Fall Escapes in Central Oregon Vacations or Weekends

As Central Oregon heads into fall, there is a brief window of time where you can witness the rainbow of fall colors that dot the region. Summer is over, Fall has arrived, the swarms of vacationers are back to school and work, but take advantage of this time and come to Bend to enjoy what it offers. Dig out the scarves, find our fleece-lined jackets and footwear, don our wool caps, and discover great spots to watch trees, breathe fresh mountain air, and enjoy time away from work and day-to-day events. Check out RockingCRvacationrentals.com for 3 uniques places to stay in Bend, Tumalo, and Sisters for places to stay of which each of these has the colors of fall on their properties. Then, where do we go to get that perfect fall photo, if not on our own front porch or in our backyard?

Make at least one visit to Drake Park, where oak trees stand in plenty and the breezes spread the colorful leaves. For the true feeling of fall in Bend, this park is a must-see. Find (or make) piles upon piles of beautifully arrayed fallen leaves. Feeling a little more adventurous?

You need not travel far to find fall colors in the wilds of Central Oregon. Simply drive west about 20 miles. Head over on Highway 20, not far from Sisters. There, on the cusp of where the east side of the Cascades meets the west, you will find the colors of autumn hiding in the most unlikely places. Groves of quaking aspen can be found woven between the color-challenged ponderosas pines. Peer even farther into the unique, as low-lying Vine Maple and Douglas Maples are sprinkled throughout jet-black obsidian flows and other rocky croppings, creating sights visible for a only matter of weeks before snow comes and blankets all that surrounds.

Above Mount Bachelor discover Green Lakes Trail. Follow Fall Creek up to the Green Lakes. You will see Meadow grasses and native Flora in bright yellows and reds among the pines and fir trees, and along the creek. The many rushing waterfalls are surrounded by lush warm Autumn colors. (Insert image: Fall Creek along Green Lakes

The Metolius River is breathtaking all year, but take advantage of less people around and beautiful colors. The Kokanee Salmon and the Rainbow trout are flyfishers’ dreams, but rainbow colors are lush along the river trails right now. The Three Sisters Wilderness Area with its many lakes, rivers, and meadows, has hundreds of miles of trails throughout the Deschutes National Forest.

Schedule yourself a flight over the Central Oregon Cascades out of Sisters or Bend during the transformative weeks of October. There you will see how truly unique our fall is. Autumn is a shorter season than most of us prefer, and gives us brief images along the way, ever-changing. But perhaps that is what makes the high desert fall so special. The season may not last a matter of months like it does in many other regions in the United States, but its seemingly fleeting arrival makes it more worthwhile. So catch it while you can. Stay with us while you explore our changing Autumn palette. Don’t miss it! Check out Rocking CR Vacation Rentals for 3 unique stays. Book Now.

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!


As Business owners, we derive our inspiration from you, our guests.  We love hearing about your adventures and experiences at our vacation rental homes.

We encourage you to leave a comment.  Use this as your digital guest register.  Tell us about that perfect ride or hike up Mackensie Pass, or that epic day skiing and riding on the Mountain, that tranquil day on the Metolius River casting for that Brown or Bull Trout, that spectacular golf game at Eagle Crest, Aspen Lakes, and Black Butte golf courses, or maybe a special coffee place or food you tasted.  Whatever, where-ever, you find your inspiration, tell us about it here and share it with others.

April 10, 2018

Sisters famous "Biggest Little Rodeo" is fast approaching, the famous National Quilt Show is in July along with the small town Old Fashion Fourth of July parade.  Bend has Beer Bus and Beer Tastings scheduled, Les Schwab concerts throughout the year, duck races, food tastings, Farmer's Markets, and more. Find the best steaks in town at Tumalo Steak House and a truly fun atmosphere for everyone at The Bite in Tumalo.  Let us know what experiences you had at these and other events.

April 29, 2018

Last summer the City of Bend finished the neighborhood park just up the street from our vacation rental in Bend, West Hills HideAway.  What a great park for young kids, families were having picnics under the gazebo and dogs can be off leash in some of the areas of the park. Since our vacation rentals, in Bend, Sisters, and Tumalo are pet friendly, take advantage of the many off-leash areas and the downtown areas, restaurants and breweries,  that allow dogs on the patios. The riverfront near Pioneer Park is less than a mile down the hill, Drake Park riverfront is a little over a mile away from our Bend vacation rental. The river at Shevlin Park is a little over a mile away from our Tumalo vacation rental, which in itself is pet friendly with four acres of park to be off leash, fully fenced. Check it out now.

May 3, 2018

Sisters Folk Festival  in September, Quilt Show in July and Music and Brews Festival in August...Check the website for Sisters events. 

June 4, 2018

Fabulous weekend with Bend Brew Chase...a lot of fun.  Individuals and teams of 4 ran 50 miles from Redmond through Sisters to Bend's Les Schwab Amphitheater where they were then rewarded with lots of water, food and brew tastings.  A fun event and friends of ours did awesome.  Congratulations to all runners and to all volunteers along the way!

I would like to call on all creative people: come and stay at one of our vacation homes.  They are inspirational for artists, musicians, writers...You will find yourself surrounded by nature, peace and quiet, gorgeous views everywhere you look, and near enough to lots of activity for inspiration of any kind.  Find your inspiration!

July 2018  Sisters Rhythm and Brews Festival is Friday August 3, 2018.  It is going to rock the park...good music, food, etc.  Don't miss it!

August 2018  Lush forest, alpine lakes, rivers, and high desert characterize the landscape of central Oregon where locals and visitors work up an appetite exploring caves, hiking majestic mountains, and fishing. Bend, the largest city in the county, offers cuisine with local ingredients, upscale steakhouses, and trendy small plates menus. Pine Tavern Restaurant and Bar with 8 decades of experience has patio seating on the Deschutes riverfront and the Brickhouse Restaurant (original one is in Redmond) are excellent.  If you're looking for something more exotic, there's also Mexican cuisine, try El Rodeo or La Rosa, and sushi, try 5 Fusion, to tempt you. Families can stop by one of the pizzerias or chain restaurants for dependable American dishes. You'll also find Thai, Indian, and Italian establishments in addition to a handful of breweries to appeal to a range of palates. For a place to stay, check out our pet friendly vacation rental in Bend, the West Hills HideAway, which is close to all the downtown restaurants, event, and access to activities, but distance enough to relax after activities.

August 2018 SISTER'S FOLK FESTIVAL September 7-9, 2018 is just around the corner.  It is truly the most awesome music festival I have ever attended.  It draws talented musicians from all over the United States and around the world. The folk music you hear and see performed uses so many techniques, styles, instruments, different genres that will take you through time while listening.  The musicians put on jam sessions, mini lessons, mini shows, as well as all the headliners identified. Local breweries offer their newest brews, local food carts are available, and restaurants serving local fare as well.  If you have never gone, please consider it and stay at one of our three vacation homes as your base camp for the weekend.  Our pet friendly vacation rental in Sisters, Oregon, Caroline's Chalet, is the perfect place to stay while attending...or exploring...You will be glad you did.