Vacation rentals with a pool in Jefferson County

Chalet in Crooked River Ranch

A red timber-framed chalet is showcased, featuring a covered patio with picnic tables and chairs. The surrounding landscape includes landscaped areas and distant hills under a clear blue sky, creating an open and spacious environment.

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, 17 reviews

A cozy cabin is framed by surrounding greenery, showcasing a wraparound deck. Large windows reflect the colors of the sunset, enhancing the rustic wooden architecture. The tranquil landscape includes scattered trees and shrubs, contributing to the serene atmosphere of the setting.

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, 305 reviews

A spacious deck offers unobstructed views of the canyon and distant mountains during sunset. Comfortable outdoor seating is arranged around a central table, inviting relaxation while taking in the serene landscape. Warm hues light up the sky, creating a tranquil atmosphere.

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.

A seasonal swimming pool is surrounded by a spacious deck, with steps leading into the clear, inviting water. Dense pine trees provide a natural backdrop, and sport courts for activities are visible in the distance across a manicured lawn.

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, 472 reviews

An expansive deck overlooks the Deschutes River canyon, featuring a hot tub and several outdoor seating areas. The rugged landscape is characterized by rocky cliffs and sparse vegetation, leading to a serene view of the river winding through the canyon.

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.

A seasonal swimming pool is surrounded by a concrete deck, with a railing along one side. Lush green grass and tall trees are visible in the background, while a tennis court is situated outside the pool area.

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).

The outdoor splash pool is surrounded by a spacious deck featuring lounge chairs and a hammock. Natural grasses and shrubs frame the area, while a stone wall provides a backdrop. A clear sky with soft clouds enhances the serene atmosphere of the retreat.

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

An outdoor area features a splash pool and lounging spaces under shaded canopies. Natural vegetation surrounds the space, with a hammock draped nearby. A stone wall provides privacy, and the horizon displays a mix of greenery and sandy terrain beneath a dynamic sky.

Tent in Culver

Star Tent at Green Rock Retreat

Guest favorite

A row of rustic cabins is set against a natural backdrop, showcasing wooden exteriors and inviting porches. Each cabin features a distinct entrance, with picnic tables arranged on the deck. A gravel path leads through the surrounding shrubbery, offering a sense of tranquility.

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 favorite

A row of rustic cabins is set against a backdrop of hills, with a gravel path leading to a communal deck area. Each cabin features a welcoming porch and warm wooden finishes. Surrounding shrubbery adds to the natural scenery.

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!

The outdoor heated swimming pool is surrounded by a spacious deck, showcasing clear water. In the background, tall pine trees create a peaceful setting, with sport courts visible for tennis and other games.

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!

A heated outdoor pool is visible, surrounded by a spacious patio and lush greenery. Tall pine trees frame the scene, with tennis courts clearly seen in the background. The pool's clear water invites relaxation and leisure in a natural setting.