Farmstay vacation rentals in Jackson County

Find and book unique farmstay rentals on Airbnb

Top-rated farmstay rentals in Jackson County

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

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Guest favorite

Home in Prospect

4.96 out of 5 average rating, 192 reviews

Crater Lake "Meadow House" near south entrance.

One of closest to Crater Lake (28.9 miles), Rogue River, Lost Creek Lake, 3 waterfalls, +100 ranch acres of woodland trails. Upscale creature comforts; 2-story, 2500 sq. ft., fully-renovated historic ranch home: hardwood floors, fireplace, large kitchen, 2 bedrms w/2 private baths +an xtra small sleeping room, views of mtns & meadows are spectacular. Enjoy the ranch & wildlife relaxing on wrap-around deck. Perfect for couples, small getaways & sm families (kids over 10),or a work away. No pets

Guest favorite

Guesthouse in Talent

4.94 out of 5 average rating, 185 reviews

Zen Loft immersed in nature and close to town

Zenith Farm welcomes you to a touch of Tuscany in Southern Oregon. You’ll enjoy privacy and breathtaking views of the Rogue Valley in the well appointed two bedroom Barn Loft. Situated on a 5-acre estate 4 mi. from downtown Ashland and 10 mi. from Medford, you'll be surrounded by an abundance of fine food, great entertainment, incl. world-famous Shakespeare and Britt Festivals, nightlife, family-friendly and outdoor activities, day trips to destination wineries, redwoods, Crater Lake and beyond.

Guest favorite

Farm stay in Days Creek

4.92 out of 5 average rating, 113 reviews

Family Retreat-Entire Barn + Free Farm Breakfast

Private House 2 kitchens, fully stocked, 2 Full bathrooms , 4 Private bedrooms,Bonus Kids Loft with 2 Twins 2 kids futons There is a memory foam sofa bed in the family room on one side. This Duplex joins together via a Sliding Barn Door into over 3000 Sq Feet Of Grand Rustic Décor. A great room with 20’ ceilings for gathering after a long day of play. We are dog friendly with plenty room to roam. Enjoy 2 private creek side Decks with views of the farm. We are dog friendly but Do Not allow CATS

Guest favorite

Guesthouse in Medford

4.92 out of 5 average rating, 377 reviews

The Greenwood Villa w/wood fire hot tub

The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

Guest favorite

Cottage in Phoenix

4.9 out of 5 average rating, 381 reviews

The Pear Cottage Where city and country life meet

This is on a 42 acre family farm that dates back to 1910. Beautiful, quiet and very relaxing. We think you will love this completely renovated living space. With a private deck off each bedroom with lots of outdoor seating. Our home is just minutes away from Ashland Shakespeare and Jacksonville Britt Festivals. We are surrounded by the most breathtaking wineries, Skiing, Hiking the Pacific Crest Trail, Crater Lake and lots more. Enjoy looking out of the beautiful hay field and having coffee.

Guest favorite

Cottage in Jacksonville

4.91 out of 5 average rating, 196 reviews

Cottage on River Farm -Applegate Wine Trail

Recently repainted and deep cleaned, cottage on a 5-acre, Applegate River farm near vineyards. This is a cozy cottage on "Red Barn Farm.” Enjoy a mini farm-stay experience with goats & chickens along the Applegate Valley Wine Trail. Walk to Red Lily Vineyards! Enjoy the private firepit with complimentary s’mores kit or walk down to the river and breath. We are 15 minutes from the historic gold-rush town of Jacksonville, home of the Britt Summer Music Festival. Wine Country Farm Stay dot come.

Guest favorite

Cottage in Phoenix

4.99 out of 5 average rating, 424 reviews

Modern Getaway on Sunflower Farm

Stunning modern getaway on a flower farm with spectacular views. Nestled in the heart of the valley. 15 minutes from Ashland and Jacksonville. Home of Shakespeare and Britt Festivals. Over 6 wineries and a distillery within a 3 mile radius. Bright design with beautiful features. The many windows and French doors offer light in all directions with views of sunflowers, pear orchards and Roxy Ann Peak. One mile from the Greenway, a bike and pedestrian pathway linking Central Point to Ashland.

Guest favorite

Cottage in Central Point

4.96 out of 5 average rating, 113 reviews

Sweet Rose Cottage

This beautifully designed 1800 sq/ft cottage at Sweet Rose Farm offers rare seclusion and privacy located very close to historic Jacksonville. Bountiful views of agricultural land surrounds with pear orchards, fields, vineyards, ponds and of course the beautiful horses stabled at Sweet Rose Farm. The furnishings, beds and bedding are as expected at higher price points. Relax inside or out with a cup of coffee from the Jura espresso machine while taking in the many views from every window.

Guest favorite

Farm stay in Ashland

4.93 out of 5 average rating, 684 reviews

Kelly’s Farm 4 miles to Ashland

Nestled on the border of the Shakespeare hamlet of Ashland, Oregon, is Kelly’s farm. Only four miles away, come soak in the views. Kelly’s farm has horses, goats, chickens, gardens, fruit and nut trees with views of Mt. Ashland’s seven-thousand feet high profile in its front and bucolic rolling hills in its back. Bring your dog! You have access to a large fenced in yard right from your private entrance and deck. ***Unfortunately we are not set up for children under 4 or kitty cats. ***

Guest favorite

Cottage in Ashland

4.93 out of 5 average rating, 228 reviews

Weisinger Winery Vineyard Cottage

Our vineyard cottage is located at Weisinger Family Winery in Ashland, Oregon. Built c. 1920, our vineyard cottage was the original farmhouse on the property and was recently remodeled in order to encompass the amenities and comforts of home. The hot tub and BBQ on the deck overlook our Pinot Noir vineyard. The property has wonderful views and privacy. A complimentary bottle of wine, cheese, and crackers are awaiting your arrival along with a free tasting in our tasting room.

Guest favorite

Guest suite in Medford

4.97 out of 5 average rating, 143 reviews

Vineyard Views from 2 Bdrm Suite on the Farm

The guesthouse on our little farm overlooks the vineyard and the fields beyond. We are in the perfect spot to easily access many of the wonderful things Southern Oregon has to offer. Explore wineries, including our own, hiking trails, the Britt festival, and more! The guesthouse has lots of amenities, including an outdoor grill, kitchenette with fridge and hot plate, and full-size sleeper-sofa. Pack & play and other baby/child amenities are available upon request.

Guest favorite

Guesthouse in Ashland

4.95 out of 5 average rating, 111 reviews

Ashland Artist Country Retreat

Lovely light-filled, artistic, private, quiet, two-level studio apartment with full bath and kitchenette located on an organic farm in a beautiful country setting, just 3.6 miles to downtown Ashland and the Oregon Shakespeare Festival. Enjoy a private garden and views of the trees and mountains, as well as original art made by your host. We offer organic and upscale amenities and use only eco-friendly and healthy cleaners.