Dream Winter Vacation Rental in Bend Oregon That Will Blow Your Mind

When it’s time to book your dream vacation rental in Bend, Oregon, you’ve come to the right place. Be right near all of your favorite activities, whether it’s skiing or snowboarding, golfing or hiking, fishing or just eating at some of the best restaurants, Rocking CR Vacation Rentals offers cozy and unique accommodations in Central Oregon.

Come relax in a peaceful setting that will make this vacation the best one yet. If you’re looking for the ultimate vacation spot that will blow your mind, read on for three places that will become your new go to for vacation rentals.

The Best Winter Vacation Rental in Bend, Oregon You'll Never Forget

When you’re looking for a vacation rental in Bend, Oregon, or in surrounding areas, you’re probably imagining amazing views, close to fun activities, with all the amenities that you need for a relaxing stay. Here are our three favorite places that we recommend for a vacation you’ll never forget.

Caroline's Chalet

Come check out this sanctuary in Sisters, Oregon. A charming 2 bedroom, 1 and half bathroom lodge chalet that is nestled at the base of the Cascade Mountains. Caroline’s Chalet is the ideal vacation destination for small families or couples who want to be close to small town amenities but away from the hustle and bustle of the city. Only 3 miles from town, this chalet is a great place to rest and refuel after a day full of adventures, or as a basecamp for quiet relaxation.

This gorgeous home has a floor to ceiling lava rock fireplace with a cozy open living room, and an outside covered porch and a sunny patio. Whether you’re looking for a place to hang out and be comfortable or just a quick resting stop before your Alpine adventure, you can’t go wrong with this adorable winter vacation rental near Bend, Oregon.

Rocking CR Guest House

The Rocking CR Guest House is a beautiful 2 bedroom 1 bathroom house that can sleep 4 guests, so it makes for a great family getaway. Located in Tumalo centered between Bend and Sisters), this guest house is behind the main Rocking CR Ranch House, spread out on 5 acres of beautiful Oregon ranch land. With breathtaking views of the Cascade Mountains, you and your family can enjoy time outside, away from the everyday stress that comes with life.

Feel the peace and tranquility of the Cascade Range around you, with hiking trails all around and views you’ll only find on a postcard. Only ten minutes to Bend, and 15 minutes to Sisters, this is the perfect winter vacation rental if you’re looking for peace of mind, wellness relaxation. Grab the kids and book a trip today!

West Hills HideAway

Ready to plan a family reunion or just need a larger house to accommodate your friends and loved ones or just desire more private space? The newly redecorated West Hills HideAway is the perfect place for a large mixed group of people. With three bedrooms and three bathrooms, this home easily sleeps six people, with two futons available as well. This spacious ranch style home is a great home for anyone looking for adventure in Bend or Central Oregon. Conveniently located in the West Hills, this home is also close to town so you can meet everyone’s needs.

From world class fly fishing and golf, to trails for mountain bikes and hiking enthusiasts, this winter vacation rental in Bend, Oregon is your perfect house to getaway and have the vacation of a lifetime. Bring the whole family or grab your closest friends for a weekend they won’t stop talking about.


All Rocking CR Vacation rentals (reserve today) are equipped with everything you need for an ideal vacation. Plush beds and luxurious lines, down comforters and quilts, wifi internet, cable TV, and a full stocked kitchen, plus an outdoor BBQ, you won’t have a care in the world. Book a vacation for the holidays and find kitchen ware, wine glasses, dishes, pots and pans, baking utensils, table cloths, and more - everything you need to cook for your family.

There are also basic spices provided and a full size refrigerator so you can stay as long as you want. All the bathrooms will greet you with soft and plush towel sets, shampoo and conditioner, lotion, a hair dryer, body wash and more. Your home away from home starts and ends here with us. There’s even a washer and dryer and an iron so you are prepared for whatever adventure awaits you.

We love animals, and all of our winter vacation rentals are pet friendly! Call us for pet fees and more information.

All of our homes are non-smoking, so you can count on only breathing in the fresh Bend, Oregon mountain air and relax this vacation season!


Now that you have a background of the some of the best vacation rentals in Bend, Oregon and surrounding areas, you can book your trip! Available year round, these three places become your home away from home whenever you need to get away.

Don’t settle for a dingy hotel, really relax and plan epic adventures at Rocking CR Vacation Rentals - your new go to destination in Central Oregon. We pride ourselves constantly raising the bar on our services. Our guests needs are important to us, and we want to make sure we provide you with everything you need to get the best value when you stay with us.

Reserve your stay today and let us know if you have any questions. We would love to give our recommendations and help you however we can. We can’t wait to hear how much you love our rentals!