Farmstay vacation rentals in Jackson County

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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

Cottage in Grants Pass

4.96 out of 5 average rating, 196 reviews

Applegate Wine Country cottage!

Our "Lil Wanderer" cottage is located right in the middle of Southern Oregon wine country. We are right on the Applegate wine trail. You have your own private cottage to relax in as you take in the beautiful scenery of the surrounding landscape.With 7 wineries under 5 minutes away from the cottage, you’ll have plenty to explore right out your front door. Wooldridge, Walport,Troon, Schmidt, Blossom Barn, Rosellas & Solaro just to name a few. Downtown Grants Pass & Jacksonville are 30 minutes away

Aug 6 – 13

ﺩ.ﺇ544 per night

Guest favorite

Guesthouse in Medford

4.92 out of 5 average rating, 344 reviews

The Greenwood Villa

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

May 21 – 28

ﺩ.ﺇ626 per night

Guest favorite

Farm stay in Ashland

4.94 out of 5 average rating, 595 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. ***

Aug 12 – 19

ﺩ.ﺇ777 per night

Guest favorite

Cottage in Ashland

4.99 out of 5 average rating, 143 reviews

The Red Dragon House

Just a few minutes outside of Ashland, this unique and spacious property will put you in a rural setting with excellent views of the surrounding hills of the Rogue Valley. Located on 5.2 acres, with two security gates that are, remnants of a previous cannabis operation, the property affords ample privacy, and is invisible from the street, providing a perfect getaway for those that seek it. We are adjacent to I-5, so if road noise is an issue, this property may not be right for you.

Feb 7 – 14

ﺩ.ﺇ723 per night

Guest favorite

Cottage in Ashland

4.92 out of 5 average rating, 213 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.

Mar 18 – 25

ﺩ.ﺇ965 per night

Guest favorite

Ranch in Prospect

4.97 out of 5 average rating, 597 reviews

Crater Lake "Bunkhouse" on 100 acre ranch & trails

The private Ranch "BunkHouse" sits on a meadow near the horse paddocks & barn w/ views of valley, mountains, & access to gorgeous woodsy hiking trails. The "BunkHouse" retains the rustic charm of the original Bunkhouse but inside it enjoys new comfort, style & amenities! It's an up-dated large (20X40) open studio/bedrm w/ kitchenette & private bath (clawfoot shower/tub). A king-sized bed & extra twin bed if you have a 3rd traveling w/you, all in one room. Also, TV and WiFi

Oct 23 – 30

ﺩ.ﺇ541 per night

Guest favorite

Guest suite in Medford

4.96 out of 5 average rating, 126 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! This is a new space with 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.

Sep 14 – 21

ﺩ.ﺇ559 per night

Guest favorite

Farm stay in Days Creek

4.91 out of 5 average rating, 254 reviews

Ranch House #2 +Farm Breakfast Included

Spread out in 1500 Sq. Feet Of Grand Rustic Décor! Located in the original barn on the property, Our Charming Rustic Ranch House is part of a converted barn duplex. Featuring a fully stocked kitchen, full bathroom, 2 bedrooms(1 bedroom is spacious with a queen bed and chair. 1 bedroom has a Queen & Bunk Twin), Kids Loft & Game Room has 2 Twins and a great room with 20’ ceilings for gathering up after a long day of play. We are dog friendly but Do Not allow CATS

Nov 14 – 21

ﺩ.ﺇ533 per night

Guest favorite

Camper/RV in Talent

4.94 out of 5 average rating, 291 reviews

Peaceful, artistic Airstream with amazing views

This beautifully rebuilt Airstream, makes for the perfect cozy getaway. Perched on its own terrace on a 5+ acre Italian style estate you'll be surrounded by spectacular views, an abundance of fine food, entertainment (including the world famous Shakespeare and Britt Festivals), nightlife, endless family-friendly and outdoor activities, day trips to destination wineries, redwoods and Crater Lake. 4 mi. from downtown Ashland and 13 mi. from Medford airport.

May 13 – 20

ﺩ.ﺇ276 per night

Guest favorite

Guesthouse in Jacksonville

4.97 out of 5 average rating, 134 reviews

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***

Feb 25 – Mar 4

ﺩ.ﺇ399 per night

Guest favorite

Guesthouse in Medford

4.95 out of 5 average rating, 152 reviews

Cottage with jetted tub and fine linens

Nestled in rich farmland just north of historic Jacksonville and Britt Gardens, this cottage is just minutes away from everything the Rogue Valley has to offer. Whether you are visiting to taste award-winning wines, craft-brewed beers, experience outdoor concerts at the Britt - or all of the above - you will find you are right in the middle of the action.

Feb 12 – 19

ﺩ.ﺇ400 per night

Guest favorite

Cottage in Central Point

4.9 out of 5 average rating, 143 reviews

Farm Cottage 1/2 Mile Outside Jacksonville

Private cottage with fenced yard. 1/2 mile to historic Jacksonville and the famous Britt Festival. Noted local winery Rellik is one property away and we are in the heart of the Rogue Valley wine country. Pool available in the summer and meeting our farm animals is available with advanced notice. Our place is designed to help you create lasting memories!

Jul 9 – 16

ﺩ.ﺇ346 per night