
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.

Near SmithRock pets ok private heated bungalow
close to smith rock. golf course, tennis court, store, 3 bars, 5 minutes away. ample parking. We live on 4 dusty acres, and are pet friendly, so although we pride ourselves on the cleaning and sanitizing we perform between guests we also ask if you are super picky please refrain from booking, this is definitely not a luxury hotel in the city. If there are any discrepancies upon arrival please let us know.. We try to keep our price the lowest in the area, and strive to attain that 5 star review.

Creekside Luxury @ Eaglecrest-Dog Friendly Escape!
Nestled next to a serene creek, our home in Eaglecrest Resort offers a tranquil escape like no other. In addition to our two bedrooms, two baths, and proximity to great breweries, you'll have the soothing sound of flowing water right at your porch. Immerse yourself in nature's symphony as you relax on the patio or take a leisurely stroll along the creek. Let the peaceful ambiance rejuvenate your senses and create lasting memories. Book now and experience the serenity of our creekside retreat.

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.

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 daylight basement apartment with dedicated entrance and parking, open concept living, laundry, bedroom and custom bath. Luxe accommodation just minutes from Smith Rock State Park. A covered deck with magnificent views will make you feel right at home. Start your day with a gorgeous sunrise over Smith Rock

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.

Stunning! Smith Rock • King Beds • Steam Shower
A wall of glass provides panoramic views of the iconic Smith Rock formation, creating a seamless connection between the indoor and outdoors. A sleek and sophisticated modern home perched on the rimrock and flooded with sunshine. King beds and a luxurious bathroom with steam shower. Includes Smith Rock Pass. *No parties or pets* (including support animals) please - this is a 'pet-free' home for guests with allergies. Trip insurance recommended if illness, weather or smoke may be an issue.

Mountain View Suite near Smith Rock - Fast Wi-Fi
FAST INTERNET. Quiet rural location a few miles from town on rimrock over a small canyon. Enjoy a wide view of the Cascades from a roomy studio apartment that is comfy and uncluttered. Features a big bathroom, walk-in shower, a small balcony, many windows, and a large walk-in closet. On request for additional $35 per stay: roll-away bed. Nearby attractions: 1) Smith Rock State Park-7 mi 2) Dry Canyon trail-1 mi 3) Redmond Airport-6 mi 4) Redmond-5 mi 5) Sisters-23 mi 6) Bend-22 min

IT'S A WEE HOUSE
Quiet, serene, warm and cozy. Relax in this cute little pet friendly WeeHouse with a wee loft. Located in the heart of Central Oregon just minutes from downtown Bend and the Redmond airport. You'll enjoy countryside views of Smith Rock and the valley below. Bask under 1000 year old Juniper trees. High Speed wifi, private bathroom and kitchenette. If this doesn't feel like a fit or is unavailable please check out our other options: "The Sunset Bungalow" and "The Sunrise Studio"

Downtown Redmond Retreat
Welcome to our charming retreat nestled in the heart of Downtown Redmond! Situated in a quit neighborhood and 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...

Blossom Cottage Studio
Keep it simple and take it easy at this peaceful and centrally-located, unique, cozy getaway. The Blossom Cottage Studio is located in a beautiful garden setting. ~The space~ • One Room Studio • 1 Bathroom • Full sized bed (additional cot if needed) •Kitchenette (Refrigerator w/small Freezer, Toaster Oven, Microwave, Blender, Kuerig, etc) •Short walk to the heart of downtown Redmond. The cottage is private and located on the back property of a Gift Boutique Shop and Bakery/Cafe.

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.

Larkspur Garden Guesthouse
Located in Bend's Midtown and with access to the Larkspur trail that leads to iconic Pilot Butte, this bright, newly built 450 sq. foot apartment balances cozy and modern elements to make your stay in Bend comfortable. Equipped with a full kitchen, a separate room with a queen bed, a deep, relaxing tub, a sofa that converts into a memory foam queen bed, a TV with access to Netflix, and a separate laundry room. Our space is a great option for 2 guests, but it can fit up to 4.
Popular amenities for Redmond holiday rentals
Other great holiday rentals in Redmond

Valleyview Studio

The Sunshine Loft

Ranch Cottage: Desert, Forest, Horses, Hot Tub

Eco cabin near Bend: sauna, hot tub, EV plug

Luxe 4BR/3BA • Smith Rock, 9 Peaks, Hot Tub, 10 Ac

Sixties Suite Spot

Brand New Downtown Redmond Private ADU on Canyon

The Quail Nest
When is the best time to visit Redmond?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $139 SGD | $144 SGD | $148 SGD | $140 SGD | $157 SGD | $171 SGD | $193 SGD | $186 SGD | $153 SGD | $153 SGD | $161 SGD | $157 SGD |
| 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.
Quick stats about holiday rentals in Redmond

Total holiday rentals
Explore 190 holiday rentals in Redmond

Verified guest reviews
Over 13,150 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
190 of Redmond holiday 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!
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