Villa holiday rentals in Jackson County

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Top-rated villa rentals in Jackson County

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Villa in Applegate

4.63 out of 5 average rating, 8 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!

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Villa in Ashland

4.91 out of 5 average rating, 22 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

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Villa in Days Creek

Pachamama Farm Main Lodge Event Gathering space

Pachamama Farm Main Lodge is a secluded 110-acre retreat with 3 conjoined units—The Coop, Crow’s Nest & Lookout—each w/ private kitchens & baths. Dog-friendly (no cats). Families love trails, decks & animals. Enjoy complimentary breakfast: croissants, yogurt, fruit, oatmeal, coffee, tea & juice. Farm tours daily. Hike, stargaze, BBQ & unplug. Peaceful, scenic & unforgettable—perfect for retreats, reunions, families or anyone seeking authentic Oregon mountain life. Farm product for sale onsight

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Villa in Talent

5 out of 5 average rating, 14 reviews

Italian Villa with Hot Tub and Panoramic Views

Zenith Farm welcomes you to a touch of Tuscany in Oregon. Guests at the Villa will bask in the idyllic pastoral setting with breathtaking views of the valley. Situated on a 5-acre estate just 4 mi. from downtown Ashland and 10 mi. from Medford/Jacksonville, the area offers an abundance of fine food, entertainment (includ. the world-famous Shakespeare and Britt Festivals), nightlife, family-friendly and outdoor activities, wineries, day trips to redwoods, Crater Lake and a lot more.

Guest favourite

Villa in Medford

4.97 out of 5 average rating, 62 reviews

3 King Beds! BBQ, Game Room

This professionally designed spacious home sleeps up to 11 guests with six beds, 3,510 square feet, and multiple areas for entertaining. The kitchen is fully equipped for the cooks or entertainers in your party and the game room includes a 70" smart TV, wet bar, leather couches, foosball table, and arcade games. There's even a grand piano! In beautiful East Medford, you'll enjoy an easy stroll through a classic neighborhood. Close to downtown shopping, restaurants and wineries

Guest favourite

Villa in Ashland

4.97 out of 5 average rating, 39 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.

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.