Villa holiday rentals in Jackson County

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Top-rated villa rentals in Jackson County

Guests agree: These villas are highly rated for location, cleanliness and more.

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Villa in Applegate

4.7 out of 5 average rating, 10 reviews

Riverside Vineyard Estate

On over 800 ft of year-round flowing Applegate River frontage for trout, fishing, swimming, rafting, stand-up paddleboarding, kayaking, or just relaxing. Enjoy amazing mountain & river views from the expansive deck to chill by the fabulous river. Large club-style great room with plenty of natural light from large windows. Big screen cable TV, pool table, and yoga area. Entertainer's kitchen delight with large dining table for large gatherings. Proven venue for wedding events up to 150 guests!

Guest favourite

Villa in Ashland

4.92 out of 5 average rating, 24 reviews

Luxury Ashland Mountain Escape: Pool, Hot Tub

Live the Southern Oregon paradise life at the Jefferson Estate — a fabulously appointed home on 8 acres, perfect for group getaways or small gatherings. Take in views of Grizzly Peak while fishing in the small stocked pond, or soak in the seasonal outdoor pool or hot tub while enjoying the quiet of nature. Play games on the lawn, read by the living room fireplace, or try your hand at the billiards table. The kitchen is fully equipped to live out all your entertaining dreams, and a screened sun

Guest favourite

Villa in Ashland

4.98 out of 5 average rating, 43 reviews

The Gem & Cottage, Pool, Hot tub, Views

Magnificent Hilltop Getaway with Incredible Views (sleeps 14.) Come enjoy this oasis on the outskirts of the magical town of Ashland. This gorgeous home is perched above town on 3 acres offering some of the most epic mountain views and best sunsets in the valley. This special place pampers you with 5 bedrooms, 4 bathrooms, gas fireplace, hot tub, copper cold plunge, outdoor pool and multiple decks to take in the breathtaking views. Located 7 minutes from downtown Ashland.

Guest favourite

Villa in Ashland

5 out of 5 average rating, 6 reviews

The Gem~ Pool, Hot tub, Views

Magnificent Hilltop Getaway with Incredible Views (sleeps 10.) Come enjoy this oasis on the outskirts of the magical town of Ashland. This gorgeous home is perched above town on 3 acres offering some of the most epic mountain views and best sunsets in the valley. This special place pampers you with 4 bedrooms, 3 bathrooms, gas fireplace, hot tub, copper cold plunge, outdoor pool and multiple decks to take in the breathtaking views. Located 7 minutes from downtown Ashland.

Villa in Ashland

5 out of 5 average rating, 11 reviews

European Style County Estate

An exquisite European style country estate tucked in the picturesque Ashland countryside, Villa Paris Green is a hidden gem set within an 8-acre private estate. Located only 20 minutes from the town of Ashland and a convenient 40-minute drive from Medford Airport. Nestled amidst mountain ranges, Villa Paris Green is a perfect base for both relaxing and exploration.