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Holiday rentals 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 house in Redmond

4.84 out of 5 average rating, 228 reviews

The Downtown Guesthouse

This is a BRAND NEW guesthouse in Downtown Redmond. Enjoy a night on the town with an easy 5-7 minute walk to Wild Ride or General Duffy's, both are great food truck lots. Or enjoy a night in cozying up on the couch. We have reliable WiFi for streaming on your devices or on the smart TV provided. If you came to town to enjoy the vast amount of outdoor activities that Central Oregon has to offer then you're in for a treat! Smith Rock (15 min), Mount Bachelor (45min). We know you’ll enjoy it here!

12–19 Sept

Guest favourite

Flat in Redmond

4.98 out of 5 average rating, 427 reviews

Smith Rock View 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.

21–28 Dec

£131 per night

Guest favourite

Home in Redmond

4.82 out of 5 average rating, 518 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.

1–8 Apr

Guest favourite

Guest suite in Redmond

4.86 out of 5 average rating, 121 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.

11–18 Nov

£107 per night

Guest favourite

Home in Redmond

4.94 out of 5 average rating, 120 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

11–18 Oct

£126 per night

Guest favourite

Bungalow in Redmond

4.9 out of 5 average rating, 473 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

27 Nov – 4 Dec

£101 per night

Guest favourite

Guest suite in Redmond

4.93 out of 5 average rating, 247 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!

11–18 Jul

Guest favourite

Tiny home in Redmond

4.99 out of 5 average rating, 187 reviews

Tranquil Views, Close to Smith Rock, Country Cozy

The Tiny House at Aspen View Farm is your next special getaway! Great location for solo travelers or couples exploring beautiful Central Oregon - Smith Rock 15 min away. On a unique 14 acre farm setting, relax and retreat with tranquil Cascade Mountain and country views, plus watch cute grazing sheep. The Tiny is cozy and comfy with quality amenities to make you feel right at home - stocked kitchen, heated floors & more! Please read full listing before booking so there are no surprises :)

9–16 Dec

£137 per night

Guest favourite

Guest suite in Redmond

4.99 out of 5 average rating, 181 reviews

Momma Sal's Studio in Downtown Redmond

Charming, beautiful studio w private entrance, patio, amazing stone fireplace (gas), coffee maker, mini fridge, microwave, glassware, dishes, very nice linens & bath. Downtown, quiet neighborhood. Easy walk to restaurants, shops, great craft brews, events. Dry Canyon few blocks away for disc golf, walking, running, biking, hiking trails. Lovely parks. Close to Expo, 20-30 min to Bend, Smith Rock, Sisters, Prineville. Great C.O. location in every direction for fun & recreation all seasons.

8–15 Aug

£108 per night

Guest favourite

Guest house in Terrebonne

4.98 out of 5 average rating, 101 reviews

Modern lofted guest house

Enjoy our recently completed lofted guest house. Just 3.7 miles from smith rocks and walking distance to Terrebonne restaurants, coffee and local grocery store. Centrally located, 15 min to the airport and just a 30 min drive to Bend. Our guest house has a fully stocked kitchenette ( NO OVEN) with a toaster oven/air fryer, and an induction cook top. Sit back and relax outside in the Adirondack chairs while drinking a Nespresso coffee. Wifi is provided as well as a Roku T.V and DVD.

17–24 Nov

£129 per night

Guest favourite

Home in Redmond

4.97 out of 5 average rating, 235 reviews

Redmond Downtown Retreat

Nice, new home with all the amenities you need for a home-away-from-home stay with alley access and plenty of private parking for 2-3 cars. Centrally located, this home is an easy 2.5 miles to the Redmond airport, 3 miles to Deschutes County Fairgrounds and Expo Center, 15 miles to Smith Rock, 17 miles to Bend, and 20 miles to Sisters. It is an easy walk to several brew pubs and eateries, and to miles of paved and dirt trails, skate park, playground and tennis courts.

3–10 Jul

£135 per night

Guest favourite

Home in Terrebonne

4.99 out of 5 average rating, 135 reviews

Smith Rock Hideout - Cascade mountain views

Just 8 minutes to Smith Rock, the Hideout is a cozy retreat for climbers, hikers, trail runners, digital nomads, and anyone wanting to relax and explore the beauty of Central Oregon. Take in the views of the Cascade mountains and farmland beyond while relaxing on the covered porch or window seat. The Hideout is my personal retreat. While away, I’m happy to share it with outdoor enthusiasts who enjoy creature comforts after a day of getting after it outdoors.

17–24 Dec

£144 per night

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Popular amenities for Redmond holiday rentals

Free parking on premises

Air conditioning

Stay near Redmond's top sights

Walmart Supercenter15 locals recommend

Deschutes County Fairgrounds15 locals recommend

Sam Johnson Park13 locals recommend

Madaline's Grill & Steak House14 locals recommend

Safeway17 locals recommend

Wild Ride Brewing83 locals recommend

Other great holiday rentals in Redmond

Guest favourite

Tiny home in Bend

4.95 out of 5 average rating, 106 reviews

The Sunset Bungalow, cozy, private and sweet.

10–17 Sept

£107 per night

Guest favourite

Guest suite in Bend

4.98 out of 5 average rating, 120 reviews

Bend, Oregon Private Suite; Perfect for 1 or 2

17–24 May

Guest favourite

Guest suite in Bend

4.98 out of 5 average rating, 218 reviews

Portal to the Cascades

2–9 Oct

£101 per night

Guest favourite

Guest suite in Terrebonne

4.95 out of 5 average rating, 310 reviews

Comfy & Cozy!

8–15 Jan

Guest favourite

Cabin in Bend

4.99 out of 5 average rating, 429 reviews

Skyliners Getaway

10–17 Dec

Guest favourite

Guest house in Terrebonne

4.9 out of 5 average rating, 250 reviews

Compound Coziness...Terrebonne Guesthouse

27 Aug – 3 Sept

Guest favourite

Guest suite in Prineville

4.93 out of 5 average rating, 219 reviews

Artsy Guest House Nestled in the Rimrock

20–27 Oct

£106 per night

Tiny home in Bend

4.82 out of 5 average rating, 142 reviews

IT'S A WEE HOUSE

27 Sept – 4 Oct

Quick stats about holiday rentals in Redmond

Total rentals
190 properties
Wifi availability
180 properties include access to wifi
Rentals with dedicated workspaces
100 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
10K reviews

Destinations to explore