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Chester Vacation Packages

Newburgh boasts a population of around 29,000 permanent residents. If you base your trip in Chester, you'll no doubt meet quite a few of them! If you're arriving at Stewart International Airport, Chester lies 14 miles to the southwest. Alternatively, it's 16 miles to the southwest of the city's heart.

Save Time and Money with a Chester Package Deal

Expedia hotel and flight deals help you save! We would like to reduce your stress by pairing up your hotel and flight bookings for added savings. Go shopping in Chester with the extra money.

Book now and save up to C$590!

You don't need to click around a whole bunch of websites for your accommodations. With approximately 400 partner airlines and 321,000 hotels worldwide our thorough database has what you are looking for.

Your Newburgh vacation will seem that much sweeter with Expedia's prices.

Almost all hotel reservations can be changed with no extra charge from us.

Chester Vacation Packages

When you're settled in, it's time to go to some close tourist attractions. First off, try The Golf Club at Mansion Ridge or Museum Village. Make sure you don't forget about Harness Racing Museum & Hall of Fame and Goshen Historic Track. To experience a different side of Newburgh, make your way to the nearby neighborhoods Sugar Loaf and Monroe.

Accommodation in Chester

You won't find a wide range of hotel deals in Chester, so be sure to explore the listings and deals on Expedia's hotels page.

The following Chester accommodation options are worth checking out, the Holiday Inn Express Hotel & Suites Chester and Comfort Inn & Suites Goshen - Middletown

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.ca 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.


Top Hotel Deals

See all 243 properties in Chester
Holiday Inn Express Hotel & Suites Chester C$113
Holiday Inn Express Hotel & Suites Chester

Holiday Inn Express Hotel & Suites Chester

2 Bryle Place, Chester, NY
     
    4.0
    of 5, from 742 reviews
    2.5 out of 5.0

    Situated in the business district, this hotel is 0.4 mi (0.7 km) from Castle Fun Center and 1.4 mi (2.3 km) from The Rock Sports Complex. Woodbury Common Premium Outlets and United States Military Academy are also within 25 mi (40 km).

    The Dominion House Bed & Breakfast C$198
    The Dominion House Bed & Breakfast

    The Dominion House Bed & Breakfast

    50 Old Dominion Road, Chester, NY
       
      4.8
      of 5, from 18 reviews
      3.5 out of 5.0

      Situated in the mountains, this bed & breakfast is 3 mi (4.9 km) from Brotherhood Winery and within 9 mi (15 km) of Museum Village and Castle Fun Center. Museum Village and The Rock Sports Complex are also within 9 mi (15 km).

      Luxury NEW Sugar Loaf Apt Near Wineries/breweries C$231
      Luxury NEW Sugar Loaf Apt Near Wineries/breweries

      Luxury NEW Sugar Loaf Apt Near Wineries/breweries

      Chester, NY
         
        5.0
        of 5, from 6 reviews
        0.0 out of 5.0

        Situated in Chester, this romantic property is 2.5 mi (4 km) from The Rock Sports Complex and within 6 mi (10 km) of Museum Village and Castle Fun Center. Strazza Art Gallery and Museum Village are also within 9 mi (15 km).

        Mountain Creek C$180
        Mountain Creek

        Mountain Creek

        200 Route 94, Vernon, NJ
           
          4.0
          of 5, from 73 reviews
          3.0 out of 5.0

          Offering ski-in/ski-out access, this hotel in Vernon is next to a golf course, within a 5-minute walk of Mountain Creek Ski Resort and Mountain Creek Waterpark, and close to winter activities such as snow tubing. Granite Peak Quad and Hidden Valley Ski Resort are also within 3 mi (5 km).

          Super 8 by Wyndham Mahwah C$77
          Super 8 by Wyndham Mahwah

          Super 8 by Wyndham Mahwah

          160 State Route 17 South, Mahwah, NJ
             
            3.7
            of 5, from 760 reviews
            2.0 out of 5.0

            Situated in Mahwah, this hotel is 1.8 mi (2.8 km) from Ramapo College of New Jersey and within 9 mi (15 km) of Campgaw Mountain Ski Area and New York Country Club. Ringwood State Park and Harriman State Park are also within 12 mi (20 km). Mahwah Station is 18 minutes by foot.

            Super 8 by Wyndham Middletown C$86
            Super 8 by Wyndham Middletown

            Super 8 by Wyndham Middletown

            563 Route 211 E, I-84 Exit 4W Rt 17 Exit 120, Middletown, NY
               
              3.1
              of 5, from 808 reviews
              2.0 out of 5.0

              Situated in Middletown, this motel is within 3 mi (5 km) of Orange County Fairgrounds, Orange County Fair Speedway, and Paramount Theatre. Soons Orchards and Goshen Historic Track are also within 9 mi (15 km).

              Sleep Inn & Suites Middletown - Goshen C$104
              Sleep Inn & Suites Middletown - Goshen

              Sleep Inn & Suites Middletown - Goshen

              3491 Route 6, Middletown, NY
                 
                4.6
                of 5, from 329 reviews
                2.5 out of 5.0

                Located in the heart of Middletown, this hotel is 1.9 mi (3.1 km) from Paramount Theatre and 1.9 mi (3.1 km) from Soons Orchards. Orange County Fair Speedway and Orange County Fairgrounds are also within 6 mi (10 km).

                Grand Cascades Lodge C$326
                Grand Cascades Lodge

                Grand Cascades Lodge

                3 Wild Turkey Way, Hamburg, NJ
                   
                  4.1
                  of 5, from 134 reviews
                  4.0 out of 5.0

                  Conveniently located near the ski slopes, this Hamburg resort is within 6 mi (10 km) of Granite Peak Quad, Mountain Creek Ski Resort, and Mountain Creek Waterpark. Franklin Mineral Museum and Hidden Valley Ski Resort are also within 6 mi (10 km).