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Redmond vacation rentals

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Top-rated vacation rentals in Redmond

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

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Guesthouse 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!

Sep 8 – 15

G$20,679 GYD per night

Apartment in Redmond

4.97 out of 5 average rating, 431 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.

Jan 9 – 16

G$28,046 GYD per night

Guest suite in Terrebonne

4.95 out of 5 average rating, 311 reviews

Comfy & Cozy!

Discounts start at 3 nights! Great place for a work-from-home alternative or get-away. Relax in a separate, quiet suite with dedicated, private entrance and parking. Enjoy the spacious 560 sq ft suite, with comfy queen bed, stocked kitchenette, large living area, and full bathroom. The essentials are here + more! With a stunning view of the Cascade Mountain Range, you can enjoy the beauty of a colorful sunset, and maybe see some wildlife! Only 5 minutes to Smith Rock, grocery, & restaurants.

Sep 3 – 10

G$21,305 GYD per night

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.

Apr 4 – 11

G$19,755 GYD per night

Guest suite in Redmond

4.86 out of 5 average rating, 124 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.

Sep 27 – Oct 4

G$23,288 GYD per night

Home in Terrebonne

4.97 out of 5 average rating, 167 reviews

Pointe of Blessing with hot tub and canyon views

We hope you will enjoy our Pointe of Blessing. We feel our canyon perch is a gift from God-just too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South. Prepare to relax unwind and enjoy spectacular sunrises and moonrises.

Oct 20 – 27

G$34,443 GYD per night

Bungalow in Redmond

4.9 out of 5 average rating, 477 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.

Dec 29 – Jan 5

G$25,611 GYD per night

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!

Jan 7 – 14

G$17,365 GYD per night

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 :)

Oct 26 – Nov 2

G$30,017 GYD per night

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.

Sep 5 – 12

G$24,017 GYD per night

Guesthouse in Terrebonne

4.98 out of 5 average rating, 103 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.

Oct 29 – Nov 5

G$27,961 GYD per night

Apartment 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.

Aug 26 – Sep 2

G$22,451 GYD per night

Vacation rentals for every style

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Unique stays

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Popular amenities for Redmond vacation rentals

Laptop-friendly workspace

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 vacation rentals in Redmond

Home in Terrebonne

4.99 out of 5 average rating, 137 reviews

Smith Rock Hideout - Cascade mountain views

Nov 3 – 10

G$33,826 GYD per night

Home in Redmond

4.97 out of 5 average rating, 236 reviews

Redmond Downtown Retreat

Jul 3 – 10

G$29,706 GYD per night

Home in Redmond

4.87 out of 5 average rating, 339 reviews

The Little Red Chimney House - 3 BR 2 BA

Jul 26 – Aug 2

G$35,039 GYD per night

Home in Terrebonne

4.97 out of 5 average rating, 175 reviews

Terrebonne~High Desert Hideaway~Near Smith Rock

Jul 25 – Aug 1

G$32,921 GYD per night

Home in Terrebonne

4.99 out of 5 average rating, 172 reviews

Smith Rock Gardens

G$41,559 GYD per night

Home in Terrebonne

4.99 out of 5 average rating, 126 reviews

Stunning! Smith Rock • King Beds • Steam Shower

Nov 28 – Dec 5

G$104,345 GYD per night

Home in Bend

4.94 out of 5 average rating, 239 reviews

Beautiful 10 acre farm stay in Tumalo!

Oct 15 – 22

G$29,446 GYD per night

Home in Redmond

4.93 out of 5 average rating, 131 reviews

Rhubarb Cottage - Entire house Dog Friendly!

Oct 10 – 17

G$29,969 GYD per night

Other great vacation rentals in Redmond

Tiny home in Bend

4.95 out of 5 average rating, 106 reviews

The Sunset Bungalow, cozy, private and sweet.

Sep 13 – 20

G$23,800 GYD per night

Guest suite in Redmond

4.95 out of 5 average rating, 157 reviews

Adams Corner, private, comfortable, convenient

May 8 – 15

G$29,292 GYD per night

Guesthouse in Bend

4.97 out of 5 average rating, 576 reviews

Little Sister

Oct 16 – 23

G$20,333 GYD per night

Cabin in Bend

4.99 out of 5 average rating, 430 reviews

Skyliners Getaway

Mar 25 – Apr 1

G$18,720 GYD per night

Guesthouse in Terrebonne

4.9 out of 5 average rating, 250 reviews

Compound Coziness...Terrebonne Guesthouse

Oct 18 – 25

G$18,988 GYD per night

Guest suite in Redmond

4.99 out of 5 average rating, 163 reviews

The Home Inn-Central Oregon Hotspot

Jul 23 – 30

G$35,590 GYD per night

Chalet in Eagle Crest

4.98 out of 5 average rating, 206 reviews

Cozy 3 bdrm + loft Eagle Crest Chalet w/ Hot Tub!

Nov 18 – 25

G$32,524 GYD per night

Guest suite in Prineville

4.93 out of 5 average rating, 219 reviews

Artsy Guest House Nestled in the Rimrock

Aug 30 – Sep 6

G$24,228 GYD per night

Quick stats about vacation 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

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Redmond?
Yes! Work meets play with ease at over 100 vacation rentals in Redmond featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Redmond?
Four-legged friends are welcome in Redmond. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Redmond?
Redmond has more than 110 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in private suite rentals in Redmond?
Experience the best of Redmond with our private suite rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do private suite rentals in Redmond have wifi?
Absolutely! We offer over 10 private suite rentals with wifi in Redmond. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Redmond have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Redmond. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Redmond have air conditioning?
Absolutely! We offer over 100 house rentals with air conditioning in Redmond. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Redmond?
Enhance your stay in our House Rentals with the most popular amenities: over 120 homes with wifi, over 30 homes with a bbq area, over 100 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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