House vacation rentals in Ashland

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

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

Cute 2 bdr house near downtown (pet friendly)

Cute 2 bdr, 1.5 ba house only a few blocks away from beautiful downtown Ashland (3 min drive, 10 min walk). Amenities include: - Fenced in private backyard - Well stocked kitchen - Central Air - Dining set seats 4-6 - Jack and Jill bathroom and 1 half bath - Patio, bbq - Washer & Dryer - TV with Apple TV - Wifi - 2 parking spaces - There is no dishwasher Note that bears sometimes come around the neighborhood at night looking for food and get into the trash bins. They are not aggressive.

Cedar Mountain Suite A -Home Theater, Gamer Ready!

Welcome to The Entertainment House! This 2-bedroom, 2-bathroom home offers the ultimate theater experience with its impressive 86" TV and Surround Sound System. Located just a 5-minute walk from JetBoat Excursions, Riverside Park, and the Historic Downtown District, complete with bars, restaurants, and antique shops. Despite its proximity to these lively attractions, this location provides a peaceful and private environment, making it feel like you're perched high on a mountaintop in Aspen!

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!

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.

Holly House: a Pet-friendly Garden Eco-Cottage

Adorable, light-filled, freshly-renovated 2-bedroom, 1.5-bath, 1940’s cottage-style home. Beautifully decorated with modern finishes and mid-century charm to create a timeless and elevated style. Private sitting and eating area on back deck surrounded by a beautiful garden of grass and flowers and two large shade trees. Easy walk to downtown Medford, restaurants, food trucks, and shopping. Easy drive to hiking trails, Rogue River, wineries, and wilderness adventures.

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.

Charming house two blocks from downtown Ashland

The Serendipity House is a comfortably stylish escape in the heart of Ashland. Our newly remodeled home has all the comforts you will need. Cozy beds for sleeping late, a full kitchen with a complimentary coffee bar, a living room for socializing with family and friends, and all the privacy of having the entire property to yourselves. Restaurants, shopping, and theater begin two blocks away. This is the perfect house for your unforgettable Ashland experience.

Swank House in Downtown Ashland

Dip into an Ashland vacation experience unlike any other. Stroll to your morning coffee or evening theater show from our newly renovated Main St home. Indoors, breathe easy with soaring vaulted ceilings and luxuries like the soaking tub and fully equipped kitchen. Outside, spend time with your feet up on the private outdoor patio. Our house is ideal for couples or families seeking extra space and privacy. A Swank House property. (#18-243)

Craftsman cottage built in 2019

One mile off interstate. This beautiful craftsman airbnb was built in 2019. and the attention to detail shows. Entire private house, large yard, washer/dryer, full kitchen, tiled shower, and upstairs with additional living space and bedroom. Close to Ashland, Jacksonville and Medford. Walking distance to the Phoodery, Clyde’s corner, and mini market. Space is not suitable for toddlers or elderly due to steep stairs leading to bedrooms.

Coyote Moon

Beautiful 1360 square foot home on 2 acres. Modern, shed roof design with great windows and view of Grizzly Peak. Quiet and peaceful but only 1.8 miles from the heart of downtown Ashland. Deck with propane fire table. Kitchen with quartz countertops and island. Perfect for a romantic couples getaway and also great for those visiting Ashland for the Oregon Shakespeare Festival. Wireless internet and Netflix and internet TV.