Pet-friendly holiday rentals in Jackson County

The Hygge Stay in the Heart of Southern Oregon

Pet friendly**Close to the I-5 interstate. Within walking distance to park! This guest house, is filled with natural light making it bright and inviting. Thoughtfully designed with guests in mind, you will have no trouble feeling comfortable with all the amenities you’ll need. *Fun fact**, the night stands in the main bedroom were made in the shop downstairs and designed by husband and I! *Airbnb is above working cabinet shop* Message me if you have any questions, I’ll respond within an hour!

Spa Like Stay at the Britt Bungalow in J’Ville

The Britt Bungalow is an Award Winning boutique style stay in the historical heart of Jacksonville Oregon created and designed by the owner and host. Enjoy a spa like private stay w/ 2 bed, 2 bath cottage with 17' ceilings, fresh flower’s throughout, #1 rated Dreamcloud mattress in Master, fireplaced open living room with an abundance of natural light throughout. You will want for nothing during your stay. Just 2 blocks to the trolly, all the best restaurants, boutiques, Britt Gardens, and more

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

Serene & Spacious E. Medford Studio with own W/D

Clean and spacious daylight lower level studio convenient to everything in Medford. Walkable to Starbucks and Providence Hospital and within 5 min drive to I-5, the airport, Asante RRMC and all major shopping/restaurants. There’s a separate private and fully lit entrance to the unit with no awkward shared spaces(!) and you’ll have use of a personal in-unit washer/dryer, countertop dishwasher, refrigerator, and an induction cooktop for meal prep. Ideal for traveling healthcare workers!

Countryman-Fox Carriage House

Considering the central location of this little gem, it is amazingly peaceful. To add to this charm, the cottage is fresh & bright with a lovely view across the valley. What a joy to walk across the street to the theater & dinner without parking issues. Besides being clean & safe, I like the king size bed, the fireplace, the choice of large tub or shower, the heated bathroom floor, and the little yard, the most. Charging is available for your electric cars in the upper parking area.

Studio Cottage near downtown Ashland - Queen Bed!

Take it easy at this unique and tranquil small studio cottage getaway. Our guest cabin is perfectly located minutes off the 5 freeway and just 3 miles from downtown Ashland's Shakespeare Festival, Plaza shops, beautiful Lithia Park and Restaurants. Venture to local lakes including Crater Lake, historic Jacksonville, and wineries in the picturesque Rogue Valley from our central location. Enjoy the privacy of our gated property with peaceful surroundings! Pets accepted with pet fee.

5 Star Luxury Southern Oregon Suite

Great little getaway on the outskirts of town. Away from the hustle and bustle of the city center, but minutes away from all the great places the Rogue Valley has to offer. This 800 sq foot apartment has been completely renovated to meet all the needs of travelers that are looking for an overnight stay or a long term place to land. This space offers updated heating and air, strong wi-fi, separate bedroom and working space. 2 smart TV's, designated parking, and a private entrance.

Cozy Jacksonville Cottage

This cozy, rustic one bedroom cottage (325 sq. ft.) is just a 15 min. walk from downtown Jacksonville (3/4 mile) and 30 min. from Ashland. It has private parking, on the property. The owner is happy w/ pets in the cottage, but needs to know in advance that a pet is coming (maximum 35lbs) too. There isn't a full kitchen but it has a kitchenette with sink, fridge, microwave, hot plate and coffee maker, so cooking basics won't be a problem. Relax in the outside patio in the summer.

Mindy’s Ashland Hideaway

Detached guest house offers a 5 minute drive to the I5 exit/Tesla Chargers & 10 mins to downtown Ashland. spacious, rural feel nestled by open pasture on a serene 1 acre property, this quiet getaway is great for a relaxing vacation, or a quick recharge! With enough parking for a trailer, boat, or other toys, this could be your spot to refresh on your road trip. Quick access to Oregon Shakespeare Festival , wineries, fishing, hiking, mountain biking, or Skiing in Southern Oregon!

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 from Ashland. 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.

Peach Street Super Suite

Welcome to our updated 1-bedroom short-term apartment in the heart of Medford, Oregon, designed to exceed your expectations and provide a more comfortable and affordable alternative to a hotel stay. As you step into our centrally located apartment, you'll immediately notice the modern and inviting atmosphere. The living room is tastefully furnished with a cozy sofa, a smart TV for your entertainment needs, and a dining area perfect for enjoying meals or working remotely.

Southern Oregon Gem (EV Charger)

Welcome to our charming little home in Medford, Oregon. a delightful haven designed for comfort, cleanliness, and efficiency. Nestled near the city center, this inviting space offers a perfect blend of coziness and functionality for a memorable stay. The thoughtful layout maximizes every inch of space, creating a welcoming atmosphere for solo travelers, couples, or small groups. The color palette is soothing, creating a serene ambiance that promotes relaxation.