Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Castleton Vacations

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

Hotwire can help you find your travel bliss with Castleton 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 Castleton

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 Castleton 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 Castleton well.

Top Hotel Deals

See all 384 Properties in Castleton
Killington Mountain Lodge, BW Signature Collection

Killington Mountain Lodge, BW Signature Collection

2617 Killington Rd, Killington
    3.5 out of 5.0
     
     

    Conveniently near skiing facilities, this Killington hotel is located in the mountains, within 3 mi (5 km) of Killington Golf Course and Killington Resort, and ...

    Killington Mountain Lodge, BW Signature Collection$84

    Killington Mountain Lodge, BW Signature Collection$84
    Hillside Inn at Killington

    Hillside Inn at Killington

    375 Killington Rd, Killington
      2.0 out of 5.0
       
       

      Conveniently near skiing facilities, this Killington motel is located in the mountains, within 3 mi (5 km) of Gifford Woods State Park and Pico Mountain at Killington ...

      Hillside Inn at Killington$65

      Hillside Inn at Killington$65
      Chalet Killington

      Chalet Killington

      2685 Killington Rd, Killington
        2.5 out of 5.0
         
         

        Conveniently near skiing facilities, this Killington hotel is within 3 mi (5 km) of Killington Golf Course and Killington Resort and close to winter sports such ...

        Chalet Killington$85

        Chalet Killington$85
        Days Inn by Wyndham Rutland/Killington Area

        Days Inn by Wyndham Rutland/Killington Area

        401 Us Route 7 S, Rutland
          2.5 out of 5.0
           
           

          Situated in Rutland, this hotel is 0.9 mi (1.4 km) from Rutland Country Club and within 3 mi (5 km) of Hathaway Farm and Pine Hill Park. Paramount Theater and ...

          Days Inn by Wyndham Rutland/Killington Area$64

          Days Inn by Wyndham Rutland/Killington Area$64
          Comfort Inn Trolley Square

          Comfort Inn Trolley Square

          19 Allen St, Rutland
            2.5 out of 5.0
             
             

            Situated in the business district, this hotel is 0.6 mi (1 km) from Rutland Regional Medical Center and within 12 mi (20 km) of Pico Mountain at Killington Ski ...

            Comfort Inn Trolley Square$71

            Comfort Inn Trolley Square$71
            Killington Grand Resort Hotel

            Killington Grand Resort Hotel

            228 East Mountain Road, Killington
              3.5 out of 5.0
               
               

              Located next to a golf course, this ski-in/ski-out hotel in Killington is within 1 mi (2 km) of Killington Golf Course and Killington Resort and close to winter ...

              Killington Grand Resort Hotel$175

              Killington Grand Resort Hotel$175
              Best Western Inn & Suites Rutland-Killington

              Best Western Inn & Suites Rutland-Killington

              5 Best Western Place, Rutland
                 
                 

                This family-friendly Rutland hotel is located in a rural location, within 3 mi (5 km) of Norman Rockwell Museum of Vermont, Rutland Regional Medical Center and ...

                Best Western Inn & Suites Rutland-Killington$114

                Best Western Inn & Suites Rutland-Killington$114
                Lake Bomoseen Lodge

                Lake Bomoseen Lodge

                2551 Vermont 30N, Bomoseen
                  3.5 out of 5.0
                   
                   

                  Located in Bomoseen, this beachfront lodge is next to a golf course, 0.1 mi (0.1 km) from Prospect Bay Country Club, and within 9 mi (15 km) of Halfmoon Pond ...

                  Lake Bomoseen Lodge$165

                  Lake Bomoseen Lodge$165
                  Quality Inn Rutland

                  Quality Inn Rutland

                  253 S Main St, Rutland
                    2.5 out of 5.0
                     
                     

                    Situated in Rutland, this motel is within 1 mi (2 km) of Vermont State Fairgrounds, Diamond Run Mall, and Rutland Regional Medical Center. Paramount Theater ...

                    Quality Inn Rutland$67

                    Quality Inn Rutland$67
                    Hampton Inn Rutland

                    Hampton Inn Rutland

                    47 Farrell Rd, Rutland
                      2.5 out of 5.0
                       
                       

                      Situated near the airport, this hotel is within 1 mi (2 km) of Diamond Run Mall and Vermont State Fairgrounds. Rutland Regional Medical Center and Paramount ...

                      Hampton Inn Rutland$110

                      Hampton Inn Rutland$110

                      Top Flight Deals

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