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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Guest favourite
An A-frame cabin is surrounded by tall pine trees, with a hot tub located on a stone patio. Soft lighting illuminates the cabin's exterior, and a balcony is visible above the entrance. A white chair is placed beside the hot tub, creating a relaxing retreat.
Cabin in La Pine
4.92 out of 5 average rating, 424 reviews

A-Frame cabin • hot tub • near Bend • Crater Lake

This cozy and unique A-frame cabin sits on 1+ private acres in the Deschutes Forest. Relax here with wooded pines, hot tub jacuzzi, soaking bathtub, 80" home theater projector, modern amenities, and beautiful forest views. Close to the city of Bend and all the outdoor activities Central Oregon has to offer. Proximity to the best hiking trails, mountain bike trails, hot springs, Deschutes River, Mt Bachelor ski resort, Cascade Lakes highway, Smith Rock State Park, and Crater Lake National Park.

Top Guest favourite
A relaxing outdoor space features a hot tub with gentle blue lighting, surrounded by a paved patio. A fire pit with seating is visible, along with a cozy lounge area, creating an inviting atmosphere for gatherings or quiet evenings.
Home in La Pine
4.98 out of 5 average rating, 129 reviews

The Blue House in La Pine | Hot Tub | 2 King Beds

Nestled in the heart of nature, the Blue House offers you a perfect blend of forest charm & modern comforts. You can relax and unwind in the 4-6 person hot tub. Enjoy the soaring, vaulted wall of windows that bring nature to you. This modern, newly constructed 2300 sf. home is centrally located in Oregon to enjoy all that Oregon has to offer; amazing lakes, great food, close to Bend & all outdoor activities. This home features 2 King sized beds, 1 Queen bed & 1 single bed with luxury linens.

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
4.82 out of 5 average rating, 129 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
A four-poster queen bed is positioned against a rustic wooden wall. Soft white fabrics drape elegantly, creating a serene focal point. A cozy seating area is visible nearby, along with access to a private entrance through the door.
Barn in La Pine
4.99 out of 5 average rating, 157 reviews

Romantic Getaway at the Tree Farm - w/ Starlink

Nestled between Crater Lake National Park & Bend, our modern, rustic-bohemian barn sits on the outskirts of La Pine, Oregon, tucked within a serene one-acre grove of pine trees. Here in the foothills of the Oregon Cascades, you'll find peaceful days & star-filled nights—an ideal escape for individuals, couples, or small groups looking to explore our volcanic wonderland. The space includes a cozy private backyard, perfect for reading, stargazing under the night sky, or simply unwinding.

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, 238 reviews

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

If you’re heading to Central Oregon to hike, ski, or explore, our cabin is the perfect spot for you. Tucked away on a quiet acre in Three Rivers, we offer a cozy, eco-friendly basecamp for your 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 touches. 30 min to Bend and Mt. Bachelor, 15 min to Sunriver — and far from the noise.

Top Guest favourite
A rustic cabin constructed from logs is shown, featuring a sloped roof and large windows that allow natural light to enter. A covered porch is supported by round wooden posts, with rocking chairs arranged thoughtfully on the porch for relaxation.
Cabin in Crescent
4.93 out of 5 average rating, 206 reviews

Grampie's Cabin

The family created Grampie’s Cabin on 2 acres in Central Oregon, just a few miles from Crescent Lake and a short distance from Willamette Pass Ski Resort. Miles of trails to walk or atv. Our hope is your family/friends will make wonderful memories. We do allow dogs but you must declare them and pay a $25. cleaning fee for the pets. Maximum 2 dogs please and they are NOT allowed on any furniture. Please respect this so we can continue to allow your fur babies.

Top Guest favourite
A modern two-story Bardominium is displayed, featuring a spacious exterior with a white facade and wooden accents. Two large black garage doors are positioned at the front, complemented by tall pine trees in the background and a clear blue sky above.
Home in Crescent
4.99 out of 5 average rating, 140 reviews

Crescent Butte Barndominium with Disc Golf

Take advantage of low Spring prices! Our 2 bed, 2 bath Bardominium is filled with extras including access to the Gilchrist State Forest, private 9 hole disc golf course and a Level 2 EV Charger. Enjoy the view of Diamond Peak, hiking or SxS in the 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 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
4.94 out of 5 average rating, 192 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

Guest favourite
Home in Crescent
4.97 out of 5 average rating, 119 reviews

Cozy and Private cabin in the woods!

Take it easy at this unique and tranquil getaway. This cute little gem sits just outside Diamond Peaks subdivision in beautiful Crescent Lake. Farm house feel. Unlimited outdoor activities for all seasons! Located on Royce Mountain loop groomed trail. Close to Crescent and Odell Lake and 10 minutes from Willamette ski area. During winter months a 4 wheel drive vehicle is recommended.

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, 869 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

Top Guest favourite
Tiny home in Springfield
4.96 out of 5 average rating, 369 reviews

Creekside Cottage with Hot Tub

Escape to a private creekside studio cottage for up to 4 guests. This serene hideaway features a covered hot tub, an expansive deck with a BBQ, and a unique outdoor shower. Perfect for a romantic getaway or small family adventure near the McKenzie River, it offers a dedicated workspace, high-speed Wi-Fi, and a fully equipped kitchen. Enjoy peaceful seclusion with modern comforts.

Top Guest favourite
Guest suite in La Pine
4.96 out of 5 average rating, 287 reviews

Guest suite | Hot tub & sauna Cabin in the Woods

Private guest suite in our newly built home, just steps from a cabin-style spa with a hot tub and infrared sauna. Relax in the peaceful forested backyard, enjoy high-speed 300 Mbps Wi-Fi, and watch starry skies. A campfire to unwind, a sunset to inspire, and the Milky Way framed by towering Ponderosa pines — this place is the perfect blend of modern comfort and nature’s beauty.

Popular amenities for Diamond Peak holiday rentals

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