Vacation rentals in Redmond
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Quick stats about vacation rentals in Redmond
Total vacation rentals
Explore 180 vacation rentals in Redmond
Nightly prices starting at
Redmond vacation rentals start at $42 CAD per night before taxes and fees
Verified guest reviews
Over 14,450 verified reviews to help you choose
Family-friendly vacation rentals
110 properties offer extra space and kid-friendly amenities
Pet-friendly vacation rentals
Find 70 rentals that welcome pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Wifi availability
180 of Redmond vacation rentals include wifi access
Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Redmond rentals
4.9 Average rating
Redmond stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated vacation rentals in Redmond
Guests agree: these stays are highly rated for location, cleanliness, and more.
Cozy Downtown Redmond Cottage
Welcome to our cozy Redmond cottage, located in the heart of downtown! Enjoy walking to local breweries, restaurants, and shops, all just steps away. This inviting space offers a perfect blend of comfort and convenience, ideal for couples or solo travelers. Unwind in the cozy living area after a day exploring Central Oregon. Experience the best of Redmond right outside your door! Conveniently close to: 15 minutes to Smith Rock 25 minutes to Bend 8 minutes to Deschutes County Fair & Expo Center
HOT TUB, Eagle Crest Condo on Golf Course, DOGS OK
This beautiful condo is located in the desirable resort community of Eagle Crest which is home to three 18-hole golf courses, an 18-hole putting course, and miles of trails. There is a private hot tub on the back deck that backs up to the golf course, as well as a BBQ. There are 2 spacious upstairs bedrooms each with their own private attached bathroom and walk-in closets. Downstairs is a fully stocked kitchen, propane fireplace, and dining area/table. Come enjoy all Eagle Crest has to offer!
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.
Pointe of Blessing with hot tub and canyon views
Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God 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.
Bend Ranch Guesthouse on 20 acres
Enjoy our private/detached guesthouse and wake up surrounded by nature on a 20 acre property bordered by farms and views of the Sisters Mountains. Excellent WIFI. Featuring wedding venue, Sage & Honey Spa, tube/lifejacket rentals. On the 2nd floor, 1 king bed, 1 queen bed, queen sofa bed, Full kitchen, refrigerator, dishwasher, microwave, hot plate, toaster oven, Keuirg. 17min to downtown Bend, 12min to downtown Redmond/Airport, 35min to Mt. Bachelor, 30mins to Sisters, 10mins to Tumalo.
Close to Smith Rock, Mountain View, Country Charm
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 :)
The Little Red Chimney House - 3 BR 2 BA
Originally built in 1944, this is a wonderfully furnished bungalow with 3 queen bedrooms and 2 full bathrooms, which I completely renovated and remodeled. It is a stone's throw from Fred Meyers grocery store and Cascade Lakes Brewery, and within easy walking distance to downtown. This house is at the hub of Central Oregon and sits at the crossroads between Bend (14 miles), Prineville (20 miles), and Sisters (20 miles) and is 10 miles from Smith Rock and 2 miles from the Airport.
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.
1918 Bungalow | Modern Renovation•Walk to Downtown
Beautifully restored 1918 bungalow in the heart of Downtown Redmond. Walk to local brewpubs, coffee shops, and food carts. Just 17 miles to Bend. Enjoy luxe linens, plush towels, a soaking tub, and a fully equipped kitchen. Immaculate, cozy, and full of character—this historic gem blends comfort, style, and walkable charm for a memorable stay. Steps from local favorites—food, drinks, and downtown vibes! Perfect base for exploring Smith Rock, and Central Oregon beauty!
Tin Can Ranch
Welcome to Tin Can Ranch! Kick your legs up and enjoy the sunset at Tin Can Ranch where your worries drop away like the leaves in Autumn! Our cozy Vintage Yellowstone "Tin Can" camper is nestled in it's own corner of our 5 acre property located in Terrebonne, OR just a 10 minute drive from Smith Rock State Park and within an hour of the very best outdoor adventures in Central Oregon! Next to the camper is the shower house/bathroom with an outdoor washing sink.
3bdrm Chalet + Hot Tub in Eagle Crest
Welcome! Come enjoy and relax in our rustic chalet. Unwind on the back deck while barbecuing, drinking a cup of coffee, or enjoying our private hot tub. Our chalet offers sports passes to all three sports complexes that include indoor/outdoor pools and tennis courts, spas and saunas, play grounds, BBQ areas, horse shoes, volley ball courts and much more. Enjoy golf, mini golf, enjoy nearby hikes and rivers. The perfect place for a family get away!
Modern Downtown Cottage near Outdoor Adventure
Nestled in the heart of Downtown Redmond, this beautifully designed cottage offers the perfect blend of convenience and comfort. You'll find yourself within walking distance of charming coffee shops and restaurants, and just 14 minutes away from the breathtaking Smith Rock. The Redmond Airport is less than 10 minutes away, and if you're planning a visit to Bend, you can be downtown or floating on the Deschutes River in under 20 minutes.
Popular amenities for Redmond vacation rentals
Stay near Redmond's top sights
Other great vacation rentals in Redmond
Spacious downtown pad - billiards/ping pong/sauna
Cascade View Suite · Balcony · Smith Rock
High-Desert Basecamp
Cozy Three Story Lookout Tower
Luxury Eagle Crest Chalet + Arcade | 3BRD
3BR home with yard, patio, WiFi, fireplace
"Little Pine Cabin" attached to my home.
Cozy 3 bdrm + loft Eagle Crest Chalet w/ Hot Tub!
When is the best time to visit Redmond?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $174 CAD | $160 CAD | $164 CAD | $173 CAD | $181 CAD | $203 CAD | $209 CAD | $202 CAD | $166 CAD | $160 CAD | $153 CAD | $163 CAD |
| Avg. temp | 2 °C | 3 °C | 5 °C | 8 °C | 12 °C | 16 °C | 20 °C | 19 °C | 15 °C | 9 °C | 4 °C | 0 °C |
Frequently Asked Questions
What are the best places to stay in Redmond?
Redmond has welcoming neighborhoods and plenty of vacation rentals near local parks, downtown shops, and family-friendly attractions. Consider staying around the historic downtown area to easily explore dining, events, and outdoor spaces.
What are the best things to do in Redmond with kids?
Families often explore community parks, splash pads, and interactive museums, or enjoy outdoor activities at nearby nature areas. The region has play spaces and seasonal events that are frequently suggested for children.
What are some of the best things to do in Redmond?
Redmond has scenic parks, river trails, boutique shops in the historic downtown, and nearby lava caves for those interested in geology. Visitors frequently enjoy local breweries, walkways, and art installations.
How is the weather in Redmond?
Redmond experiences dry, sunny summers with afternoons near 88°F (31°C), and winters around 23–44°F (-5–7°C) with occasional snowfall. Light rainfall is typical, so layers and sturdy shoes make exploring comfortable year-round.
When is the best time to visit Redmond?
Summer and early fall are often recommended for warm weather, festivals, and outdoor adventures. In spring, blooming wildflowers and milder temperatures draw visitors to trails and public spaces.
What are the best places to visit in Redmond?
Explore the historic downtown, stroll through city parks, and learn about local history at the nearby museum. Lava tube caves and public art also draw visitors seeking unique experiences.
What are some hiking trails in Redmond?
Redmond has riverfront paths, forested trails, and scenic routes through volcanic landscapes. Community parks and nature preserves frequently provide easy-to-access hiking opportunities for various experience levels.
What are some family activities we can do in Redmond?
Enjoy playgrounds, local splash pads, interactive museum exhibits, and outdoor picnics at city parks. Seasonal festivals and family-focused events are frequently suggested for visitors with children.
What are some of the best day trip ideas from Redmond?
Visitors often plan trips to explore the Cascade Mountains, volcanic parks, and scenic lakes near Redmond. Day excursions to neighboring towns with art galleries, outdoor markets, and historic sites are also popular.
Are there any pet friendly accommodations available in Redmond?
Many vacation rentals in Redmond welcome pets, especially in neighborhoods near public parks and walking trails. Check individual listings for pet policies and amenities suited to your companion.
What are some local tips for visiting Redmond?
Wear layers, as weather shifts between dry heat and cool evenings, and sturdy shoes are helpful for exploring rough terrain or lava caves. Locals often recommend checking community calendars for events and farmer’s markets.
What is Redmond known for?
Redmond is known for its high desert landscape, river access, and proximity to volcanic formations. The city enjoys a blend of outdoor recreation, community events, and local craft culture.
What are the best hidden gems to explore in Redmond?
Redmond has small art studios, locally owned cafes, and lesser-known trails winding through unique geological features. Quiet parks and community gardens also invite visitors to relax or explore off the main paths.
What are the best foods to try in Redmond?
Redmond has locally raised beef, fresh produce, and craft brews, reflecting Central Oregon's agricultural roots. Huckleberry treats, ranch-inspired plates, and hearty breakfasts featuring local ingredients are often recommended by visitors and residents.
What should I bring for a trip to Redmond?
Pack layers, sunscreen, a hat for sun protection, and sturdy shoes for exploring trails or volcanic areas. A reusable water bottle, jacket for cool evenings, and outdoor gear add comfort to your visit.
What is the nightlife in Redmond like?
Redmond’s nightlife centers around casual pubs, live music venues, and local breweries. The historic downtown has gathering spots for food, drinks, and occasional performances in an inviting atmosphere.
What are the most popular events or festivals in Redmond?
Redmond hosts a summer rodeo, seasonal craft fairs, and community celebrations during holidays like the Fourth of July. Local music festivals and park events are also frequently suggested throughout the warmer months.
Are there family friendly vacation rentals in Redmond?
Redmond has many family-friendly vacation rentals, including homes near parks, splash pads, and attractions. These stays often provide amenities like play spaces and extra bedrooms for group comfort.