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Orwell Vacations

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

Hotwire can help you find your travel bliss with Orwell 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 Orwell

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 Orwell 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 Orwell well.

Top Hotel Deals

See all 60 Properties in Orwell
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
    Courtyard Middlebury

    Courtyard Middlebury

    309 Court Street, Middlebury
      3.0 out of 5.0
       
       

      This family-friendly Middlebury hotel is located in a rural location, within 1 mi (2 km) of Town Hall Theater, Vermont Folklife Center, and Henry Sheldon Museum ...

      Courtyard Middlebury$125

      Courtyard Middlebury$125
      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
        Middlebury Inn

        Middlebury Inn

        14 Court Square, Middlebury
          3.0 out of 5.0
           
           

          Located in the heart of Middlebury, this spa hotel is within a 15-minute walk of Town Hall Theater and Middlebury College. National Museum of the Morgan Horse ...

          Middlebury Inn$119

          Middlebury Inn$119
          Swift House Inn

          Swift House Inn

          25 Stewart Ln, Middlebury
            3.0 out of 5.0
             
             

            Located in the heart of Middlebury, this golf hotel is within 1 mi (2 km) of National Museum of the Morgan Horse and Middlebury College. Town Hall Theater and ...

            Swift House Inn$144

            Swift House Inn$144
            The Inn on the Green

            The Inn on the Green

            71 South Pleasant St., Middlebury
              3.5 out of 5.0
               
               

              Located in the heart of Middlebury, this guesthouse is within a 15-minute walk of Town Hall Theater and Middlebury College. National Museum of the Morgan Horse ...

              The Inn on the Green$149

              The Inn on the Green$149
              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.