Farmstay vacation rentals in Jackson County

The Green Arrow Cabinette

Tucked in a serene nook of the breathtaking Colestin Valley, this tiny house was built with reclaimed and repurposed materials from a historic local housing district. A pair of outdoor, porcelain bathtubs and seasonal fire pit complete the unique, private setting—primed for travelers wanting to get off the beaten path, but within five minutes of I-5, also a convenient stop for road trippers looking to break up a long drive. And we're pet friendly! See House Rules for details on pet and tub fees.

Sunnybrook Guest Cabin

Visit Sunnybrook, our working ranch. The cabin features a queen sized bed as well as a twin bed in the loft. A cot and crib are available upon request. There is a full kitchen and comfortable bathroom. Wifi is available along with a Smart TV. Enjoy miles of trails on the property with access to hundreds more miles of BLM trails from the property. Bring horses, ATV’s and your hiking shoes. Take a swim or just relax by the creek. Apple, pear, plum and blackberry picking is available seasonally.

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

Creekside cabin on 100 acres

Complementary eggs, sausage, croissants, yogurt, oatmeal, fruit, coffee, tea & juice. 2BR, 1BA ranch house w/ kitchenette, 11 cu ft fridge, 4-burner stovetop, toaster oven, & laundry. Sleeps 6 family-style or 2 unrelated adults. Fast Wi-Fi, landline, 400-thread-count linens, fuzzy throws, peaceful vibes. 🐶 Dog-friendly 🚫 No cats 🚭 No smoking indoors. Covered carport parking. Clean, scenic, restful, ideal for nature lovers. Explore creeks, stargaze, or just unplug and reconnect with nature.

Shakespeare Peaceful Getaway. Vast panoramic view.

Welcome to our little Italy in the Rogue Valley. Perched on a scenic ridge, the Barn offers serene privacy, sweeping views, and countryside charm just minutes from Ashland and Medford. This stylish retreat is perfect for nature lovers and culture seekers alike. Nearby enjoy world-class wineries and eateries, internationally acclaimed Oregon Shakespeare (OSF) and Britt Festivals, family friendly events, hiking, biking, fishing, Crater Lake NP, Redwoods NP.The possibilities are endless! Book Now!

Enchanted Conestoga wagon on the Applegate River

Reconnect with nature in the breathtaking Applegate Valley while enjoying the comfort of our cozy covered wagon. Take a step back in time and create memories as our ancestors did on the Oregon trail in covered wagons. Escape the hustle and bustle of everyday life & unwind in harmony with nature on the Applegate River. Enjoy the many nature trails that meander throughout the 12 acres on our farm. Say hello to all of the cute furry animals grazing on our pasture. Your adventure awaits!!

Wine Country Farm Stay Near Ashland

Stunning romantic wine getaway on a flower farm with spectacular views. Farm stay offers the perfect base for exploring the Rogue Valley wine trail, 15 minutes to over 20 Jacksonville and Ashland wineries in the heart of the valley. Cozy private deck offers a perfect spot to relax and enjoy wine with views of mountains, pastures, and fields. Home of the Oregon Shakespeare and Britt Festivals. One mile from the Greenway, a bike and pedestrian pathway. Enjoy a beautiful ride to local wineries.

Cabin Serenity at Applegate Winery

Escape to your own cozy cabin, tucked away in a private wooded forest on a stunning vineyard & winery. Perfect for a quiet & peaceful getaway! Wake up to forest views from your king bed or unwind with a glass of wine on one of two private decks. Located at Walport Family Cellars in the heart of Applegate wine country, with 18+ wineries nearby—many within walking distance! For guests over 21, enjoy honorary wine club perks, including complimentary flights and purchase discounts!

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.

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.

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.

Valhalla Cabin, King Bed, Hiking, close to Britt

Tranquility & hiking. 128 AC of wooded acreage to hike on. The flowers bloom in the spring! Come and see! We are located about 20 min from The Britt in Jacksonville. Check out their venue and list of performers! ***This is a NO SMOKING IN OR OUT of the unit/property, This cabin is NOT suitable for children, No animals allowed EXCEPT for service dogs. When there is snow, 4-wheel vehicles are advised***