House holiday rentals in Redmond

4.98 out of 5 average rating, 912 reviews

Cozy Three Story Lookout Tower

Thank you for your interest in The Cozy Lookout Tower! Our unique vacation home is really a destination location rather than just a place to stay while you explore the area. Many of our guests are repeat guests that use our home as a place to recharge, relax, cook, read, talk, play games and connect with that special someone. There are some lovely hikes in the area, we encourage you to bring your dog and enjoy the beautiful surroundings by taking some hikes then returning for a soak in the tub!

4.83 out of 5 average rating, 635 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.

4.99 out of 5 average rating, 240 reviews

Smith Rock Gardens

You'll enjoy the main house with the best views of Smith Rock and the Cascade mountains. Smith Rock State Park is literally across the street. A great location for outdoor activities at the park or in the region. Hike, climb, bike, walk or jog around the park. Sip tea inside and watch the animals. Perfect for artist and photographers. Relax on the deck or enjoy a sunset BBQ with gorgeous views. Owners live in adjoining unit. Separate entrance. Instagram: @smithrockgardens DCCA Tax# 1784

4.98 out of 5 average rating, 298 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.

4.99 out of 5 average rating, 271 reviews

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.

4.87 out of 5 average rating, 436 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.

4.94 out of 5 average rating, 220 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.

4.96 out of 5 average rating, 680 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.

4.97 out of 5 average rating, 271 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.

4.94 out of 5 average rating, 159 reviews

Fallen Snag Lodge next to Smith Rock State Park

One mile from Smith Rock State Park & 30 minutes from Bend, Fallen Snag Lodge will be your very own private nature preserve. A wrap around deck faces the Marsupial rock formations & Crooked river, with lounge chairs set to view hawks, turkey vultures & eagles during the day & for stargazing at night. Ideal for couples or a family wanting to get away from it all in a beautifully appointed, comfortable lodge set in central Oregon's magnificent high desert landscape.

4.96 out of 5 average rating, 186 reviews

Smith Rock Hideout - Cascade mountain views

Just 8 minutes to Smith Rock, the Hideout is a cozy retreat for climbers, hikers, trail runners, digital nomads, and anyone wanting to relax and explore the beauty of Central Oregon. Take in the views of the Cascade mountains and farmland beyond while relaxing on the covered porch. The Hideout is my personal retreat. While away, I’m happy to share it with outdoor enthusiasts who enjoy creature comforts after a day of getting after it outdoors.