Holiday houses in Redmond

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Top-rated holiday rentals in Redmond

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Rental unit in Redmond

4.97 out of 5 average rating, 484 reviews

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 apartment with dedicated entrance and parking, open concept living, laundry, bedroom and custom bath. Luxe accommodation just minutes from Smith Rock State Park. A huge covered deck with magnificent views will make you feel right at home. Get your trip started off right with a gorgeous sunrise over Smith Rock.

Guest favourite

Guesthouse in Terrebonne

4.86 out of 5 average rating, 224 reviews

15 min from SmithRock pets allowed affordable spot

close to smith rock. In the crooked river ranch community. golf course, tennis court, store, 3 bars, all 5 minutes away. Newly renovated guest house. We do live on 4 dusty acres, and are pet friendly, so although we pride ourselves on the cleaning and sanitizing we perform between guests we also ask if you are super picky to please refrain from booking, as this is definitely not a luxury hotel in the city. We try to keep our price the lowest in the area, and strive to attain that 5 star review.

Guest favourite

Guest suite in Redmond

4.85 out of 5 average rating, 165 reviews

Light & bright, clean, private guest suite!

Our private guest suite is filled with natural light, a comfy queen bed and kitchenette. Ideal stay for a get away or just passing through town. Outside the suite you’ll find a covered patio space perfect for a morning cup of coffee or evening glass of wine. To relax, take advantage of the 6-person hot tub and gas fire pit. The location is just 3 minutes from downtown, 10 minutes to Redmond Airport, 20 minutes to Smith Rock, 20 minutes to Bend, approx. 50 minutes to Mt Bachelor and Hoodoo.

Guest favourite

Home in Redmond

4.83 out of 5 average rating, 577 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.

Guest favourite

Home in Redmond

4.96 out of 5 average rating, 157 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

Guest favourite

Bungalow in Redmond

4.91 out of 5 average rating, 538 reviews

Beautifully Renovated 1918 Bungalow

Discover a beautifully renovated historic gem in the heart of Downtown Redmond. This immaculate and cozy home offers convenience, being situated near various dining establishments, brewpubs, coffee shops, food carts and a short 17 min drive to Bend. Luxuriate in high-quality linens, towels, and a relaxing soaking tub for the ultimate in comfort. The fully equipped kitchen is ready for your culinary adventures. Experience a unique and exceptional stay at the charmingly restored 1918 bungalow

Guest favourite

Guest suite in Redmond

4.93 out of 5 average rating, 272 reviews

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!

Guest favourite

Cabin in Culver

4.91 out of 5 average rating, 113 reviews

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.

Guest favourite

Home in Redmond

4.94 out of 5 average rating, 175 reviews

Rhubarb Cottage - Entire house Dog Friendly!

Dog Friendly! Set in charming Old Town Redmond, this cottage has everything to offer for a quick weekend get away or longer stay with family. Only 25 minutes to downtown Bend and less than 10 minutes to the airport. Featuring 3 bedrooms, 2 full bathrooms, full laundry and a cozy kitchen! Gas bbq, expansive back patio, and corn hole boards to enjoy! Cruiser bikes available to ride to breweries or Dry Canyon Trail just minutes away. 2 Dogs max, additional cleaning fee applies.

Guest favourite

Home in Redmond

4.95 out of 5 average rating, 643 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.

Guest favourite

Rental unit in Redmond

4.99 out of 5 average rating, 262 reviews

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.

Guest favourite

Guest suite in Powell Butte

4.96 out of 5 average rating, 189 reviews

Panoramic Mountain View Oasis

Your high desert sanctuary awaits. Enjoy breathtaking panoramic mountain views from your second floor apartment, stargaze in the hot tub, cozy up outside by the wood-burning fireplace, and so much more! Only 2 miles from Brasada Ranch, convenient for weddings and events. Close to world-famous Smith Rock, centrally located between Bend, Redmond, and Prineville for a myriad of outdoor activities. Forget your worries in this serene and peaceful place!