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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

4.83 out of 5 average rating, 230 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!

13–20 Sep

€ 110 per night

Guest favourite

Flat in Redmond

4.98 out of 5 average rating, 430 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.

20–27 Jan

€ 147 per night

Guest favourite

Home in Redmond

4.82 out of 5 average rating, 520 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.

24–31 Oct

€ 63 per night

Guest favourite

Bungalow in Redmond

4.9 out of 5 average rating, 475 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.

15–22 Feb

€ 132 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!

30 Jul – 6 Aug

€ 90 per night

Guest favourite

Tiny home in Redmond

4.99 out of 5 average rating, 188 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 :)

29 Oct – 5 Nov

€ 168 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.

15–22 Aug

€ 124 per night

Guest favourite

Guest house in Bend

4.94 out of 5 average rating, 539 reviews

Private apt. nestled in the Ponderosa Pines

Nestled among the Ponderosa pines, this newly constructed apartment is a relaxing getaway after a day enjoying Central Oregon. The apartment is completely separate from the main house and comes with a/c and heating. The bedroom has a queen bed. Kitchen has a refrigerator, coffee pot, countertop convection oven, microwave oven and counter top cooktop burner. Large deck with seating and gas grill. Located 2 miles from Peterson Ridge trails, 5 miles from Sisters, 15-25 mins to Bend.

16–23 Oct

€ 94 per night

Guest favourite

Home in Redmond

4.95 out of 5 average rating, 261 reviews

Downtown Redmond Retreat

Welcome to our charming retreat nestled in the heart of Downtown Redmond! Situated amidst the tranquility of 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...

3–10 Jan

€ 145 per night

Guest favourite

Home in Redmond

4.97 out of 5 average rating, 236 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.

5–12 Jul

€ 144 per night

Guest favourite

Home in Terrebonne

4.99 out of 5 average rating, 136 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.

30 Dec – 6 Jan

€ 165 per night

Guest favourite

Flat in Redmond

4.99 out of 5 average rating, 241 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.

29 Sep – 6 Oct

€ 115 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

Home in Terrebonne

4.97 out of 5 average rating, 167 reviews

Pointe of Blessing with hot tub and canyon views

15–22 Oct

€ 170 per night

Guest favourite

Home in Redmond

4.93 out of 5 average rating, 131 reviews

Rhubarb Cottage - Entire house Dog Friendly!

17–24 Dec

€ 161 per night

Guest favourite

Guest house in Terrebonne

4.98 out of 5 average rating, 103 reviews

Modern lofted guest house

5–12 Mar

€ 153 per night

Guest favourite

Guest suite in Redmond

4.95 out of 5 average rating, 157 reviews

Adams Corner, private, comfortable, convenient

11–18 May

€ 156 per night

Guest favourite

Guest house in Terrebonne

4.84 out of 5 average rating, 183 reviews

15 min from SmithRock pets allowed affordable spot

20–25 May

€ 61 per night

Guest favourite

Guest suite in Redmond

4.86 out of 5 average rating, 124 reviews

Light & bright, clean, private guest suite!

24 Sep – 1 Oct

€ 119 per night

Guest favourite

Tiny home in Bend

4.95 out of 5 average rating, 106 reviews

The Sunset Bungalow, cozy, private and sweet.

3–10 Oct

€ 123 per night

Guest favourite

Guest suite in Prineville

4.93 out of 5 average rating, 219 reviews

Artsy Guest House Nestled in the Rimrock

22–29 Sep

€ 122 per night

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

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