package deal, you can save up to 17%.

With our worldwide database of around 400 partner airlines and 321,000 hotels, how can you ever go wrong?

Think of how much money you'll save with some of the best prices and packages via Expedia.

If you have to change your travel plans we can honor your cancellation request with no hidden fees, on almost all bookings.

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 134 Hotels in Windsor
Hilton Garden Inn Lenox Pittsfield £90
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

1032 South Street, Pittsfield
     
    4.7
    of 5, from 117 reviews
    3.0 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).

    Crowne Plaza Pittsfield-Berkshires £65
    Crowne Plaza Pittsfield-Berkshires

    Crowne Plaza Pittsfield-Berkshires

    1 West St, Pittsfield
       
      3.6
      of 5, from 483 reviews
      3.5 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).

      The Red Lion Inn £126
      The Red Lion Inn

      The Red Lion Inn

      30 Main Street, Stockbridge
         
        4.3
        of 5, from 176 reviews
        3.5 out of 5.0

        This family-friendly Stockbridge hotel is located in the historical district, within a 15-minute walk of Mission House, Berkshire Theatre Festival and Naumkeag. Berkshire Botanical Garden and National Shrine of the Divine Mercy are also within 3 miles (5 km).

        The Orchards Hotel £123
        The Orchards Hotel

        The Orchards Hotel

        222 Adams Rd, Williamstown
           
          4.4
          of 5, from 301 reviews
          3.5 out of 5.0

          Situated in a rural location, this hotel is within 1 mile (2 km) of Hopkins Observatory, Williams College Museum of Art and Chapin Library of Rare Books and Manuscripts. Williams College and 62 Center for Theater and Dance are also within 1 mile (2 km).

          Yankee Inn £59
          Yankee Inn

          Yankee Inn

          461 Pittsfield Rd, Lenox
             
            3.9
            of 5, from 518 reviews
            2.5 out of 5.0

            Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 miles (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. Lenox Library and Bousquet Ski Area are also within 3 miles (5 km).

            Berkshire Hills Country Inn £58
            Berkshire Hills Country Inn

            Berkshire Hills Country Inn

            1146 Cold Spring Road, Williamstown
               
              4.2
              of 5, from 92 reviews
              2.5 out of 5.0

              Situated in Williamstown, this hotel is within 3 miles (5 km) of Williamstown Historical Museum, Waubeeka Golf Links and 62 Center for Theater and Dance. Chapin Library of Rare Books and Manuscripts and Williams College Museum of Art are also within 3 miles (5 km).

              Holiday Inn Berkshires £83
              Holiday Inn Berkshires

              Holiday Inn Berkshires

              40 Main St, North Adams
                 
                4.1
                of 5, from 467 reviews
                3.0 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).

                Vacation Village in the Berkshires £94
                Vacation Village in the Berkshires

                Vacation Village in the Berkshires

                276 Brodie Mountain Rd, Hancock
                   
                  4.2
                  of 5, from 812 reviews
                  3.0 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).

                  Top Flight + Hotel Deals

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                  These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.