Holiday rentals with a pool in Jefferson County

Chalet in Crooked River Ranch

4.87 out of 5 average rating, 52 reviews

Classic Timber Framed Chalet

Our Classic Timber Framed Chalet the perfect place to call your home away from home. A main floor master bedroom with king bed & separate sleeping loft are perfect for families or groups. The full kitchen makes the Chalet the complete package for your next vacation rental. Pet Friendly (Pet fee required, max 2 pets) And the views! Take in the expansive views across the 14th hole of the CRR Golf Course and marvel at the towering canyon walls & mountains in the background from your private deck.

5 out of 5 average rating, 19 reviews

Cabin in Terrebonne

The Rim House, Timeless & Serene

High desert beauty is on full display, no matter the season. Deer, rabbits, quail cross just outside your windows, eagles soar overhead, and yipping coyote echo across the canyon at night. This gem of a getaway is not new to visitors to Terrebonne and Crooked River Ranch. It’s been a guest favorite for over ten years- in March 2025 we purchased the home and are pleased to continue sharing it's unique qualities and location… and to live up to former host Michelle’s high standards of hospitality!

4.97 out of 5 average rating, 306 reviews

Home in Terrebonne

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.

4.8 out of 5 average rating, 15 reviews

Creekside Studio Cabin at Lake Creek Lodge

Cabin 7 at Lake Creek Lodge is the coziest of them all, with a fireplace literally at the foot of your queen bed. Located just downstream from the main Lodge in a wooded area that is perfect for watching the wildlife, this cabin has a kitchenette and private bath with everything you'll need for a comfy stay. Bring your pooch to hike the Metolius Basin trails, fly fish our private pond, swim in our seasonal pool and enjoy fun evenings in Lake Creek Lodge's restaurant and bar.

4.96 out of 5 average rating, 474 reviews

Home in Terrebonne

Canyon House, Crooked River Ranch

Canyon House sits on the edge of the Deschutes River canyon and has a beautiful and scenic view of 11 mountains and peaks. Your home is a 2 bedroom and 2 bath 1450 sf manufactured home. It is attached to ours and Donna and I live on site family. Your privacy is my first rule and quiet is my second. Yet, you may see me watering plants or checking on the Spa. We are open for a 1 night minimum. Checkout time is strict to allow for cleaning and sanitizing on same day check ins.

5 out of 5 average rating, 3 reviews

Two Bedroom Creekside Cabin at Lake Creek Lodge

These cabins are a favorite amongst our guests that come back year after year. Located adjacent to Lake Creek, perfect for watching the wildlife, these cabins have a living room full kitchen, 2 bedrooms (1 queen bed & 2 twin beds) and a private bath with everything you'll need for a comfy stay. Bring your pooch to hike the Metolius Basin trails, fly fish our private pond, swim in our seasonal pool & enjoy fun evenings in Lake Creek Lodge's restaurant and bar (seasonal).

Tent in Culver

Moon Tent at Green Rock Retreat

Escape to a 50-acre off-grid yoga sanctuary on the rim of Crooked River Canyon. Enjoy yoga next to the splash pool. Feel the sun kiss your skin in your private outdoor shower. Watch the crooked river from the 500-foot-tall overlook. Listen to the wind rustle the canvas of your safari tent as you unplug for the first time in a long time. The tent offers off-grid blissful living designed for healing and rejuvenation, and is a part of Green Rock Retreat.

5 out of 5 average rating, 5 reviews

Tent in Culver

Star Tent at Green Rock Retreat

Guest favourite

Cabin in Crooked River Ranch

4.93 out of 5 average rating, 115 reviews

Classic Cozy Cabin with Awe-inspiring Views

Come enjoy rustic relaxation in our Classic Cozy Cabin. It's 208sq ft of cozy comfort in the breathtaking Crooked River Gorge. The private cabin is equipped with a private bathroom, kitchenette, wifi, cable TV, private deck, and just enough leg room to rest, relax and unwind after a day of adventure in beautiful Central Oregon! And the cabin is pet friendly! (Pet fee required, max 2 pets). It's a great place to kick off your boots and stay awhile!

Guest favourite

Cabin in Crooked River Ranch

4.88 out of 5 average rating, 80 reviews

Classic Cozy Cabin with Awe-inspiring Views

Come enjoy rustic relaxation in our Classic Cozy Cabin. It's 208sq ft of cozy comfort in the breathtaking Crooked River Gorge. The private cabin is equipped with a private bathroom, kitchenette, wifi, cable TV, private deck, and just enough leg room to reset, relax and unwind after a day of adventure in beautiful Central Oregon! And the cabin is pet friendly! (Pet Fee Required, 2 pets max) It's a great place to kick off your boots and stay awhile!

Three Bedroom Creekside Cabin at Lake Creek Lodge

Original to the 1920’s, this cabin type is situated on the south side of the Main Lodge with a beautiful view of Lake Creek. This cabin type has 3 bedrooms (with either 2 queen beds & 2 twin beds or 1 queen bed & 4 twin beds subject to availability), 2 baths, a fully appointed kitchen. Many have fireplaces or woodstoves in the living area but are subject to availability. Enjoy all of the amenities at Lake Creek Lodge while staying with us!