Family-friendly vacation rentals in Ashland

Downtown Talent 2 BR bungalow

Sunny, Quiet, and clean in downtown Talent! Market, coffee shop, cafes, food trucks, Camelot Theater, library, playground, winery & shops in easy walking distance. Centrally located right between Ashland & Medford for discovering up and coming Talent while exploring the Rogue Valleys offerings: wine tasting, Oregon Shakespeare Festival, Britt Festival, historic Jacksonville, skiing or outdoor adventuring in mountains, or on rivers or lakes. We're dog friendly, but no dogs on furniture please.

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

Mexico Apartment at Wood Hamlet, by Downtown

The Wood Hamlet Mexico Apartment is a delightful space filled with color and culture. A short walk to town, 72-acre park & the theaters. Feel the welcoming warmth of the hand-crafted Mexican decor. Basement unit but with lots of windows and light. (4 beams at 6'1") Kitchen, with top of the line induction burner, fridge, microwave..., full bath, W/Dryer, work area... Wi-fi. Beautiful, garden with sitting areas & swimming pond. Parking. (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Historic Cottage close to plaza

Whimsical, cozy cottage located off quiet alley behind our main residence. Low-key, friendly neighborhood in the Skidmore Historic District. Front porch and back patio. Park your car and never get back in until it's time to leave. Street parking with a walk of about 250 feet to the cottage. Just 4 blocks from downtown. Full kitchen & laundry. A light-filled groovy hideaway. (Our wifi is good, but if you are doing zoom meetings, don't expect perfection.)

Artistic Airstream with panoramic 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.

Private Garden Cottage w Sauna in RR District

Located in the historic Railroad District, our cottage is walking distance from the Shakespeare theater and all the trimmings of downtown. Walk to an award winning coffee shop down the alley and two grocery stores and park. Set between the cottage and our house are beautiful vegetable and flower gardens. There is a great deck for morning coffee and secure bike storage available. Miles of mountain hiking trails are close by. This will be your new spot!

" sweet little garden studio "

Nice little shady deck with rocking chairs. Very quiet and safe little neighborhood. Great location. Eight minutes to downtown Ashland and 15 minutes to downtown Medford. Comfortable little Studio. Great for one or two busy guest. If bringing an animal please lmk beforehand of what kind and size. Im allowing one well behaved animal. Must not be left behind and clean up is a must. Thank you for understanding.

Railroad Cottage at Chozu Gardens

This charming cottage is located in the historic railroad district home to coffee houses, restaurants, and galleries. A 5 minute walk to downtown. It has a full kitchenette, fireplace like heater, orthopedic bed/ pillows and relaxing décor. Located one door down from Chozu Gardens (closed Mondays guests can take advantage of a 20% discount to soak and sauna in this serene setting.)

Ivy Cottage

Located in the heart of quaint Jacksonville, the Ivy Cottage is a cozy getaway. Just blocks from the main street and a short walk to Britt Music Festival makes this the perfect location for all visitors of the area. The Ivy Cottage was built in 1925 and was newly refurbished with love in 2018. Offering 2 bedrooms, 1 bath, and a memory foam sleeper sofa, can sleep up to 6 guest.