Holiday rentals in Redmond

4.97 out of 5 average rating, 152 reviews

Flat in Redmond

Large Mountain View Suite on Quiet Acreage

Quiet rural location just a few miles from town on the rimrock above a small canyon. Enjoy a panoramic view of the Cascades from a spacious studio apartment that is comfortable and uncluttered. Features a roomy bathroom, walk-in shower, a small balcony, many windows, and a large walk-in closet. Additional fee for each pet. Roll-away twin bed on req. Nearby attractions: 1) Smith Rock State Park-7 mi 2) Dry Canyon trail-1 mi 3) Redmond Airport-6 mi 4) Redmond-5 mi 5) Sisters-23 mi 6) Bend-22 mi

4.83 out of 5 average rating, 615 reviews

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.

4.96 out of 5 average rating, 180 reviews

Downtown Redmond Loft

Experience the joy of our space! We've poured our hearts into making sure you feel perfectly at home and cared for. Located in the vibrant heart of downtown Redmond, our house is a tranquil oasis nestled amidst the beauty of Dry Canyon's parks and the bustling energy of breweries, restaurants, food carts, and shops. 5-minute drive to the airport, 15 minutes to Smith Rock, and 20 minutes to Bend. We're delighted to share our stylish home – welcome to your unforgettable stay! Cheers, JoHanna

4.93 out of 5 average rating, 284 reviews

Guest suite in Redmond

Spacious and Private Suite in Central Oregon!

Want a spacious, private, comfortable, and clean place to stay for the weekend or business trip with great discounts for week + stays? This might be the place for you! The space is a sports themed, super clean, private living room, bedroom and bathroom near great Central Oregon attractions such as Smith Rock (12mi), Bend (14mi), and Sisters (18mi)! Deschutes County Expo Center and Redmond/Bend airport are within 4 miles. Guests enjoy a private entrance/exit and contactless check in/out!

4.97 out of 5 average rating, 503 reviews

Flat in Redmond

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

4.99 out of 5 average rating, 247 reviews

Home in Terrebonne

Stunning! Smith Rock • King Beds • Steam Shower

A wall of glass provides panoramic views of the iconic Smith Rock formation, creating a seamless connection between the indoor and outdoors. A sleek and sophisticated modern home perched on the rimrock and flooded with sunshine. King beds and a luxurious bathroom with steam shower. Includes Smith Rock Pass. *No parties or pets* (including support animals) please - this is a 'pet-free' home for guests with allergies. Trip insurance recommended if illness, weather or smoke may be an issue.

5 out of 5 average rating, 247 reviews

Tiny home in Redmond

Close to Smith Rock, Mountain View, Country Charm

The Tiny House at Aspen View Farm is just what you need! Great location for exploring beautiful Central Oregon - Smith Rock is only 15 min away. On a unique 14 acre farm, relax and retreat with tranquil Cascade Mountain and country views, say hi to Roo the farm dog, and watch cute grazing sheep. The Tiny is cozy and comfy with quality amenities to make you feel right at home - stocked kitchen, a/c, heated floors & more! Please read full listing before booking so there are no surprises :)

Superhost

Tiny home in Bend

4.84 out of 5 average rating, 206 reviews

IT'S A WEE HOUSE

Quiet, serene, warm and cozy. Relax in this cute little pet friendly WeeHouse with a wee loft. Located in the heart of Central Oregon just minutes from downtown Bend and the Redmond airport. You'll enjoy countryside views of Smith Rock and the valley below. Bask under 1000 year old Juniper trees. High Speed wifi, private bathroom and kitchenette. If this doesn't feel like a fit or is unavailable please check out our other options: "The Sunset Bungalow" and "The Sunrise Studio"

4.91 out of 5 average rating, 170 reviews

Cabin in Culver

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.

4.95 out of 5 average rating, 661 reviews

"Little Pine Cabin" attached to my home.

MASTER SUITE Go hiking, fishing, sight seeing and enjoy upscale steak houses, Sushi Bars, food carts, all within a couple of miles. Then come back to your Little Pine Cabin. Enter into a comfortable living area with a vaulted knotty pine ceiling, propane stove, a dual reclining leather couch. Relax in front of the 42 inch flat screen, a well stocked coffee bar, microwave and a mini-fridge. Similar to a studio apartment. You will enjoy the space and quiet neighborhood.

4.91 out of 5 average rating, 588 reviews

Bungalow in Redmond

Beautifully Renovated 1918 Bungalow

Beautifully restored 1918 bungalow in the heart of Downtown Redmond. Walk to local brewpubs, coffee shops, and food carts. Just 17 miles to Bend. Enjoy luxe linens, plush towels, a soaking tub, and a fully equipped kitchen. Immaculate, cozy, and full of character—this historic gem blends comfort, style, and walkable charm for a memorable stay. Steps from local favorites—food, drinks, and downtown vibes! Perfect base for exploring Smith Rock, and Central Oregon beauty! ⸻

4.99 out of 5 average rating, 278 reviews

Flat in Redmond

Redmond Retreat - stylish studio with full kitchen

Quiet, upscale studio conveniently located in the hub city of Redmond, 3.5 miles to the airport, 7 to Smith Rock, 14 to Bend and 18 to Sisters. Close to restaurants and grocery shopping. Spotlessly clean, with all the personal touches you expect and amenities perfect for two. Fully equipped kitchen, table for meals or work space, Big-screen smart tv (Direct TV service), 5G WiFi, AC. Private parking, direct laundry access. We cannot accommodate pets.

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Other great holiday rentals in Redmond

5 out of 5 average rating, 5 reviews

Cabin in Terrebonne

The Rim House, Timeless & Serene

BrittanyRating, 5 stars1 week ago

Absolutely fabulous hosts. Beautiful views and adorable wildlife (marmot and a pair of quail). Views of Mount Hood in the distance. We felt right at home at the end of a long travel day. Check out these newer hosts; they are awesome!

Superhost

Villa in Redmond

5 out of 5 average rating, 4 reviews

Cascade Lookout

DesireeRating, 5 stars1 week ago

We had a wonderfully relaxing stay overlooking stunning mountains and beautiful forests. Yi’s house was gorgeous, immaculate, and spacious enough for two families to have their privacy and down time. The house is surrounded by hiking and biking trails, had a great community pool to enjoy, and a rooftop hot tub to enjoy the starry nights in. Would definitely book again the next time we’re in town.

JohannRating, 5 stars1 month ago

New place to stay

Comfy 4BR Home for Family Stays

Thanks Felipe, your house was wonderful.

5 out of 5 average rating, 12 reviews

Cozy Quiet Getaway - near RDM airport

KristiRating, 5 starstoday

This is probably the cleanest Airbnb I have ever stayed in! Very nice home, exactly as described in the listing, and very peaceful neighborhood. We enjoyed sitting outside in the morning and evening in the warm weather. I felt the host went above and beyond with the little extra things she did and left for us! Thank you Kelly, the kids got a kick out of the guy all machine! Oh, and I am supposed to tell you they LOVE the “so soft and cuddly” rug in the master bedroom! Would definitely book again next time we are in town!

5 out of 5 average rating, 4 reviews

Bright and Airy Duplex

HyunseongRating, 5 stars1 month ago

We stayed here for about ten days while climbing at Smith Rock, and the place had everything we needed. From hot water and a warm heater to food and more — everything was thoughtfully prepared. Thank you to our host for taking such good care of us!

4.93 out of 5 average rating, 29 reviews

Guest house in Redmond

Marla’s Cozy Shop ADU

GaryRating, 5 stars2 weeks ago

My girlfriend, dog, and I wanted to spend Memorial Day weekend in the Redmond/Bend area and Brady's AUD provided the perfect space for us to rest and relax between all the outdoor activities! Also loved how they offered parking permits for attractions like Smith Rock. Would definitely stay again!

Superhost

4.79 out of 5 average rating, 63 reviews

4-bedroom home near Airport & Bend w/big backyard

NickRating, 5 stars2 months ago

Nice spot close to town. about 5 or 10 min from restaurants in the downtown area. It was nice staying in a quiet neighborhood, yet being so close to down town.