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Chester Vacation Packages

Considering a Chester vacation? It's time to start organizing.

Save Time and Money with a Chester Package Deal

Expedia will help you save when you purchase a package. Combining your flight and hotel purchases is the easiest way you can save. Go shopping in Chester with the extra money.

Crafty jetsetters can save up to $583 by getting their package deals with us.

Our extensive global database not only provides 400 partner airlines and 321,000 worldwide hotels, but also features fantastic savings too.

See the great deals at Expedia and finalize that special trip you so badly deserve. You'll be surprised you didn't do it sooner.

You don't have to worry about postponing your family's travel plans, as we do not charge additional cancellation fees for almost all of our hotel bookings.

Chester Vacation Packages

From Chester, it is roughly 55 miles east to Concord and 70 miles north to Montpelier.

Make time for a Proctorsville side trip. This location is merely 9 miles to the north and has Okemo Mountain Ski Resort.

There is little else that restores the soul like a trip to the ocean. Pack a picnic, buy your favorite wine and bask in the lovely scenery of Million Dollar Beach, 55 miles west from Chester. Another wonderful place is Endicott Rock Park, 60 miles to the northeast.

Many travelers visit this part of Central Vermont- Killington for its beloved natural surroundings. Find out what it's all about at Chesterfield Gorge Natural Area and Madame Sherri Forest, 25 miles and 30 miles away from Chester, respectively.

Put on some warm socks and hit the trails at the resorts near Chester. Pats Peak and Ragged Mountain Ski Resort are 40 miles and 40 miles away, respectively.

Make sure you stop at Vermont Institute of Contemporary Arts or DaVallia Art & Accents.

Rutland Southern Vermont Regional Airport is the closest airport at about 25 miles to the northwest, so just make sure you leave plenty of time.

Accommodation in Chester

There are only a few hotels in Chester on the Expedia lodging page, so it's wise to book ahead.

Some of the lodgings that might tick your boxes in Chester are the Hugging Bear Inn and Shoppe and Rose Arbour Bed & Breakfast.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Top Hotel Deals

See all 369 Properties in Chester
The Karass Inn $109
The Karass Inn

The Karass Inn

225 Pleasant Street, Chester
     
    4.4
    of 5, from 29 reviews
    3.0 out of 5.0

    Situated in a state park, this bed & breakfast is within 9 mi (15 km) of Grafton Historical Society, Vermont Museum of Mining and Minerals, and Gallery North Star. The Nature Museum and Grafton Ponds Outdoor Center are also within 9 mi (15 km).

    Chester House Inn $139
    Chester House Inn

    Chester House Inn

    266 Main St, Chester
       
      4.3
      of 5, from 38 reviews
      3.0 out of 5.0

      Situated in Chester, this bed & breakfast is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

      Rose Arbour Bed & Breakfast $94
      Rose Arbour Bed & Breakfast

      Rose Arbour Bed & Breakfast

      55 School Street, Chester
         
        4.0
        of 5, from 66 reviews
        2.5 out of 5.0

        Situated in the historical district, this bed & breakfast is 0.2 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

        Fullerton Inn $114
        Fullerton Inn

        Fullerton Inn

        40 The Common, Chester
           
          3.8
          of 5, from 32 reviews
          2.5 out of 5.0

          Situated in Chester, this inn is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

          Inn Victoria $126
          Inn Victoria

          Inn Victoria

          321 Main St, Chester
             
            4.7
            of 5, from 31 reviews
            4.0 out of 5.0

            Situated in Chester, this bed & breakfast is 0.3 mi (0.5 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

            Hugging Bear Inn and Shoppe $119
            Hugging Bear Inn and Shoppe

            Hugging Bear Inn and Shoppe

            244 Main Street, Chester
               
              4.3
              of 5, from 55 reviews
              2.5 out of 5.0

              Situated in Chester, this bed & breakfast is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

              Motel in the Meadow $79
              Motel in the Meadow

              Motel in the Meadow

              936 VT Route 11 West, Chester
                 
                4.1
                of 5, from 32 reviews
                2.5 out of 5.0

                Situated in Chester, this motel is 1.7 mi (2.7 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

                1868 Quaint & Cozy Carriage House-20 min to Okemo
                1868 Quaint & Cozy Carriage House-20 min to Okemo

                1868 Quaint & Cozy Carriage House-20 min to Okemo

                , Chester
                   
                  5.0
                  of 5, from 2 reviews
                  0.0 out of 5.0

                  Situated in Chester, this historic guesthouse is 0.6 mi (0.9 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

                  Top Deals on Flights

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