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Chester Vacations

Pack those stellar shades. We have Chester vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Chester – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Chester vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Chester

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Chester vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Chester well.

Top Hotel Deals

See all 113 Hotels in Chester
Mohegan Sun

Mohegan Sun

1 Mohegan Sun Boulevard, Montville
    4.5 out of 5.0
     
     

    Located in the heart of scenic Connecticut, between Boston, New York City, Providence, and Hartford, Mohegan Sun is a 15-minute drive from the wineries, golf ...

    Mohegan Sun$179

    Mohegan Sun$179
    Red Roof Inn Mystic - New London

    Red Roof Inn Mystic - New London

    707 Colman Street, New London
      2.0 out of 5.0
       
       

      Situated near the airport, this motel is 0.9 mi (1.4 km) from Lyman Allyn Art Museum and 1.3 mi (2.1 km) from United States Coast Guard Academy. Old Town Mill ...

      Red Roof Inn Mystic - New London$54

      Red Roof Inn Mystic - New London$54
      Hyatt Place Mohegan Sun

      Hyatt Place Mohegan Sun

      2049 Norwich, Montville
        3.0 out of 5.0
         
         

        Located in quiet Uncasville, just off highway CT-2A, Hyatt Place Mohegan Sun is a 7-minute drive from Mohegan Sun Casino. Guests can reach the Slater Memorial ...

        Hyatt Place Mohegan Sun$102

        Hyatt Place Mohegan Sun$102
        Holiday Inn New London - Mystic Area

        Holiday Inn New London - Mystic Area

        35 Governor Winthrop Blvd, New London
          3.5 out of 5.0
           
           

          This downtown New London hotel is 2 blocks from the Long Island and Block Island ferries. Mystic Aquarium, Mystic Seaport, U.S. Naval Sub Base, Ocean Beach Park, ...

          Holiday Inn New London - Mystic Area$123

          Holiday Inn New London - Mystic Area$123
          Hawthorn Suites by Wyndham Hartford Meriden

          Hawthorn Suites by Wyndham Hartford Meriden

          1151 E Main St, Meriden
            3.0 out of 5.0
             
             

            Situated in the business district, this hotel is within 1 mi (2 km) of Saint Johns Field, Black Pond State Wildlife Area, and Connecticut Law Enforcement Memorial. ...

            Hawthorn Suites by Wyndham Hartford Meriden$81

            Hawthorn Suites by Wyndham Hartford Meriden$81
            Baymont by Wyndham Branford/New Haven

            Baymont by Wyndham Branford/New Haven

            3 Business Park Dr, Branford
              2.0 out of 5.0
               
               

              This family-friendly Branford hotel is located near the airport, 4.1 mi (6.6 km) from Bishops Orchard and Winery, and within 12 mi (20 km) of Shoreline Trolley ...

              Baymont by Wyndham Branford/New Haven$85

              Baymont by Wyndham Branford/New Haven$85
              Microtel Inn & Suites by Wyndham Uncasville

              Microtel Inn & Suites by Wyndham Uncasville

              1954 Norwich New London Tpke, Montville
                2.5 out of 5.0
                 
                 

                Situated in Montville, this hotel is within 2 mi (3 km) of Mohegan Sun Casino, Mohegan Sun Arena, and Norwich Golf Course. Stoddard Hill State Park and Norwich ...

                Microtel Inn & Suites by Wyndham Uncasville$81

                Microtel Inn & Suites by Wyndham Uncasville$81
                Fairfield Inn & Suites by Marriott Uncasville

                Fairfield Inn & Suites by Marriott Uncasville

                2255 Norwich-New London Turnpike, Montville
                  3.0 out of 5.0
                   
                   

                  Situated in Montville, this hotel is within 1 mi (2 km) of Mohegan Sun Casino and Mohegan Sun Arena. Mystic Aquarium and Institute for Exploration and Mystic ...

                  Fairfield Inn & Suites by Marriott Uncasville$85

                  Fairfield Inn & Suites by Marriott Uncasville$85
                  Super 8 by Wyndham Cromwell/Middletown

                  Super 8 by Wyndham Cromwell/Middletown

                  1 Industrial Park Road, Cromwell
                    2.0 out of 5.0
                     
                     

                    Situated in Cromwell, this hotel is 1.4 mi (2.3 km) from Wilcox Park and within 6 mi (10 km) of Smith Park and Safari Golf. Dinosaur State Park and New Britain ...

                    Super 8 by Wyndham Cromwell/Middletown$51

                    Super 8 by Wyndham Cromwell/Middletown$51
                    Best Western Plus North Haven Hotel

                    Best Western Plus North Haven Hotel

                    201 Washington Avenue, North Haven
                      3.0 out of 5.0
                       
                       

                      Situated in North Haven, this hotel is 1.8 mi (2.9 km) from Wharton Brook State Park and within 6 mi (10 km) of Tradition Golf Club at Wallingford and Toyota ...

                      Best Western Plus North Haven Hotel$98

                      Best Western Plus North Haven Hotel$98

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.