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Sandisfield Vacations

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

Hotwire can help you find your travel bliss with Sandisfield 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 Sandisfield

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 Sandisfield 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 Sandisfield well.

Top Hotel Deals

See all 143 Hotels in Sandisfield
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$127

    Hilton Garden Inn Lenox Pittsfield$127
    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
      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
        Simsbury 1820 House

        Simsbury 1820 House

        731 Hopmeadow St, Simsbury
          4.0 out of 5.0
           
           

          Simsbury 1820 House, a 4-star bed and breakfast, is close to local restaurants, shops, and biking trails, and within a 25-minute drive of historic Hartford sites ...

          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
            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$149

                Cranwell Spa and Golf Resort$149
                Days Inn by Wyndham Torrington

                Days Inn by Wyndham Torrington

                492 East Main St, Torrington
                  2.0 out of 5.0
                   
                   

                  Situated in Torrington, this motel is within 1 mi (2 km) of Hotchkiss-Fyler House Museum, KidsPlay Museum, and Warner Theater. Connecticut Valley Winery is 3 ...

                  Days Inn by Wyndham Torrington$72

                  Days Inn by Wyndham Torrington$72
                  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
                    Black Swan Inn, an Ascend Collection Hotel

                    Black Swan Inn, an Ascend Collection Hotel

                    435 Laurel St, Lee
                      3.0 out of 5.0
                       
                       

                      Situated on a lake, this hotel is within 1 mi (2 km) of Animagic Museum of Animation and Lee Library. Greenock Country Club and The Mount are also within 3 mi ...

                      Black Swan Inn, an Ascend Collection Hotel$105

                      Black Swan Inn, an Ascend Collection Hotel$105

                      Top Flight Deals

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