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Holiday rentals in Southern Oregon

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Top-rated holiday rentals in Southern Oregon

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

Home in Ashland
Available! Spacious Historic Downtown Home!
Available October 17-January 29th and March through spring, 2023! This is a monthly rental. VERY LARGE (1,190 sq ft) historic home in downtown location in fun neighborhood, two blocks from Festival! Open floor plan, ONE level! Furnished. Wood floors. LARGE bedroom with bay window, QUEEN antique bed. Dining room with lovely lighting. Claw-foot bathtub with overhead shower. Office, game table, utility porch, laundry room. Includes all utilities, Wi-Fi, OFF STREET PARKING! No pets or smoking.
₹4,900 per night
SUPERHOST
Treehouse in Jacksonville
Tree Top Studio
Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.
₹14,117 per night
SUPERHOST
Cabin in La Pine
Deschutes A-Frame Cabin close to Bend
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.
₹17,069 per night
SUPERHOST

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Other great holiday rentals in Southern Oregon

Rental unit in Medford
Guest Suite w/ Kitchenette, private patio, parking
₹3,038 per night
Cabin in Ashland
Private Cottage Cabin Getway near Ashland Plaza!
₹6,534 per night
Guest house in Ashland
Cozy Cottage near Town!
₹4,574 per night
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Tiny home in Gold Beach
The Sunset
₹12,904 per night
SUPERHOST
Tiny home in Grants Pass
Pine Tree Cottage ·Tiny Cottage w/Firepit/Hottub/Outdoor tubs
₹8,004 per night
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Home in Gold Beach
Beach Bungalow - private beach and secluded hot tub
₹14,578 per night
SUPERHOST
Private room in Medford
Guestroom w/ private entrance + bath near downtown
₹4,084 per night
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Barn in Brookings
Barney's Barn
₹8,692 per night
SUPERHOST
Holiday home in Klamath Falls
NEW! The 'Easy A' Cabin in Rocky Point
₹8,307 per night
Guest suite in Medford
Private studio on serene urban farm
₹4,434 per night
Guest house in Ashland
Carter Lane Cottage
₹6,802 per night
SUPERHOST
Cottage in Roseburg
Grandma’s Cottage; Kitchen, W/D+Pets Okay
₹4,492 per night
SUPERHOST
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