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Hillsdale Vacations

Pack those stellar shades. We have Hillsdale 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 Hillsdale – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Hillsdale 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 Hillsdale

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 Hillsdale 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 Hillsdale well.

Top Hotel Deals

See all 200 Hotels in Hillsdale
Holiday House Motel

Holiday House Motel

2871 State Route 23, Hillsdale
    2.0 out of 5.0
     
     

    Situated in a shopping district, this motel is 2.2 mi (3.5 km) from Catamount Ski Area and within 9 mi (15 km) of Taconic Trail State Park and W.E.B. Du Bois ...

    Silvanus Lodge

    Silvanus Lodge

    9350 State Rte 22, Hillsdale
      2.0 out of 5.0
       
       

      Situated in Hillsdale, this motel is close to Catamount Ski Area. Regional attractions also include Mahaiwe Performing Arts Center and Ski Butternut.

      Hilton Garden Inn Lenox Pittsfield

      Hilton Garden Inn Lenox Pittsfield

      1032 South Street, Pittsfield
        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 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and ...

        Hilton Garden Inn Lenox Pittsfield$110

        Hilton Garden Inn Lenox Pittsfield$110
        The Red Lion Inn

        The Red Lion Inn

        30 Main Street, Stockbridge
          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. ...

          The Red Lion Inn$140

          The Red Lion Inn$140
          Crowne Plaza Pittsfield-Berkshires

          Crowne Plaza Pittsfield-Berkshires

          1 West St, Pittsfield
            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 ...

            Crowne Plaza Pittsfield-Berkshires$96

            Crowne Plaza Pittsfield-Berkshires$96
            Yankee Inn

            Yankee Inn

            461 Pittsfield Rd, Lenox
              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 mi (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. ...

              Yankee Inn$92

              Yankee Inn$92
              Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

              Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

              249 Stockbridge Rd, Great Barrington
                2.5 out of 5.0
                 
                 

                This family-friendly Great Barrington hotel is located in the mountains, within 2 mi (3 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. Ski Butternut ...

                Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires$135

                Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires$135
                Berkshire Mountain Lodge

                Berkshire Mountain Lodge

                8 Dan Fox Dr, Pittsfield
                  3.0 out of 5.0
                   
                   

                  Situated in Pittsfield, this lodge is close to Arrowhead Museum, Bousquet Ski Area, and Canoe Meadows Wildlife Sanctuary. Local attractions also include Kennedy ...

                  Berkshire Mountain Lodge$150

                  Berkshire Mountain Lodge$150
                  Courtyard by Marriott Lenox Berkshires

                  Courtyard by Marriott Lenox Berkshires

                  70 Pittsfield Rd, Lenox
                    3.0 out of 5.0
                     
                     

                    Situated in Lenox, this hotel is within 2 mi (3 km) of Kennedy Park, Lenox Library, and Pleasant Valley Wilderness Sanctuary. Ventfort Hall Mansion and Gilded ...

                    Courtyard by Marriott Lenox Berkshires$134

                    Courtyard by Marriott Lenox Berkshires$134
                    Cranwell Spa and Golf Resort

                    Cranwell Spa and Golf Resort

                    55 Lee Road, Lenox
                      3.5 out of 5.0
                       
                       

                      Situated in Lenox, this spa resort is within 2 mi (3 km) of The Mount, Ventfort Hall Mansion and Gilded Age Museum, and Lenox Library. Shakespeare and Company ...

                      Cranwell Spa and Golf Resort$139

                      Cranwell Spa and Golf Resort$139

                      Top Flight Deals

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