Holiday rentals in Redmond
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Quick stats about holiday rentals in Redmond
Total holiday rentals
Explore 180 holiday rentals in Redmond
Nightly prices starting at
Redmond holiday rentals start at $38 SGD per night before taxes and fees
Verified guest reviews
Over 14,450 verified reviews to help you choose
Family-friendly holiday rentals
110 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 70 rentals that welcome pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Wifi availability
180 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!
Top-rated holiday rentals in Redmond
Guests agree: these stays are highly rated for location, cleanliness and more.
Dog friendly Home near parks and Dry Canyon
Book your stay today and experience all the comforts of home, with the added bonus of a fantastic location within walking distance to local parks. Located in a quiet neighborhood, it provides a peaceful and tranquil atmosphere. Enjoy a large fenced yard with mature trees, perfect for barbecues and outdoor activities or star gazing in the hammock. The beginning of Dry Canyon trail is only a mile away for walking, running or taking the family for a bike ride. Close to local businesses and dining.
ValueFamilyAccess
4.96 out of 5 average rating, 147 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.
LocationValueCondition
4.84 out of 5 average rating, 718 reviews
Quiet Eagle Crest Townhouse w/ Access to Amenities
Enjoy all that Central OR has to offer in this quiet, end-unit townhouse. Located in Eagle Crest Resort, a 1700-acre resort with one spa, three sports centers, five pools, and three full year-round golf courses, it is the ideal location to enjoy Central OR. This 1400sq ft single-level townhome features a great room with soaring ceilings, walls of windows, a fully stocked kitchen, and plenty of gathering spaces. Perfect for a romantic getaway, fun family weekend, or adventure-filled vacation.
ValueLocationComfort
4.91 out of 5 average rating, 159 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 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
ValueLocationHeating
4.97 out of 5 average rating, 593 reviews
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.
FamilyValueCleanliness
4.97 out of 5 average rating, 398 reviews
Bend Country 4 BR/3 Bth, Amazing 9 Mt View, 9 acre
Plan your vacation getaway and escape the destination resorts at our quiet & peaceful lodge home retreat on 9 private acres just north of Bend, "in the country but not far away"; only 10 min. to restaurants & stores if you need anything. Relax while gazing at the amazing 9 Cascade Mts and overlooking a bend of the legendary Deschutes River. Enjoy some of the many Central OR area activities, Skiing, Golfing, Fishing, Hiking, Rock Climbing, Biking, local Wineries & Micro Breweries, & more.
FamilyValueKitchen
4.97 out of 5 average rating, 134 reviews
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.
ValueLocationCheckout
4.92 out of 5 average rating, 182 reviews
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.
LocationFamilyQuiet
4.87 out of 5 average rating, 517 reviews
Greenside 3 BdRm + Hot Tub Chalet in Eagle Crest
Welcome! Come to relax or adventure while staying at our rustic chalet. Located in a prime location at the end of the street, this chalet has everything you will need to enjoy your time away from home. Get cozy inside by the fire, or enjoy the sunrise and sunset on the secluded deck overlooking the 14th green and Cascade Range. Adventurers can venture out to enjoy the sports center, award winning golf courses, and more! The Eagle Crest Resort has fun for the whole family.
FamilyValueBiking
4.95 out of 5 average rating, 208 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.
FamilyLocationLaundry
4.96 out of 5 average rating, 744 reviews
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!
LocationValueAccuracy
4.92 out of 5 average rating, 661 reviews
Cozy 3 bdrm + loft Eagle Crest Chalet w/ Hot Tub!
Welcome to our Chalet in the Eagle Crest Resort! You are guaranteed to feel like you are on vacation the minute you walk in. This 3 bedroom + loft can sleep 8 guests and comes with washer/dryer, WiFi, and desks in the loft. Relax in the space indoors or out, with the outdoor patio, hot tub, BBQ, and golf course views. There is so much to see and do on the resort property or you can grab a blanket, sit by the fire and do absolutely nothing at all!
LocationValueBack garden
4.98 out of 5 average rating, 289 reviewsPopular amenities for Redmond holiday rentals
Stay near Redmond's top sights
Other great holiday rentals in Redmond
Eagle Crest Chalet with HOT TUB | On Golf Course!
LocationFamilyBathroom
4.98 out of 5 average rating, 116 reviews
Smith Rock Oasis w/ Hot Tub Steps to the Park
ValueLocationAmenities
4.94 out of 5 average rating, 186 reviews
Spacious downtown pad - billiards/ping pong/sauna
FamilyValuePool
4.92 out of 5 average rating, 259 reviews
Cozy Downtown Redmond Cottage
ValueLocationGetting around
4.92 out of 5 average rating, 132 reviews
Large Group Comfort - 7 Separated Sleeping Areas!
ValueFamilyCheck-in
4.93 out of 5 average rating, 192 reviews
The Downtown Guesthouse
FamilyValueDecor
4.84 out of 5 average rating, 286 reviews
Sagebrush Cabins - Modern elegance and epic views!
LocationValueView
4.91 out of 5 average rating, 129 reviews
Smith Rock Gardens
LocationValueCheckout
4.98 out of 5 average rating, 296 reviewsWhen is the best time to visit Redmond?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $160 SGD | $147 SGD | $151 SGD | $158 SGD | $166 SGD | $186 SGD | $191 SGD | $185 SGD | $152 SGD | $147 SGD | $140 SGD | $149 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.