Holiday rentals in Redmond

4.97 out of 5 average rating, 154 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, 618 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, 181 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

4.97 out of 5 average rating, 507 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, 249 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, 248 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"

4.88 out of 5 average rating, 422 reviews

The Little Red Chimney House - 3 BR 2 BA

Originally built in 1944, this is a wonderfully furnished bungalow with 3 queen bedrooms and 2 full bathrooms, which I completely renovated and remodeled. It is a stone's throw from Fred Meyers grocery store and Cascade Lakes Brewery, and within easy walking distance to downtown. This house is at the hub of Central Oregon and sits at the crossroads between Bend (14 miles), Prineville (20 miles), and Sisters (20 miles) and is 10 miles from Smith Rock and 2 miles from the Airport.

4.91 out of 5 average rating, 174 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, 664 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, 590 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, 280 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, 6 reviews

Cabin in Terrebonne

The Rim House, Timeless & Serene

BrittanyRating, 5 stars2 weeks 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 stars2 weeks 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.

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!

4.86 out of 5 average rating, 7 reviews

Townhouse in Redmond

Upscale Eagle Crest Experience

MichelleRating, 5 stars2 weeks ago

Condo was beautiful and comfortable. There was a small snag with our pool passes, but they were quick to fix it! Wish we could have stayed longer, but will look to stay here again

Home in Terrebonne

5 out of 5 average rating, 4 reviews

Modern Retreat with Cascade & Smith Rock Views

NickRating, 5 stars1 month ago

I can’t stress how beautiful this house is! Easily the nicest Airbnb I’ve stayed at anywhere in the world. The proximity to Smith Rock was great, Bend isn’t too far, and the local town is cute! The house itself is an architectural masterpiece with ridiculous views. Stay here!!

Serviced apartment in Bend

4.69 out of 5 average rating, 29 reviews

Luxury in Bend, OR | Bunk Bed Room close to Nature

MeredithRating, 5 stars4 days ago

We had a great stay. It was very quiet, had a lot to offer, and was spacious for three of us. I would highly recommend this particular room for families with littles as the closet is huge to put a pack and play in.