Holiday rentals in Redmond

Dog friendly Home near parks and Dry Canyon

Book your stay today and experience all the comforts of home, with the added bonus of a fantastic location within walking distance to local parks. Located in a quiet neighborhood, it provides a peaceful and tranquil atmosphere. Enjoy a large fenced yard with mature trees, perfect for barbecues and outdoor activities or star gazing in the hammock. The beginning of Dry Canyon trail is only a mile away for walking, running or taking the family for a bike ride. Close to local businesses and dining.

Romantic Farmhouse near Mt. Bachelor

Relax at a peaceful farmhouse for a romantic weekend, or take your time exploring Bend with friends. Baltzor Farm and Guesthouse is fewer than 2 miles from some of Bend's amazing breweries and restaurants. Smith Rock and Mt. Bachelor are both within 30 minutes of the guesthouse. Catch a concert, float the Deschutes, or go on a bike ride. Our relaxing farmhouse has rustic, old-world charm with all of the modern amenities, including a soaking tub, waterfall showerhead, soft linens, and Starlink.

Immaculate, Cozy Home in the Heart of Downtown

This gorgeous, welcoming, solar-powered house offers self check-in, speedy WiFi, and complimentary craft beer and coffee. It's located just a couple blocks from downtown, 5 minutes from the airport, 10 minutes from Crooked River Canyon, 15 minutes from Smith Rock, and 20 minutes from Bend. 4 breweries & 3 taprooms are located less than 6 blocks away, and tons of restaurants & shops are close by. Amazing nearby hiking options abound. This space is half of a duplex. No pets or parties allowed.

Quiet Eagle Crest Townhouse w/ Access to Amenities

Enjoy all that Central OR has to offer in this quiet, end-unit townhouse. Located in Eagle Crest Resort, a 1700-acre resort with one spa, three sports centers, five pools, and three full year-round golf courses, it is the ideal location to enjoy Central OR. This 1400sq ft single-level townhome features a great room with soaring ceilings, walls of windows, a fully stocked kitchen, and plenty of gathering spaces. Perfect for a romantic getaway, fun family weekend, or adventure-filled vacation.

Smith Rock Contemporary

Epic views await at this new contemporary Airbnb suite. Situated atop Cinder Butte, with stunning views of Smith Rock, Mt. Hood, Mt. Jefferson and the Terrebonne valley. Enjoy this 800 sf daylight basement apartment with dedicated entrance and parking, open concept living, laundry, bedroom and custom bath. Luxe accommodation just minutes from Smith Rock State Park. A covered deck with magnificent views will make you feel right at home. Start your day with a gorgeous sunrise over Smith Rock

Pointe of Blessing with hot tub and canyon views

Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South.

Bend Country 4 BR/3 Bth, Amazing 9 Mt View, 9 acre

Plan your vacation getaway and escape the destination resorts at our quiet & peaceful lodge home retreat on 9 private acres just north of Bend, "in the country but not far away"; only 10 min. to restaurants & stores if you need anything. Relax while gazing at the amazing 9 Cascade Mts and overlooking a bend of the legendary Deschutes River. Enjoy some of the many Central OR area activities, Skiing, Golfing, Fishing, Hiking, Rock Climbing, Biking, local Wineries & Micro Breweries, & more.

Downtown Redmond Retreat

Welcome to our charming retreat nestled in the heart of Downtown Redmond! Situated in a quit neighborhood and numerous parks in the Dry Canyon and the vibrant energy of downtown's breweries, restaurants, food carts, and shopping, convenience is at your fingertips. Just a quick 5-minute drive to the airport, 15 minutes to Smith Rock, and 20 minutes to Bend, our location offers easy access to nearby attractions. Step out of your front door, and adventure awaits in every direction...

Blossom Cottage Studio

Keep it simple and take it easy at this peaceful and centrally-located, unique, cozy getaway. The Blossom Cottage Studio is located in a beautiful garden setting. ~The space~ • One Room Studio • 1 Bathroom • Full sized bed (additional cot if needed) •Kitchenette (Refrigerator w/small Freezer, Toaster Oven, Microwave, Blender, Kuerig, etc) •Short walk to the heart of downtown Redmond. The cottage is private and located on the back property of a Gift Boutique Shop and Bakery/Cafe.

Cabin on The Rim

Take it easy at this unique and private getaway. This off the grid studio cabin is located just 10 minutes from Smith Rock and 10 minutes from Lake Billy Chinook. It is positioned on the edge of the Crooked River Gorge with breathtaking views of the canyon. Near the cabin is a trail head to a private hiking trail that takes the adventurer down into the canyon where the scenery is otherworldly. Enjoy a sunset with full cascade Mountain View’s, green pastures, and grazing horses.

Canyon House, Crooked River Ranch

Canyon House sits on the edge of the Deschutes River canyon and has a beautiful and scenic view of 11 mountains and peaks. Your home is a 2 bedroom and 2 bath 1450 sf manufactured home. It is attached to ours and Donna and I live on site family. Your privacy is my first rule and quiet is my second. Yet, you may see me watering plants or checking on the Spa. We are open for a 1 night minimum. Checkout time is strict to allow for cleaning and sanitizing on same day check ins.

Wow Holy Cow Chalet

Wow Holy Cow! will be your first thought when you set foot into this knotty pine walled, sunlit filled chalet. Furnished with everything you need for a fun, family getaway. Channel Maria von Trapp while taking in the beautiful mountain views from the loft space. Have a drink on the deck while your kids search for frogs in the rock feature and shallow creek below. Grill a steak on the bbq and admire the deer who often pass by. DCCA# 1453