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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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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.

Guesthouse in Powell Butte

4.89 out of 5 average rating, 101 reviews

Juniper Bunkhouse - newly renovated!

Enjoy either a relaxing or adventurous getaway located on a rustic ranch. Gorgeous views of Smith Rock, Grizzly Mountain and Cascade Mountains can be seen anywhere on the ranch as it is situated at the base of the Powell Butte. Feel free to take a short, easy hike to the edge of the property where there is a bistro table to sit at and admire the Sisters mountains as well as Mt. Jefferson and Mt. Washington. Walk route map provided at the time of stay. We are excited to share the views with you!

Guest suite in Redmond

4.85 out of 5 average rating, 164 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.

Home in Redmond

4.83 out of 5 average rating, 575 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.

Bungalow in Redmond

4.91 out of 5 average rating, 537 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 suite in Redmond

4.93 out of 5 average rating, 270 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!

Tiny home in Redmond

5 out of 5 average rating, 233 reviews

Tranquil Views, Close to Smith Rock, Country Cozy

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 :)

Guesthouse in Terrebonne

4.98 out of 5 average rating, 134 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.

Cabin in Culver

4.91 out of 5 average rating, 110 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.

Home in Redmond

4.94 out of 5 average rating, 172 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.

Home in Redmond

4.95 out of 5 average rating, 642 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.

Home in Redmond

4.97 out of 5 average rating, 254 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.

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

Smith Rock Brewing Company90 locals recommend

Wild Ride Brewing82 locals recommend

Diego's Spirited Kitchen62 locals recommend

Brickhouse51 locals recommend

One Street Down Cafe48 locals recommend

Redmond Municipal Airport (RDM)31 locals recommend

Redmond homes

Home in Bend

4.98 out of 5 average rating, 118 reviews

Romantic Farmhouse near Mt. Bachelor

Home in Sisters

4.82 out of 5 average rating, 115 reviews

Single level, pet friendly, downtown, cute cottage

Home in Terrebonne

4.96 out of 5 average rating, 173 reviews

Smith Rock Hideout - Cascade mountain views

Home in Bend

4.94 out of 5 average rating, 244 reviews

Beautiful 10 acre farm stay in Tumalo!

Home in Redmond

4.96 out of 5 average rating, 146 reviews

Large Group Comfort - 7 Separated Sleeping Areas!

Home in Bend

4.89 out of 5 average rating, 166 reviews

JJ's Country Oasis Ranch Home on Acerage

Home in Bend

4.97 out of 5 average rating, 382 reviews

Walk to On Tap, Minutes to Downtown Bend, & Garage

Home in Redmond

4.94 out of 5 average rating, 100 reviews

Eagle Crest Resort - 3 bdrm home in Central Oregon

Other great vacation rentals in Redmond

Rental unit in Redmond

4.98 out of 5 average rating, 97 reviews

Mountain View Suite on Quiet Acreage

Cottage in Redmond

4.92 out of 5 average rating, 53 reviews

Blossom Cottage Studio

Guest suite in Bend

4.99 out of 5 average rating, 217 reviews

Private Apartment, Separate Entrance, Spacious

Cabin in Bend

4.92 out of 5 average rating, 109 reviews

Black Duck Cabin

Tiny home in Bend

4.84 out of 5 average rating, 180 reviews

IT'S A WEE HOUSE

Guesthouse in Terrebonne

4.86 out of 5 average rating, 224 reviews

15 min from SmithRock pets allowed affordable spot

Home in Redmond

4.95 out of 5 average rating, 19 reviews

Black Butte Bungalow

Cottage in Redmond

4.94 out of 5 average rating, 35 reviews

The West Minister Square Cottage

Quick stats about vacation rentals in Redmond

Total rentals
200 properties
Total number of reviews
11K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
100 properties have a dedicated workspace
Wifi availability
190 properties include access to wifi

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 hotel rentals in Redmond?
Experience the best of Redmond with our hotel rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Redmond have wifi?
Absolutely! We offer over 120 house rentals with wifi in Redmond. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Redmond have a gym?
Absolutely! We offer over 10 house rentals with a gym 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 private suite rentals in Redmond have air conditioning?
Absolutely! We offer over 10 private suite rentals with air conditioning in Redmond. Enjoy a tailored experience with all the comforts you desire.

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