Family-friendly holiday rentals in Ashland

Victorian Garden Carriage House

You will wake in the trees, to the soft prospects of the forested Siskiyou mountains to the west. You'll discover enchanting views at every window, from city streets to a quiet English garden and pond. You are only a few steps from Ashland Plaza, yet the retreat-like environment we offer to all our guests requires that no incense, smoking, vaping or pets are allowed in the Carriage House. The City of Ashland has authorized the Carriage House. Our City Planning Action Number is PA-2013-01701.

Tiny House in the country

This is a tiny house that's located in the countryside. There's a double matress on the loft that's serves as the sleeping area, also a sofa bed in the living room. Since it's a tiny house we don't have a formal kitchen. We do have have a microwave, coffee maker and a fridge. We don’t serve breakfast. We live beside this house so you can easily contact us if you any concern. Smoking and pets are not allowed. We only have WiFi extender so sometimes you can’t get a signal from the tiny house

Ashland Haus Retreat - 1 block from downtown!

This beautiful 10 foot ceiling home is ideal for your stay in Ashland. Our classic two bedroom 1900s home has many new renovations (floors, appliances, furniture-- all done in August 2017). Enjoy a short walk to great cafes, restaurants and breweries! We are about an 8 minute walk to the Shakespeare Festival. One bedroom has a queen bed, the other has a king bed that can be made into two singles. The sleeper sofa is in living room. The bedrooms share a Jack&Jill bathroom. PA # PA-2017-01160

The Cedar Cottage - creekside studio

This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

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.

C Street Station Cottage

Light, bright and simply gorgeous, this charming studio is just a ten minute walk from the Festival downtown and is the perfect place to enjoy Southern Oregon. Tucked into a quiet neighborhood in the Historic Railroad District. The space includes a luxurious king bed. bathroom with shower and tub, fireplace, flat screen Smart TV, washer/dryer, and kitchenette. Large private parking space right by the door and the covered patio includes a dining area and barbeque. Designer inspired.

Secluded mountain retreat, 10m. to Ashland, by PCT

Beautiful hand built log house nestled in the Cascade mountains of Southern Oregon. 15 minutes to Ashland, 20 minutes to Mt. Ashland Ski Area, and a three minute walk to Pacific Crest Trail. This home is a cozy, quiet getaway: surrounded by a 38 acre old forest w/ endless mountains and trails at your doorstep. Features include glassed in sun room (sleep under the stars), fully equipped kitchen, large covered deck, seasonal wood-fired sauna, swimming pond and walking trails.

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.

Summer’s Night Cottage 8 minute walk to Downtown

Clean and comfortable cottage perfect for a getaway. Short distance to downtown Ashland, Lithia Park, Oregon Shakespeare Festival, and more. Great outdoor space. Relax in our clean 1 bedroom cottage with a newer queen bed, high thread count sheets, and convertible full size sofa, sleeping area. Walk to one of the many restaurants & bars or fix a simple meal with provided hot plate and kitchen basics.

Creekside Retreat Close to Town

You will be a 10 minute drive from Downtown Ashland and feel like you are out in the country. The home sits on 8 private acres and has river frontage and a beach on the year round Emigrant Creek. There are beautiful views in all directions of mountains, trees and wildlife. The home is a two story residential barn built in 2012 and remodeled in 2022 (the main living quarters is upstairs).

Clean, Stylish Apt w/kitchen. block from Downtown

92½ Church Street. A private apartment with a large bedroom, full kitchen, bath with shower. Vintage styling with loads of special touches, ONE BLOCK from downtown. All the comfort of home and so close to the action. Large yard. Permitted. (Ashland City Permit: 15-237). 2020 Update: We have adopted the recommended Covid-19 Cleaning Guidelines.