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Monterey Vacations

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

Hotwire can help you find your travel bliss with Monterey 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 Monterey

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 Monterey 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 Monterey well.

Top Hotel Deals

See all 136 Hotels in Monterey
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 close to Arrowhead Museum, Bousquet Ski Area, and Kennedy Park. Local attractions also include Canoe Meadows Wildlife Sanctuary ...

    Hilton Garden Inn Lenox Pittsfield$127

    Hilton Garden Inn Lenox Pittsfield$127
    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 spa hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater, and Berkshire Athenaeum. Canoe Meadows Wildlife ...

      Crowne Plaza Pittsfield-Berkshires$91

      Crowne Plaza Pittsfield-Berkshires$91
      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$93

        Yankee Inn$93
        Hampton Inn & Suites Berkshires Lenox

        Hampton Inn & Suites Berkshires Lenox

        445 Pittsfield Rd, Lenox
          2.5 out of 5.0
           
           

          Situated in a rural location, this hotel is close to Arrowhead Museum, Bousquet Ski Area, and Kennedy Park. Local attractions also include Pleasant Valley Wilderness ...

          Hampton Inn & Suites Berkshires Lenox$118

          Hampton Inn & Suites Berkshires Lenox$118
          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 hotel is located in the city center, close to Lake Mansfield Park, Ski Butternut, and Mahaiwe Performing Arts Center. Area attractions also ...

            Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires$161

            Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires$161
            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$152

              Courtyard by Marriott Lenox Berkshires$152
              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$159

                Cranwell Spa and Golf Resort$159
                Berkshire Mountain Lodge

                Berkshire Mountain Lodge

                8 Dan Fox Dr, Pittsfield
                  3.0 out of 5.0
                   
                   

                  Situated in Pittsfield, this lodge is 1 mi (1.7 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and ...

                  Berkshire Mountain Lodge$175

                  Berkshire Mountain Lodge$175
                  Pleasant Valley Motel West Stockbridge

                  Pleasant Valley Motel West Stockbridge

                  42 Stockbridge Rd, West Stockbridge
                    2.0 out of 5.0
                     
                     

                    Situated near the beach in West Stockbridge, this motel is close to Berkshire Botanical Garden, Chesterwood and Norman Rockwell Museum. Area attractions also ...

                    Pleasant Valley Motel West Stockbridge$50

                    Pleasant Valley Motel West Stockbridge$50
                    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$101

                      Black Swan Inn, an Ascend Collection Hotel$101

                      Top Flight Deals

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