Holiday Rentals in Southern Oregon
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A rugged coastline with a clear blue sky and a visible contrail.

Southern Oregon Holiday Rentals

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your current months are November, 2026 and December, 2026.

November 2026

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December 2026

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Our top choices for Southern Oregon holiday rentals

A campfire, wooden chairs, and a bench in a forested area with a view of a bridge.

A rustic wooden building with a signboard for 'Bock's Restaurant' indicating it's open.

A staircase with wooden steps and handrails, surrounded by walls covered with vintage newspaper clippings.

A wooden-paneled room with a sectional sofa, a dining table, and a ceiling fan.

1. Union Creek Resort

Union Creek Resort

3.0 star property

Prospect

8.0 out of 10, Very good, (1,120 reviews)

8.0/10

Very good

(1,120 reviews)

"Nice area with lots of hiking access, nice for a weekend getaway"

Brett

The price is S$111

S$111

includes taxes & fees

10 Nov - 11 Nov

Union Creek Resort

A cabin surrounded by snow-covered trees and a small pond.

A modern outdoor deck with a glass enclosure, wooden furniture, and a view of a forested area.

A kitchen with dark wood cabinets, a granite countertop, and a gas stove. There is a large window with blinds, a microwave, and a sink.

A rustic cabin surrounded by tall trees and dense vegetation.

2. Crater Lake Resort

Crater Lake Resort

3.0 star property

Chiloquin

8.4 out of 10, Very good, (608 reviews)

8.4/10

Very good

(608 reviews)

"Place was fantastic. And great location to crater lake. We loved everything about the resort"

Allan

The price is S$156

S$156

includes taxes & fees

1 Dec - 2 Dec

Crater Lake Resort

A clear view of a lake with a mountain in the background, a dock, and a chair on a deck.

A restaurant with large windows offering a view of a lake and mountains.

A wooden interior with a bar area, leather seating, and large windows offering a view.

A lodge surrounded by dense forest and a calm lake.

3. Rocky Point Resort

Rocky Point Resort

2.5 star property

Klamath Falls

8.2 out of 10, Very good, (520 reviews)

8.2/10

Very good

(520 reviews)

"We enjoyed staying there Good location"

Siranush

The price is S$124

S$124

includes taxes & fees

10 Nov - 11 Nov

Rocky Point Resort

A modern kitchen with a built-in microwave, a coffee maker, and a large flat-screen TV mounted on the wall.

A brick building with a sign reading '111 Main' and a large sign for 'The George.'

A bedroom with a bed, a ceiling fan, a bedside table, a lamp, a window, and a door.

A living room with a sectional sofa, a glass coffee table, a patterned rug, and a dining area with a table and chairs.

4. The Historic George Hotel

The Historic George Hotel

3.5 star property

Downtown Klamath Falls

8.6 out of 10, Excellent, (32 reviews)

8.6/10

Excellent

(32 reviews)

"It was clean, comfortable easy to get around the gathering coffee shop just down the street was awesome"

austen

The price is S$168

S$168

includes taxes & fees

10 Nov - 11 Nov

The Historic George Hotel

A treehouse with multiple levels connected by wooden walkways.

A wooden cabin structure with a view of a forested area.

A night sky with stars and the Milky Way over a park with trees and a building.

A wooden cabin with a porch, a picnic table, and a small garden area.

5. Out 'N' About Treehouse Treesort

Out 'N' About Treehouse Treesort

2.5 star property

Cave Junction

9.4 out of 10, Exceptional, (34 reviews)

9.4/10

Exceptional

(34 reviews)

"Nice unique place to stay. Kitchen setup is great with all utensils and facilities, good entertainments"

ravendran

The price is S$275

S$275

includes taxes & fees

10 Nov - 11 Nov

Out 'N' About Treehouse Treesort

A covered patio with a hammock chair, outdoor furniture, and a garden area with a stone pathway.

A modern kitchen with a dining area, a coat rack, and a clock on the wall.

A modern kitchen with a dishwasher, a refrigerator, and a microwave. There is a dining area with a table and chairs.

A bedroom with a bed, a television on a dresser, a door, and an air conditioning unit.

6. Basecamp GP Private Unit in Quiet Duplex

Basecamp GP Private Unit in Quiet Duplex

3.5 star property

Grants Pass

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Easy location to find, quiet neighborhood, comfy beds and perfect for my dogs. I would recommend people to stay there."

Chantelle

The price is S$225

S$225

includes taxes & fees

17 Nov - 18 Nov

Basecamp GP Private Unit in Quiet Duplex

A spacious kitchen with a central island, bar stools, and a fireplace.

A modern kitchen with a large island, white cabinetry, and a view of the city.

A spacious dining area with a long wooden table and cushioned chairs, a bookshelf, and a fireplace.

A cozy living room with a sofa, a woven hanging chair, a round pouf, and a large abstract painting.

7. Paschal Winery

Paschal Winery

4.5 star property

Talent

9.8 out of 10, Exceptional, (19 reviews)

9.8/10

Exceptional

(19 reviews)

"Stunning scenery, great wine and food. Friendly, helpful people on site and the hot tub is blissfully perfect ❤️"

Christine

The price is S$543

S$543

includes taxes & fees

10 Nov - 11 Nov

Paschal Winery

A deck with a fire pit, outdoor seating, and a view of the countryside.

A bed with a striped bedspread, a blanket, and an open book. There is a window with a view of trees and hills.

A spacious living room with a large sofa, a coffee table, and a view of the outdoors.

A modern bedroom with a large bed, bedside tables, and a view of the outdoors.

8. Grandview of Ashland

Grandview of Ashland

3.0 star property

Ashland

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Stunning views!! A+++ Experience!!"

Jose

The price is S$467

S$467

includes taxes & fees

10 Dec - 11 Dec

Grandview of Ashland

A covered outdoor seating area with chairs and tables, a fire pit, and a view of a lake.

A row of cabins with a picnic table and a covered seating area.

A compact kitchen with a dining table, wooden cabinets, a refrigerator, and a microwave.

A cabin with a 'Welcome' sign, a bench, and a covered area.

9. 'crater Lake' Williamson River Resort Cabin 1

'crater Lake' Williamson River Resort Cabin 1

3.0 star property

Chiloquin

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Clean, nice amenities, friendly proprietor, pleasant ground, smallish for two people."

Allan

The price is S$288

S$288

includes taxes & fees

17 Nov - 18 Nov

'crater Lake' Williamson River Resort Cabin 1

A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

A two-story house with a porch, a fenced yard, and a clear sky.

A living room with a fireplace, leather sofa, and a patterned rug.

A living room with a sofa, armchair, wooden bookshelves, a fireplace, and a patterned rug.

10. Savage Upon Siskiyou

Savage Upon Siskiyou

3.0 star property

Siskiyou-Hargadine Historic District

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Had an amazing stay, thank you!"

megan

The price is S$452

S$452

includes taxes & fees

10 Nov - 11 Nov

Savage Upon Siskiyou

A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

A single-story house with a covered porch, a small garden with rocks and a tree, and a mailbox.

A compact kitchen with white cabinets, a microwave, and a sink. There is a dining area with a wooden table and chairs, and a small seating area with a blue chair and a table.

A spacious living room with a wooden floor, a sofa, a dining table, and a kitchen area visible through an open doorway.

11. Hanna's House by WanderLodges

Hanna's House by WanderLodges

4.0 star property

Historic Railroad District

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!"

Robert

The price is S$229

S$229

includes taxes & fees

10 Nov - 11 Nov

Hanna's House by WanderLodges

A modern living room with a wooden dining table, a bench, and a fireplace.

A living room with a fireplace, two armchairs, a sofa, a coffee table, and a rug.

A single-story house with a green exterior, brick foundation, and a porch with wooden columns.

12. Redwoods Stopover by WanderLodges

Redwoods Stopover by WanderLodges

2.0 star property

Cave Junction

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Beautiful home. My truck didn’t fit in the garage but there’s a gate that I was able to park it behind. Support staff were super helpful."

Braden

The price is S$280

S$280

includes taxes & fees

11 Nov - 12 Nov

Redwoods Stopover by WanderLodges

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Boutique Hotels in Ashland
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Ashland Hotels
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Bly Hotels
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Private Holiday Homes in Bonanza
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B&B in Central Point
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Cottages in Central Point
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America's Best Inns Hotels in Central Point
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Central Point Hotels
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Aparthotels in Central Point
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Chiloquin Hotels
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City Center Medford Hotels
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Cabin Rentals in Crater Lake
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Condo Resorts in Crater Lake
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Hotels with connecting rooms in Crater Lake
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Hotels with Hot Tubs in Crater Lake
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Hotels near Crater Lake National Park
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Hotels with Spa in Shady Cove
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Visit Bly
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Central Point Holidays
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Visit Crater Lake
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Visit Eagle Point
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Visit Gold Hill
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Visit Terminal City
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Train Mountain Railroad Museum
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Umpqua National Forest
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Visit Wizard Island
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Apex Car Rentals Rental Cars in City Center Medford
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Avis Rental Cars in Southern Oregon
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Things to do in Medford
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Southern Oregon Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southern Oregon holiday rentals

1. Union Creek Resort

2. Crater Lake Resort

3. Rocky Point Resort

4. The Historic George Hotel

5. Out 'N' About Treehouse Treesort

6. Basecamp GP Private Unit in Quiet Duplex

7. Paschal Winery

8. Grandview of Ashland

9. 'crater Lake' Williamson River Resort Cabin 1

10. Savage Upon Siskiyou

11. Hanna's House by WanderLodges

12. Redwoods Stopover by WanderLodges

Find holiday rentals that suit your style

Explore a world of travel with Expedia