Holiday rentals in Diamond Peak

4.99 out of 5 average rating, 502 reviews

Cabin in Bend

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.

4.97 out of 5 average rating, 437 reviews

Cabin in Douglas County

Mountain Mama Lodge on the North Umpqua River

Nestled in the trees near the North Umpqua River, Mountain Mama Lodge is the perfect place to stay while exploring the Umpqua! We're about a 40min drive to the North entrance of Crater Lake Nat. Park, Lemolo & Diamond Lakes, and roughly 12 miles from Umpqua Hot Springs, Toketee Falls & Watson Falls. Local guides offer rafting trips down the North Umpqua River, and a favorite local swimming hole provides opportunities to cool off in the summer. The North Umpqua River is a fly fisher's paradise!

4.96 out of 5 average rating, 178 reviews

Guest suite in La Pine

ForestView Guest Suite + HotTub and Infrared Sauna

Private guest suite within our newly 2023-built home. Separate backyard area with Cabin In Deschutes Spa where the modern amenities meet the beauty of nature. Rest as calm as the doe and the fawns outside while staying seamlessly connected with high-speed 300 Mbps Wi-Fi. Savor the luxury of a hot tub and infrared sauna while watching as the squirrels teach their young to leap trees. This is life — a campfire to relax by, a sunset to inspire — in a home, guarded by pines framing the Milky Way.

4.93 out of 5 average rating, 204 reviews

Home in Gilchrist

Studio between Bend and Crater Lake on the water

Make some memories at this unique and family-friendly place. In the summer this 12 acre compound has numerous activities to keep you busy. Heated swimming pool, hot tub, tennis and basketball courts, badminton, volleyball bicycles, and lots of water toys…paddle boards, pedal boat, kayaks, and pontoon boats. Winter heated pool and hot tub, large fire pit and seasonal snow. Willamette pass 20 min. Wildlife very abundant, and a working lumber mill across the water. Sunsets are usually gorgeous!

5 out of 5 average rating, 151 reviews

Cabin in McKenzie Bridge

McKenzie Bridge River House near Sahalie Falls

Drive down a long private road, set off of the HWY, to find a riverfront cabin amidst the lush Willamette National Forest. As you wind through the driveway you will find a sanctuary for relaxation, recreation, and comfort. A trail from the back deck will lead you down to the bank of the emerald waters of the McKenzie River. The McKenzie River Trail parallels the property, and is accessed from the private road to the cabin. The property has a campground setting, with river and forest views.

4.9 out of 5 average rating, 305 reviews

Cabin in La Pine

Deschutes A-Frame Cabin close to Bend, Crater Lake

This cozy and unique A-frame cabin is settled in a private community within the Deschutes National Forest. Relax here with over an acre of pines, new hot tub, modern amenities, and beautiful view out back. 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, Deschutes River, Mt Bachelor ski resort, cascade lakes, hot springs, Smith Rock State Park, and Crater Lake National Park.

4.99 out of 5 average rating, 122 reviews

Barn in La Pine

Romantic Getaway at the Tree Farm - w/ Starlink

Located between Crater Lake National Park & Bend, in the quaint outskirts of La Pine, OR, you'll find our modern, rustic-bohemian Barn sitting amongst a 1- acre grove of pine trees. The quiet days and dark nights in the foothills of the Oregon Cascades are perfect for individuals, couples, or small groups exploring our volcanic wonderland. The Barn includes a small backyard for spending time in the fresh air reading, stargazing, or doing absolutely nothing.

4.91 out of 5 average rating, 135 reviews

Cabin in Bend

Eco cabin near Bend: hot tub, sauna, EV plug

Location Highlights • Peaceful acre in Three Rivers • 30 min to Bend and Mt. Bachelor • 15 min to Sunriver Relax • Soak in the hot tub under the stars • Rejuvenate in the barrel sauna • Unwind by the fire pit • Drift off in a hammock with your favorite book Inside • Warm knotty pine walls and juniper accents • Full kitchen, WiFi, 2 baths • Eco-conscious with bio-based flooring Book now and kickstart your Central Oregon adventure!

4.95 out of 5 average rating, 617 reviews

Home in La Pine

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.

4.84 out of 5 average rating, 117 reviews

Tiny home in Lane County

LUXE McKenzie River Tiny Haus | Whitewater Views!

Escape to a one-of-a-kind luxe tiny home overlooking the McKenzie River. Thoughtfully designed w/modern comforts, easy parking just off the Hwy. Immersed in nature, yet minutes from food, gas, shops. Relax by the firepit, BBQ, play cornhole or wander the private trail down to the rushing river's edge. Full Kitchen, Coffee, Cold AC, Hot Showers & HDTV for Streaming. Room to park Trailer, Boat, More.

4.97 out of 5 average rating, 154 reviews

Home in Oakridge

Panoramic View 2br on Hill in Uptown Oakridge

Enjoy maximum sunshine at this south facing 2 unit home atop a centrally located hill in uptown Oakridge. Our guests enjoy the location mostly for the maximum daylight and sunshine, the views of mountains to the south with sunrises and sunsets, and the ease of walking to uptown shops like Mane Street Coffee, Three Legged Crane Pub or the Corner Bar and Grill. Free Parking on site.

4.97 out of 5 average rating, 787 reviews

Cabin in Oakridge

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

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Other great holiday rentals in Diamond Peak

5 out of 5 average rating, 49 reviews

Home in Oakridge

Entire home in Oakridge, Oregon

SarahRating, 5 stars4 days ago

I highly recommend staying at Kelsey's home. She had everything you could possibly need and more. Wonderful location. Beautiful surroundings. Great communication from Kelsey if you had a question or needed anything. Also has a beautiful black kitty that likes to visit.

Holiday home in Crescent Lake

4.96 out of 5 average rating, 25 reviews

Newly Constructed Apartment in Prime Location!

BrandyRating, 5 stars3 months ago

Our stay was amazing. Luke made it very easy to settle in. Was very accommodating and responsive to all my questions. Thanks for sharing your beautiful home with us!

4.86 out of 5 average rating, 43 reviews

Cabin in Crescent

Crescent Lake Cabin

AimeeRating, 5 stars3 weeks ago

Our family of 5, plus elderly dog had a lovely long weekend stay at Crescent lake cabin. Our three kids (4,6,8) particularly enjoyed the shallow swim-able creek and the fire pit, and enjoyed meals on the deck with the sounds of the creek in the background. It was a quick drive to Crescent lake beaches and Salt creek falls should not be missed! The record player was fun, and the kitchen was well-equipped for the basic meals we cooked during our stay. There were plenty of bath and kitchen towels (though no beach towels which would be useful for the creek and nearby lakes). Our kids also appreciated the games (the marble run was a hit!) and we had a movie night - plenty of age appropriate choices in the DVD collection. Overall very pleased with our stay and would love to visit again!

5 out of 5 average rating, 53 reviews

Cabin in Crescent

Cascade Mountain Retreat

JocelynRating, 5 stars4 months ago

An amazing house!! We loved staying here. So clean and a very well-equipped kitchen. Such great linens and fluffy towels! Owner was very responsive when needed. Everything worked perfectly. Great location for skiing at Willamette Pass. Couldn’t be better!

5 out of 5 average rating, 20 reviews

Cottage in La Pine

A River Runs Thru It. Cottage, 8 Acres With Views!

ChelseaRating, 5 stars3 weeks ago

Absolutely stunning. Honestly the photos don’t even do it justice. I would come back in a heartbeat. Such a peaceful experience. The decor is phenomenal.

4.9 out of 5 average rating, 94 reviews

Cabin in Crescent lake

Pistachio

EricRating, 5 stars1 month ago

The Pistachio is everything you ever need and want for a quick getaway from the city. Peaceful and serene outdoor scene with a wonderful spacious interior of the Pistachio never felt to small but just right for myself and my partner. The hosts were attentive and provided excellent guidance both for check-in and check out or just general household questions. Would definitely stay at the Pistachio again.