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Holiday houses in Diamond Peak

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Top-rated holiday rentals in Diamond Peak

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A kitchenette area is visible featuring a wall-mounted counter with two wooden stools. A teal cabinet is positioned beside a coffee maker, while a window provides natural light and a view of the surrounding trees.
Guesthouse in Eugene
4.98 out of 5 average rating, 127 reviews

Hillside Cabin Retreat

Escape to our tranquil guesthouse nestled in the woods, offering a private retreat just minutes from Eugene's city center & the University of Oregon. This cozy cabin features a well-equipped kitchenette, luxurious outdoor shower & spacious deck perfect for enjoying meals while observing local wildlife & sunsets. Unwind in the hammock & fall asleep to the sounds of nature. Conveniently located near Hayward Field & downtown Eugene, our guesthouse provides a unique blend of serenity & convenience.

Guest favourite
The A-frame cabin is framed by tall pine trees, showcasing a modern black exterior. Large windows reflect the surrounding forest, while a wooden deck serves as an entry point, inviting guests to explore the natural setting.
Cabin in La Pine
4.97 out of 5 average rating, 117 reviews

| Le Chalet | 1+ acre| Remodeled | Quiet |

Discover tranquility in our A-frame cabin nestled among the pines. A rustic haven where the scent of pine fills the air, inviting you to unwind on the porch. Inside, a cozy living space & quaint kitchen offer comfort. Retreat to the loft bedroom, where the soft glow of morning light through pine branches awaits. Whether a romantic escape or family adventure, this cabin is a sanctuary, a respite from the daily rush. Embrace simplicity, enjoy the peace & quiet, and enjoy all the nearby beauty.

Top Guest favourite
A charming tiny log cabin is nestled amidst tall evergreen trees, gently blanketed in snow. The cabin's sloped roof is thick with snow, creating a cozy appearance. A path through the white snow leads toward the cabin's entrance, inviting exploration in a serene winter landscape.
Cabin in Bend
4.99 out of 5 average rating, 540 reviews

Skyliners Getaway

Our tiny log cabin is a cozy getaway, close to hiking, mountain biking, and cross country skiing but only 10 miles from the amenities of Bend Oregon. It is a rustic place, with modern touches, like a gas range, refrigerator, and a gas fireplace. The bathroom is detached from the cabin - steps from the door. It is fully equipped with plumbing and a shower. Our place is perfect for people who love the outdoors with the comforts of home. No children under the age of 12 -- And alas, No Pets.

Superhost
A wooden cabin is nestled among tall trees, featuring a sloped metal roof and several skylights. A small set of stairs leads up to the entrance. The surrounding area is covered with a mix of gravel and natural earth, creating a rustic outdoor setting.
Guesthouse in Klamath County
4.81 out of 5 average rating, 122 reviews

Cozy Cabin in Crescent Lake

Newly upgraded Cabin in Crescent Lake. Very cozy one bed room with fully updated kitchen and appliances. This is one of two Cabins on the same 4 acre property. The other Cabin is also available for rent on Airbnb. Perfect for two but can accommodate up to four people. The Cabin is located by the highway 58, easy to access, and very close to multiple Lakes including Crescent, Odell, Waldo and Crater Lakes. Not to mention other various natural attractions including Willamette Pass Ski resort.

Top Guest favourite
Home in Oakridge
4.99 out of 5 average rating, 125 reviews

Mountain Peak Views from Hot Tub in Uptown 2 Bdr

Kick back and relax at this peaceful 2 bedroom on a hill in uptown Oakridge. Your side of this duplex features on site parking, 2 bedrooms, a fenced backyard, full washer and dryer, and a private hot tub on your back porch. The property is within walking distance of 3 Legged Crane Brewery (the pub), Morning Light Coffee, the Corner Bar, the post office, and the library. Great for a bike trip, hiking, frisbee golf, a visit to Willamette Pass, or Crater Lake! Free Parking on site!

Top Guest favourite
A modern studio features a spacious bed with crisp white linens, a wooden accent wall, and an electric fireplace below a wall-mounted television. A unique wood table sits atop an area rug, with plants adding a touch of greenery to the warm atmosphere.
Condo in Bend
4.98 out of 5 average rating, 283 reviews

Sunriver Studio with Pool and Hot Tub

This stylish studio in the heart of Sunriver is newly remodeled with a King bed. Seasonal pool and year round Hot Tub! Just a short walk to a brand new food truck lot with 7 trucks, indoor and outdoor seating and a bar. Fast WiFi, a new Samsung 50” tv signed into Netflix, Hulu, HBO Max and more. 25 minutes to Mt. Bachelor. 25 minutes to downtown Bend. Parking is just a few feet from your door. This super clean condo is perfect for all of your central Oregon adventures.

Top Guest favourite
A snowy slope is visible leading down to a cozy two-story Barndominium, surrounded by tall pine trees. Warm lights illuminate the exterior, creating a welcoming ambiance. A figure is seen sledding down the hill, showcasing a fun winter activity right outside the home.
Home in Crescent
4.99 out of 5 average rating, 126 reviews

Crescent Butte Barndominium with Disc Golf

Take advantage of low Spring prices! Our 2 bed, 2 bath Bardominium is filled with extras including a sledding hill, snowshoeing on the property, private 9 hole disc golf course and a Level 2 EV Charger. Enjoy the view of Diamond Peak, hiking in the Gilchrist State Forest right out the door. We are about 45 miles to the N. entrance of Crater Lake. The "Barn" is perfect for 2 couples, or families. Enjoy this upscale country setting.

Top Guest favourite
A single-story home is framed by tall trees in a natural setting. The entrance is approached by a set of steps leading to a small porch. Large windows allow for natural light, while the surrounding area features a grassy landscape.
Home in La Pine
4.95 out of 5 average rating, 689 reviews

Cozy Getaway in the Pines

Located between La Pine and Crescent in a very quiet and private neighborhood. The property sits on one acre and is easily accessible by a paved road. A fire pit is available for use (wood supplied). Come enjoy all Central Oregon has to offer: hiking, biking, fishing, hunting, skiing, you name it! Please contact me to discuss pets. Being a pet lover, I am likely in favor of them joining with a few agreed upon guidelines.

Guest favourite
A cottage entrance is framed by wooden steps and surrounded by landscaped stones. Two white Adirondack chairs with striped cushions are positioned on either side of a fire pit, which features a rustic wood arrangement. Soft lighting strands add a welcoming glow.
Home in Lane County
4.94 out of 5 average rating, 133 reviews

The Little Lodge

The Little Lodge is a 2024 remodeled mid-century cottage. Centrally located around restaurants, golf, hiking, waterfalls, fishing, and the McKenzie River. This mountain style home is perfect for an individual, or two. A private trail from the back deck leads down to the emerald waters of the McKenzie River. Detailed craftsmanship intended to offer the cozy mountain feel, and outdoor living for scenic relaxation.

Guest favourite
A private outdoor area features a hot tub surrounded by string lights, creating a cozy ambiance. A wooden table displays a bottle of sparkling wine with two glasses and a small potted plant, inviting relaxation and enjoyment in nature.
Cabin in Bend
4.92 out of 5 average rating, 202 reviews

Eco cabin near Bend: sauna, spa, king bed, EV plug

Tucked away on a quiet acre in Three Rivers, our cabin is a cozy, eco-friendly basecamp for Central Oregon adventures. Soak in the hot tub after a day on the trails, warm up in the barrel sauna, or gather by the fire pit under the stars. Inside, you’ll find knotty pine, a full kitchen, WiFi, and thoughtful eco-friendly touches. 30 min to Bend and Mt. Bachelor, 15 min to Sunriver — and far from the noise.

Top Guest favourite
A spacious living area showcases large windows that provide panoramic views of the surrounding mountains. A stone fireplace stands as a focal point, complemented by comfortable leather sofas and a wooden coffee table. Natural light fills the room, enhancing the inviting wooden interior.
Cabin in Crescent
4.93 out of 5 average rating, 182 reviews

Luxury Chalet: Views, Hot Tub and Fireside Comfort

Escape to our luxurious chalet on 3+ wooded acres with panoramic views. Enjoy a fully equipped kitchen, high-speed internet, hot tub, BBQ, AC, fireplaces, TV with streaming, washer/dryer, and pet-friendly policy. Near Crater Lake, indulge in summer lakes and winter ski resorts. Experience ultimate relaxation in our serene forest retreat with top-tier amenities and unbeatable access to outdoor adventures

Top Guest favourite
A rustic cabin with wood siding and a sloped wooden staircase is nestled among towering trees. Large windows provide natural light, and the surrounding area features a mix of forest vegetation and dirt pathways.
Cabin in Oakridge
4.97 out of 5 average rating, 838 reviews

Lone Wolf Cabin, pet friendly

Lone Wolf Cabin is situated on a gated road in a forest setting. It is the only residence on the road. It is about 2 miles from both Oakridge and Westfir which makes it convenient for mountain bike riding, hiking, golfing and dining out. There are both Forest Service Trails and game trails near the cabin. The cabin is rustic with modern conveniences. Weekly discount is $500.00

Popular amenities for Diamond Peak holiday rentals

  1. Airbnb
  2. United States
  3. Oregon
  4. Lane County
  5. Diamond Peak