Holiday Rentals in Bend - Holiday Lettings - Villas

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160 Holiday homes

    24

    Bend ski condo to rent.

    Central Oregon / Bend

    2 4 60 nights min

    • 2 bedrooms
    • sleeps 4
    • 60 nights min
    • Ski
    • Child friendly
    • Air conditioning
    Match: Property type Fishing All filters match

    from £105 / night

    £735 / week

    Book View

    from £105 / night

    These homes match some but not all of your filters. Clear all filters

      21

      Home rental in Bend

      Central Oregon / Bend

      3 6 2 nights min

      • 3 bedrooms
      • sleeps 6
      • 2 nights min
      • Child friendly
      • Air conditioning
      • Private garden
      1 of 2 match: Property type, Fishing 1 of 2 filters match

      from £179 / night

      £1,254 / week

      Book View

      from £179 / night

        36

        Bend holiday home rental

        Central Oregon / Bend

        2 5 2 nights min

        • 2 bedrooms
        • sleeps 5
        • 2 nights min
        • Swimming pool
        • Child friendly
        • Air conditioning
        1 of 2 match: Property type, Fishing 1 of 2 filters match

        from £116 / night

        £813 / week

        Book View

        Responds fast!
        avg. 2 hours 17 minutes

        from £116 / night

          10

          Bend holiday studio rental

          Central Oregon / Bend

          Studio 3 2 nights min

          • Studio
          • sleeps 3
          • 2 nights min
          • Air conditioning
          • Pet friendly
          1 of 2 match: Property type, Fishing 1 of 2 filters match

          from £68 / night

          £473 / week

          Book View

          Responds fast!
          avg. 1 hour 36 minutes

          from £68 / night

            25

            Ski home to rent in Bend

            Central Oregon / Bend

            4 10 min stay varies

            • 4 bedrooms
            • sleeps 10
            • min stay varies
            • Ski
            • Child friendly
            • Pet friendly
            1 of 2 match: Property type, Fishing 1 of 2 filters match

            from £140 / night

            £976 / week

            Book View

            Responds fast!
            avg. 17 minutes

            from £140 / night

              28

              Holiday home in Bend

              Central Oregon / Bend

              2 4 min stay varies

              • 2 bedrooms
              • sleeps 4
              • min stay varies
              • Child friendly
              • Car not necessary
              • Air conditioning
              1 of 2 match: Property type, Fishing 1 of 2 filters match

              from £83 / night

              £580 / week

              Book View

              Responds fast!
              avg. 3 hours 51 minutes

              from £83 / night

                40

                Holiday home in Bend

                Central Oregon / Bend

                4 8 min stay varies

                • 4 bedrooms
                • sleeps 8
                • min stay varies
                • Child friendly
                • Car not necessary
                • Air conditioning
                1 of 2 match: Property type, Fishing 1 of 2 filters match

                from £159 / night

                £1,109 / week

                Book View

                Responds fast!
                avg. 3 hours 51 minutes

                from £159 / night

                  30

                  Holiday home in Bend

                  Central Oregon / Bend

                  3 8 min stay varies

                  • 3 bedrooms
                  • sleeps 8
                  • min stay varies
                  • Child friendly
                  • Car not necessary
                  • Pet friendly
                  1 of 2 match: Property type, Fishing 1 of 2 filters match

                  from £113 / night

                  £788 / week

                  Book View

                  Responds fast!
                  avg. 3 hours 51 minutes

                  from £113 / night

                    39

                    Home rental in Bend

                    Central Oregon / Bend

                    3 6 min stay varies

                    • 3 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Child friendly
                    • Car not necessary
                    • Air conditioning
                    1 of 2 match: Property type, Fishing 1 of 2 filters match

                    from £113 / night

                    £788 / week

                    Book View

                    Responds fast!
                    avg. 3 hours 51 minutes

                    from £113 / night

                      39

                      Home rental in Bend

                      Central Oregon / Bend

                      5 12 min stay varies

                      • 5 bedrooms
                      • sleeps 12
                      • min stay varies
                      • Child friendly
                      • Car not necessary
                      • Air conditioning
                      1 of 2 match: Property type, Fishing 1 of 2 filters match

                      from £367 / night

                      £2,570 / week

                      Book View

                      Responds fast!
                      avg. 3 hours 51 minutes

                      from £367 / night

                        12

                        Home rental in Bend

                        Central Oregon / Bend

                        3 6 2 nights min

                        • 3 bedrooms
                        • sleeps 6
                        • 2 nights min
                        • Child friendly
                        • Air conditioning
                        • Pet friendly
                        1 of 2 match: Property type, Fishing 1 of 2 filters match

                        from £269 / night

                        £1,800 / week

                        Book View

                        from £269 / night

                          28

                          Holiday home in Bend

                          Central Oregon / Bend

                          4 8 min stay varies

                          • 4 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Child friendly
                          • Air conditioning
                          1 of 2 match: Property type, Fishing 1 of 2 filters match

                          from £315 / night

                          £2,204 / week

                          Book View

                          Responds fast!
                          avg. 8 minutes

                          from £315 / night

                            25

                            Bend ski cottage to rent.

                            Central Oregon / Bend

                            1 4 min stay varies

                            • 1 bedroom
                            • sleeps 4
                            • min stay varies
                            • Ski
                            • Child friendly
                            1 of 2 match: Property type, Fishing 1 of 2 filters match

                            from £122 / night

                            £851 / week

                            Book View

                            Responds fast!
                            avg. 17 minutes

                            from £122 / night

                            (2) Excellent 

                              34

                              Holiday guest house in Bend

                              Central Oregon / Bend

                              7 28 2 nights min

                              • 7 bedrooms
                              • sleeps 28
                              • 2 nights min
                              • Car not necessary
                              • Air conditioning
                              • Private garden
                              1 of 2 match: Property type, Fishing 1 of 2 filters match

                              from £648 / night

                              £4,534 / week

                              Book View

                              from £648 / night

                                32

                                Holiday home in Bend

                                Central Oregon / Bend

                                2 6 min stay varies

                                • 2 bedrooms
                                • sleeps 6
                                • min stay varies
                                • Child friendly
                                • Car not necessary
                                • Air conditioning
                                1 of 2 match: Property type, Fishing 1 of 2 filters match

                                from £137 / night

                                £958 / week

                                Book View

                                Responds fast!
                                avg. 1 hour 48 minutes

                                from £137 / night

                                  45

                                  Log cabin rental in Bend

                                  Central Oregon / Bend

                                  2 6 min stay varies

                                  • 2 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Child friendly
                                  • Pet friendly
                                  • Private garden
                                  1 of 2 match: Property type, Fishing 1 of 2 filters match

                                  from £260 / night

                                  £2,068 / week

                                  Book View

                                  from £260 / night

                                    26

                                    Bend ski home to rent.

                                    Central Oregon / Bend

                                    3 6 4 nights min

                                    • 3 bedrooms
                                    • sleeps 6
                                    • 4 nights min
                                    • Ski
                                    • Child friendly
                                    • Air conditioning
                                    1 of 2 match: Property type, Fishing 1 of 2 filters match

                                    from £284 / night

                                    £1,984 / week

                                    Book View

                                    Responds fast!
                                    avg. 17 minutes

                                    from £284 / night

                                      28

                                      Holiday home with golf nearby in Bend

                                      Central Oregon / Bend

                                      2 6 min stay varies

                                      • 2 bedrooms
                                      • sleeps 6
                                      • min stay varies
                                      • Child friendly
                                      • Car not necessary
                                      • Air conditioning
                                      1 of 2 match: Property type, Fishing 1 of 2 filters match

                                      from £246 / night

                                      £1,720 / week

                                      Book View

                                      Responds fast!
                                      avg. 3 hours 51 minutes

                                      from £246 / night

                                        39

                                        Holiday home with shared pool, golf nearby in Bend

                                        Central Oregon / Bend

                                        3 10 min stay varies

                                        • 3 bedrooms
                                        • sleeps 10
                                        • min stay varies
                                        • Swimming pool
                                        • Child friendly
                                        • Car not necessary
                                        1 of 2 match: Property type, Fishing 1 of 2 filters match

                                        from £130 / night

                                        £907 / week

                                        Book View

                                        Responds fast!
                                        avg. 3 hours 51 minutes

                                        from £130 / night

                                          59

                                          Holiday home with shared pool, golf nearby in Bend

                                          Central Oregon / Bend

                                          6 16 min stay varies

                                          • 6 bedrooms
                                          • sleeps 16
                                          • min stay varies
                                          • Swimming pool
                                          • Child friendly
                                          • Car not necessary
                                          1 of 2 match: Property type, Fishing 1 of 2 filters match

                                          from £272 / night

                                          £1,902 / week

                                          Book View

                                          Responds fast!
                                          avg. 3 hours 51 minutes

                                          from £272 / night

                                            34

                                            Bend holiday home rental

                                            Central Oregon / Bend

                                            3 8 min stay varies

                                            • 3 bedrooms
                                            • sleeps 8
                                            • min stay varies
                                            • Swimming pool
                                            • Child friendly
                                            • Car not necessary
                                            1 of 2 match: Property type, Fishing 1 of 2 filters match

                                            from £113 / night

                                            £788 / week

                                            Book View

                                            Responds fast!
                                            avg. 3 hours 51 minutes

                                            from £113 / night

                                            (11) Excellent 

                                              18

                                              Holiday home in Bend

                                              Central Oregon / Bend

                                              3 7 2 nights min

                                              • 3 bedrooms
                                              • sleeps 7
                                              • 2 nights min
                                              • Child friendly
                                              • Private garden
                                              1 of 2 match: Property type, Fishing 1 of 2 filters match
                                              “Great location, beautiful corner of the Cascades!” This home was just perfect for our group of 3 couples who get together each year for some some fun in the mountains. We love backcountry ski touring, cycling, trail running, campfires, and breweries - and Bend has it all! The outdoor fireplace and hot tub made a perfect place to unwind after a long day in the mountains, and the location of this home was very convenient to either head into town, up to the mountains, or just step out the door for miles of road to explore on the run or bike. Each of the 3 bedrooms were cozy and comfortable, and we made good use of the well appointed kitchen and barbecue for home cooked meals. We went into town a couple of nights to sample some of the many microbreweries - 10 Barrel and Good Life being two of our favorites. From the common location at the base of Mt. Bachelor, our group was able to xc ski, backcountry skin up to Broken Top/Sisters Wilderness, or downhill ski, and then meet back up at the end of the day without any hassle. The owner was very helpful in answering our questions and represented the property accurately. We would without hesitation stay at Tumalo Pines again!

                                              from £225 / night

                                              £1,575 / week

                                              Book View

                                              Responds fast!
                                              avg. 3 hours 4 minutes

                                              from £225 / night

                                                36

                                                Bend ski cottage to rent.

                                                Central Oregon / Bend

                                                1 4 2 nights min

                                                • 1 bedroom
                                                • sleeps 4
                                                • 2 nights min
                                                • Nearest beach 200 km
                                                • Ski
                                                • Child friendly
                                                1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                from £68 / night

                                                £473 / week

                                                Book View

                                                from £68 / night

                                                (8) Excellent 

                                                  33

                                                  Holiday home in Bend

                                                  Central Oregon / Bend

                                                  3 9 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 9
                                                  • min stay varies
                                                  • Child friendly
                                                  • Car not necessary
                                                  1 of 2 match: Property type, Fishing 1 of 2 filters match
                                                  “Wonderful vacation” We loved our stay here! The house is furnished beautifully and the scenery is very nice and relaxing. We were very comfortable and enjoyed the privacy though also enjoyed the fun things to do in sunriver. We will definitely return.

                                                  from £113 / night

                                                  £788 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 1 hour 48 minutes

                                                  from £113 / night

                                                    28

                                                    Ski home to rent in Bend

                                                    Central Oregon / Bend

                                                    4 8 min stay varies

                                                    • 4 bedrooms
                                                    • sleeps 8
                                                    • min stay varies
                                                    • Ski
                                                    • Child friendly
                                                    • Air conditioning
                                                    1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                    from £171 / night

                                                    £1,197 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 8 minutes

                                                    from £171 / night

                                                      52

                                                      Holiday home with shared pool, golf nearby in Bend

                                                      Central Oregon / Bend

                                                      6 16 min stay varies

                                                      • 6 bedrooms
                                                      • sleeps 16
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Car not necessary
                                                      1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                      from £290 / night

                                                      £2,028 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 1 hour 48 minutes

                                                      from £290 / night

                                                        24

                                                        Bend ski home to rent.

                                                        Central Oregon / Bend

                                                        3 7 min stay varies

                                                        • 3 bedrooms
                                                        • sleeps 7
                                                        • min stay varies
                                                        • Ski
                                                        • Child friendly
                                                        • Air conditioning
                                                        1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                        from £149 / night

                                                        £1,039 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 8 minutes

                                                        from £149 / night

                                                          30

                                                          Home rental in Bend with shared pool, golf nearby

                                                          Central Oregon / Bend

                                                          3 6 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child friendly
                                                          1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                          from £99 / night

                                                          £693 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 27 minutes

                                                          from £99 / night

                                                            26

                                                            Ski home to rent in Bend

                                                            Central Oregon / Bend

                                                            3 10 min stay varies

                                                            • 3 bedrooms
                                                            • sleeps 10
                                                            • min stay varies
                                                            • Ski
                                                            • Child friendly
                                                            • Air conditioning
                                                            1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                            from £356 / night

                                                            £2,488 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 8 minutes

                                                            from £356 / night

                                                              26

                                                              Ski log cabin to rent in Bend

                                                              Central Oregon / Bend

                                                              3 7 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 7
                                                              • min stay varies
                                                              • Ski
                                                              • Child friendly
                                                              • Pet friendly
                                                              1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                              from £131 / night

                                                              £914 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 8 minutes

                                                              from £131 / night

                                                                26

                                                                Ski home to rent in Bend

                                                                Central Oregon / Bend

                                                                4 12 min stay varies

                                                                • 4 bedrooms
                                                                • sleeps 12
                                                                • min stay varies
                                                                • Ski
                                                                • Child friendly
                                                                • Air conditioning
                                                                1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                                from £140 / night

                                                                £976 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 8 minutes

                                                                from £140 / night

                                                                  33

                                                                  Home rental in Bend with shared pool, golf nearby

                                                                  Central Oregon / Bend

                                                                  3 8 min stay varies

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Car not necessary
                                                                  1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                                  from £113 / night

                                                                  £788 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 1 hour 32 minutes

                                                                  from £113 / night

                                                                  (1) Excellent 

                                                                    29

                                                                    Holiday home with golf nearby in Bend

                                                                    Central Oregon / Bend

                                                                    5 12 2 nights min

                                                                    • 5 bedrooms
                                                                    • sleeps 12
                                                                    • 2 nights min
                                                                    • Child friendly
                                                                    • Air conditioning
                                                                    1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                                    from £359 / night

                                                                    £2,513 / week

                                                                    Book View

                                                                    from £359 / night

                                                                      25

                                                                      Bend ski home to rent.

                                                                      Central Oregon / Bend

                                                                      4 12 min stay varies

                                                                      • 4 bedrooms
                                                                      • sleeps 12
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Ski
                                                                      • Child friendly
                                                                      1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                                      from £176 / night

                                                                      £1,228 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 17 minutes

                                                                      from £176 / night

                                                                        14

                                                                        Bend ski home to rent.

                                                                        Central Oregon / Bend

                                                                        3 6 2 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • 2 nights min
                                                                        • Ski
                                                                        • Child friendly
                                                                        1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                                        from £180 / night

                                                                        £1,260 / week

                                                                        Book View

                                                                        from £180 / night

                                                                        (7) Excellent 

                                                                          22

                                                                          Hotel apartment rental in Bend

                                                                          Central Oregon / Bend

                                                                          1 5 2 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 5
                                                                          • 2 nights min
                                                                          • Swimming pool
                                                                          • Child friendly
                                                                          • Air conditioning
                                                                          1 of 2 match: Property type, Fishing 1 of 2 filters match

                                                                          from £135 / night

                                                                          £810 / week

                                                                          Book View

                                                                          from £135 / night

                                                                          (72) Excellent 

                                                                            29

                                                                            Holiday cottage with golf nearby in Bend

                                                                            Central Oregon / Bend

                                                                            1 4 min stay varies

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • min stay varies
                                                                            • Nearest beach 2 km
                                                                            • Child friendly
                                                                            • Car not necessary
                                                                            1 of 2 match: Property type, Fishing 1 of 2 filters match
                                                                            “The perfect place to stay in Bend!” We loved everything about our stay in Bend. The 2nd Street Cottage was awesome... Clean, quiet, close to downtown and very relaxing! Don is an incredible host, making sure we were enjoying our time. He even surprised us with a bottle of champagne for our anniversary night! He gave us directions to great hikes and a wonderful drive, perhaps one of most memorable times of the trip. The patio is wonderful, wish we could have enjoyed that more. The only problem with our stay was that we didn't stay longer! We would love to return someday, maybe bring the kids next time!

                                                                            from £139 / night

                                                                            £972 - £1,075 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 10 minutes

                                                                            from £139 / night

                                                                            (6) Very Good 

                                                                            Certificate of Excellence

                                                                              15

                                                                              Condo rental in Bend

                                                                              Central Oregon / Bend

                                                                              1 4 2 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • 2 nights min
                                                                              • Child friendly
                                                                              • Air conditioning
                                                                              1 of 2 match: Fishing, Property type 1 of 2 filters match

                                                                              Certificate of Excellence

                                                                              from £104 / night

                                                                              £585 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 1 hour 40 minutes

                                                                              from £104 / night

                                                                              (7) Excellent 

                                                                                42

                                                                                Holiday condo in Bend

                                                                                Central Oregon / Bend

                                                                                3 8 1 night min

                                                                                • 3 bedrooms
                                                                                • sleeps 8
                                                                                • 1 night min
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Air conditioning
                                                                                1 of 2 match: Fishing, Property type 1 of 2 filters match

                                                                                from £161 / night

                                                                                £1,057 / week

                                                                                Book View

                                                                                from £161 / night

                                                                                  24

                                                                                  Holiday condo in Bend

                                                                                  Central Oregon / Bend

                                                                                  3 8 min stay varies

                                                                                  • 3 bedrooms
                                                                                  • sleeps 8
                                                                                  • min stay varies
                                                                                  • Child friendly
                                                                                  1 of 2 match: Fishing, Property type 1 of 2 filters match

                                                                                  from £117 / night

                                                                                  £819 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 3 hours 22 minutes

                                                                                  from £117 / night

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