Vacation rentals in Diamond Peak

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Top-rated vacation rentals in Diamond Peak

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Guest favorite

Cabin in Douglas County

4.94 out of 5 average rating, 597 reviews

North Umpqua River King Cabin 15 Near Crater Lake

Rustic Mountain Cabins - Glamping! Our charming King Cabins are perfectly located along the North Umpqua River in the Umpqua National Forest. This region of the Oregon Cascades is commonly referred to as "Oregon's Emerald-Jewel Gateway" to Crater Lake. We are centrally located to the North Umpqua Trail, with easy drives to many trailheads, waterfalls & the Umpqua Hot Springs. The King Cabins have a King bed, and a loft w/ double bed. The shared bath/shower house is steps away from the cabins.

Feb 5 – 12

G$25,405 GYD per night

Guest favorite

Cabin in Douglas County

4.98 out of 5 average rating, 375 reviews

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!

Dec 21 – 28

G$39,943 GYD per night

Guest favorite

Home in Gilchrist

4.96 out of 5 average rating, 125 reviews

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!

Oct 27 – Nov 3

G$26,520 GYD per night

Guest favorite

Cabin in La Pine

4.95 out of 5 average rating, 200 reviews

Cozy Forest Cabin w/ Sauna & Hot Tub!

Our cozy cabin is an excellent getaway for anyone who just wants to be surrounded by everything that Central Oregon has to offer. With the National Forest and the La Pine State park just a few minutes away, there are options for hiking, biking, swimming, fishing, kayaking, paddle boarding or ATV rides. During the winter season, activities such as snowboarding, skiing, sledding, and snow mobile rides are only within 40 minutes away at Mt. Bachelor. City life in Bend is only 30 min away.

Nov 4 – 11

G$35,194 GYD per night

Guest favorite

Cabin in Crescent

4.96 out of 5 average rating, 172 reviews

Mountain Retreat

Our family’s cabin in the woods. Hiking trails right out the front door!! Crescent lake is 5 mins away. Willamette pass ski is 15 min s away Umpquah hot springs and crater lake both a little more than an hours drive 4 kayaks available to use Salt creek falls .... super scary viewing height !! 15 min away Sleds available, PLEASE return them TO THE GARAGE after using them. We average 20 FEET of SNOW... we won’t find them till spring melt. General market/store is close by

Dec 9 – 16

G$38,235 GYD per night

Guest favorite

Guesthouse in Eugene

4.98 out of 5 average rating, 192 reviews

New 1 room 1,100 sq. ft. Guest House with views

Located in the South Hills of Eugene. Close to U of O with easy driving access to amenities. The garage guest house, sits on 3 wooded acres w/ south views to Creswell and winter views of the Three Sisters to the east. Built in 2020, the studio features a large walk in shower, full kitchen, and laundry amenities. Sleeps 6 (queen, double sleeper sofa and two twins) Parking for multiple cars if needed. Unwind in a peaceful, natural Oregon setting, we look forward to hosting you.

Sep 15 – 22

G$25,142 GYD per night

Guest favorite

Home in Crescent

4.94 out of 5 average rating, 313 reviews

Crescent Cabin by Lakes & Rivers

Enjoy the snow with your family during Spring Break! We are only 24 miles from Willamette Pass Ski Resort. The Norway Crescent Cabin is a 3 bedroom, 2 bathroom completely remodeled home in Crescent Oregon. Located 17 miles S. of La Pine off Hwy 97, it's still close to all those great Central Oregon activities, but without the high costs and loads of people. You will find the house comfortable, efficient and very reasonably priced for a great get-away. Read more for details.

Jan 4 – 11

G$22,645 GYD per night

Guest favorite

Cabin in Bend

4.99 out of 5 average rating, 429 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. 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 .

Mar 18 – 25

G$18,375 GYD per night

Guest favorite

Home in La Pine

4.95 out of 5 average rating, 510 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.

Feb 15 – 22

G$19,089 GYD per night

Guest favorite

Cabin in Oakridge

4.96 out of 5 average rating, 697 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

Apr 10 – 17

G$17,108 GYD per night

Guest favorite

Guesthouse in La Pine

4.94 out of 5 average rating, 107 reviews

Ponderosa Pines Bunkhouse - Dog friendly ADU

Bring your favorite person, your animals and have some fun! The Little Deschutes River is a short walk away down a dirt road. Come and enjoy outdoor recreation and quiet nights under the stars. After a good snowfally, you can snowshoe from the door into backcountry BLM land. Easy drive into Bend for some entertainment or the mountain ski slope for a day of shredding.

Nov 30 – Dec 7

G$15,278 GYD per night

Guest favorite

Cottage in Oakridge

4.96 out of 5 average rating, 319 reviews

River Song Cottage

Let the river sing you to sleep in this sweet and brand new little cottage. Our place is within easy walking distance to restaurants and stores for any supplies you may need when you hit the trails. Or, could just hang out here, cast a fly, launch a raft or enjoy the sounds and sights of the beautiful middle fork of the Willamette River, just being.

Apr 1 – 8

G$29,926 GYD per night