Holiday Rentals in Bend - Holiday Lettings - Villas

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183 Holiday homes

(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
    Array of 0 match: Array of 0 filters match

    from £655 / night

    £4,584 / week

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    from £655 / night

    (16) Very Good 

      19

      Home rental in Bend

      Central Oregon / Bend

      2 6 2 nights min

      • 2 bedrooms
      • sleeps 6
      • 2 nights min
      • Child friendly
      • Air conditioning
      • Pet friendly
      Match: Property type Garden All filters match

      from £132 / night

      £924 / week

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      from £132 / 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
        Array of 0 match: Array of 0 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 £140 / night

        £983 - £1,087 / week

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        Responds fast!
        avg. 21 minutes

        from £140 / 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
          Array of 0 match: Array of 0 filters match

          from £263 / night

          £2,092 / week

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          from £263 / night

          (3) Excellent 

            16

            Holiday guest house in Bend

            Central Oregon / Bend

            1 4 2 nights min

            • 1 bedroom
            • sleeps 4
            • 2 nights min
            • Child friendly
            • Air conditioning
            • Pet friendly
            Array of 0 match: Array of 0 filters match

            from £87 / night

            £605 / week

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            from £87 / 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
              Array of 0 match: Array of 0 filters match

              from £69 / night

              £478 / week

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              from £69 / night

              (3) Excellent 

              Certificate of Excellence

                31

                Holiday apartment with golf nearby in Bend

                Central Oregon / Bend

                1 4 2 nights min

                • 1 bedroom
                • sleeps 4
                • 2 nights min
                • Child friendly
                • Air conditioning
                • Pet friendly
                Array of 0 match: Array of 0 filters match

                Certificate of Excellence

                from £90 / night

                £592 / week

                Book View

                Responds fast!
                avg. 1 hour 40 minutes

                from £90 / 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
                  Match: Property type Garden All filters match

                  from £249 / night

                  £1,738 / week

                  Book View

                  Responds fast!
                  avg. 2 minutes

                  from £249 / 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
                    Match: Property type Garden All 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 £227 / night

                    £1,586 / week

                    Book View

                    Responds fast!
                    avg. 3 hours 4 minutes

                    from £227 / night

                    (1) Excellent 

                      12

                      Bend holiday home rental

                      Central Oregon / Bend

                      3 6 2 nights min

                      • 3 bedrooms
                      • sleeps 6
                      • 2 nights min
                      • Child friendly
                      • Air conditioning
                      • Private garden
                      Match: Property type Garden All filters match

                      from £137 / night

                      £955 / week

                      Book View

                      from £137 / 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
                        Match: Property type Garden All filters match

                        from £272 / night

                        £1,819 / week

                        Book View

                        from £272 / night

                          38

                          Bend holiday home rental

                          Central Oregon / Bend

                          3 6 min stay varies

                          • 3 bedrooms
                          • sleeps 6
                          • min stay varies
                          • Child friendly
                          • Car not necessary
                          • Air conditioning
                          Match: Property type Garden All filters match

                          from £90 / night

                          £624 / week

                          Book View

                          Responds fast!
                          avg. 2 minutes

                          from £90 / night

                            27

                            Bend holiday home rental

                            Central Oregon / Bend

                            3 6 2 nights min

                            • 3 bedrooms
                            • sleeps 6
                            • 2 nights min
                            • Child friendly
                            • Car not necessary
                            • Air conditioning
                            Match: Property type Garden All filters match

                            from £105 / night

                            £733 / week

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                            Responds fast!
                            avg. 2 minutes

                            from £105 / night

                              29

                              Holiday home in Bend

                              Central Oregon / Bend

                              6 13 min stay varies

                              • 6 bedrooms
                              • sleeps 13
                              • min stay varies
                              • Child friendly
                              • Car not necessary
                              • Air conditioning
                              Match: Property type Garden All filters match

                              from £194 / night

                              £1,356 / week

                              Book View

                              Responds fast!
                              avg. 2 minutes

                              from £194 / 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
                                Match: Property type Garden All filters match

                                from £153 / night

                                £1,070 / week

                                Book View

                                Responds fast!
                                avg. 2 minutes

                                from £153 / night

                                  15

                                  Bend holiday home rental

                                  Central Oregon / Bend

                                  5 12 min stay varies

                                  • 5 bedrooms
                                  • sleeps 12
                                  • min stay varies
                                  • Child friendly
                                  • Air conditioning
                                  • Private garden
                                  Match: Property type Garden All filters match

                                  from £269 / night

                                  £1,897 - £2,706 / week

                                  Book View

                                  from £269 / night

                                    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
                                    Match: Property type Garden All filters match

                                    from £181 / night

                                    £1,267 / week

                                    Book View

                                    from £181 / night

                                      28

                                      Holiday home in Bend

                                      Central Oregon / Bend

                                      3 12 2 nights min

                                      • 3 bedrooms
                                      • sleeps 12
                                      • 2 nights min
                                      • Swimming pool
                                      • Child friendly
                                      • Air conditioning
                                      Match: Property type Garden All filters match

                                      from £360 / night

                                      £2,515 / week

                                      Book View

                                      from £360 / night

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

                                        21

                                        Holiday home accommodation

                                        Central Oregon / Bend

                                        4 8 30 nights min

                                        • 4 bedrooms
                                        • sleeps 8
                                        • 30 nights min
                                        • Swimming pool
                                        • Child friendly
                                        • Air conditioning
                                        1 of 2 match: Garden, Property type 1 of 2 filters match

                                        from £699 / night

                                        £4,892 / week

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                                        from £699 / night

                                        (1) Excellent 

                                          16

                                          Bend holiday home rental

                                          Central Oregon / Bend

                                          5 12 min stay varies

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

                                          from £227 / night

                                          £1,586 - £2,157 / week

                                          Book View

                                          Responds fast!
                                          avg. 32 minutes

                                          from £227 / night

                                          (4) Very Good 

                                            22

                                            Holiday home rental

                                            Central Oregon / Bend

                                            3 8 2 nights min

                                            • 3 bedrooms
                                            • sleeps 8
                                            • 2 nights min
                                            • Beach / lakeside relaxation
                                            • Child friendly
                                            • Pet friendly
                                            1 of 2 match: Garden, Property type 1 of 2 filters match

                                            from £178 / night

                                            £1,242 / week

                                            Book View

                                            Responds fast!
                                            avg. 34 minutes

                                            from £178 / 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: Garden, Property type 1 of 2 filters match

                                              from £360 / night

                                              £2,515 / week

                                              Book View

                                              Responds fast!
                                              avg. 26 minutes

                                              from £360 / 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: Garden, Property type 1 of 2 filters match

                                                from £178 / night

                                                £1,242 / week

                                                Book View

                                                Responds fast!
                                                avg. 26 minutes

                                                from £178 / 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: Garden, Property type 1 of 2 filters match

                                                  from £319 / night

                                                  £2,229 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 26 minutes

                                                  from £319 / 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: Garden, Property type 1 of 2 filters match

                                                    from £85 / night

                                                    £592 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 2 minutes

                                                    from £85 / night

                                                      38

                                                      Bend holiday home rental

                                                      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: Garden, Property type 1 of 2 filters match

                                                      from £100 / night

                                                      £694 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 2 minutes

                                                      from £100 / night

                                                        38

                                                        Home rental in Bend

                                                        Central Oregon / Bend

                                                        1 4 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Child friendly
                                                        • Car not necessary
                                                        1 of 2 match: Garden, Property type 1 of 2 filters match

                                                        from £69 / night

                                                        £478 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 2 minutes

                                                        from £69 / 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: Garden, Property type 1 of 2 filters match

                                                          from £110 / night

                                                          £771 / week

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                                                          Responds fast!
                                                          avg. 2 minutes

                                                          from £110 / 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: Garden, Property type 1 of 2 filters match

                                                            from £114 / night

                                                            £796 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 2 minutes

                                                            from £114 / 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: Garden, Property type 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 £114 / night

                                                              £796 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 2 minutes

                                                              from £114 / 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: Garden, Property type 1 of 2 filters match

                                                                from £374 / night

                                                                £2,617 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 2 minutes

                                                                from £374 / night

                                                                  29

                                                                  Home rental in Bend

                                                                  Central Oregon / Bend

                                                                  1 4 min stay varies

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

                                                                  from £80 / night

                                                                  £561 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 2 minutes

                                                                  from £80 / night

                                                                    46

                                                                    Holiday home in Bend

                                                                    Central Oregon / Bend

                                                                    4 12 min stay varies

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

                                                                    from £512 / night

                                                                    £3,578 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 2 minutes

                                                                    from £512 / night

                                                                    (2) Excellent 

                                                                      30

                                                                      Bend holiday home rental

                                                                      Central Oregon / Bend

                                                                      3 8 2 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 8
                                                                      • 2 nights min
                                                                      • Child friendly
                                                                      • Pet friendly
                                                                      1 of 2 match: Garden, Property type 1 of 2 filters match

                                                                      from £228 / night

                                                                      £1,365 / week

                                                                      Book View

                                                                      from £228 / 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: Garden, Property type 1 of 2 filters match

                                                                        from £182 / night

                                                                        £1,274 / week

                                                                        Book View

                                                                        from £182 / night

                                                                          16

                                                                          Bend holiday home rental

                                                                          Central Oregon / Bend

                                                                          3 7 1 night min

                                                                          • 3 bedrooms
                                                                          • sleeps 7
                                                                          • 1 night min
                                                                          • Child friendly
                                                                          • Pet friendly
                                                                          1 of 2 match: Garden, Property type 1 of 2 filters match

                                                                          from £109 / night

                                                                          £758 / week

                                                                          Book View

                                                                          from £109 / night

                                                                          (3) Excellent 

                                                                            8

                                                                            Holiday home in Bend

                                                                            Central Oregon / Bend

                                                                            1 4 1 night min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 1 night min
                                                                            • Beach / lakeside relaxation
                                                                            • Pet friendly
                                                                            1 of 2 match: Garden, Property type 1 of 2 filters match

                                                                            from £137 / night

                                                                            £664 - £1,146 / week

                                                                            Book View

                                                                            from £137 / night

                                                                            (4) Excellent 

                                                                              31

                                                                              Holiday home rental

                                                                              Central Oregon / Bend

                                                                              5 12 min stay varies

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

                                                                              from £364 / night

                                                                              £2,729 - £3,047 / week

                                                                              Book View

                                                                              from £364 / 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: Garden, Property type 1 of 2 filters match

                                                                                from £136 / night

                                                                                £949 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 2 minutes

                                                                                from £136 / 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: Garden, Property type 1 of 2 filters match

                                                                                  from £141 / night

                                                                                  £987 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 2 minutes

                                                                                  from £141 / night

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