Family-friendly vacation rentals in Ashland

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Top-rated family-friendly rentals in Ashland

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Guest favorite

Guesthouse in Medford

4.92 out of 5 average rating, 370 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

Guest favorite

Guesthouse in Central Point

4.97 out of 5 average rating, 924 reviews

The West Wing Guest House

Located next to the main home, this detached guest house has a separate driveway/parking & hosts kitchen/living downstairs, with bedroom & bathroom upstairs. We are located 5 miles from Jacksonville, home of the Britt Festival & the best local wineries. About 20 minutes south is the town of Ashland, well known for the Shakespeare Festival. Downtown Central Point is just a mile away, where you will find the renowned Rogue Creamery. The house is also only 10 minutes from the Rogue Valley Airport.

Guest favorite

Home in Ashland

4.91 out of 5 average rating, 222 reviews

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

Guest favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 558 reviews

Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

Guest favorite

Camper/RV in Ashland

4.89 out of 5 average rating, 969 reviews

Cozy camping close to town

The 1973 Kit Companion is a 15-foot trailer converted to maximize space and guest experience. Featuring a water dispenser, hot water kettle, lending library, and games; this adorable camper is supremely functional and gives guests a unique and comfortable space. The “Kit” is small, private, and located conveniently close to Ashland's picturesque downtown and Interstate 5. Guests who stay in trailer have access to the shared bathroom and shower in the house.

Guest favorite

Guesthouse in Central Point

4.94 out of 5 average rating, 755 reviews

BEE WELL Organic Spa Garden Studio w/ Hot Tub

This detached 420 sf apartment is perfect for 1-2 guests. Light-filled studio (from two solar tubes) on over 1/3 acre of flowers and fruit trees, three blocks from downtown, and craft foods and wine. Very close and easy access from the highway. Jacksonville is 6 miles, and the Ashland plaza is 17 miles. Southern OR is filled with playhouses, delicious wine, yummy local restaurants, scenic rivers, and miles of wilderness. Come enjoy! We celebrate diversity!

Guest favorite

Camper/RV in Talent

4.94 out of 5 average rating, 309 reviews

Peaceful 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.

Guest favorite

Guesthouse in Ashland

4.89 out of 5 average rating, 379 reviews

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!

Guest favorite

Bungalow in Ashland

4.99 out of 5 average rating, 100 reviews

Penthouse Suite, easy walk to downtown.

The Penthouse Suite is the full top floor of the 2 story apartment building, that affords lovely views, and has been completely rebuilt in 2017! New kitchen and appliances, gas fireplace, & in house laundry. It has 3 bedrooms with 1 king, 2 queen, 1 full, & Q futon. It has 2.5 baths. Enjoy huge, partially covered deck, and gas grill. Downtown is 10/15 minute walk away. The local taxes are included in the price, account ID 527. Pets on approval.

Guest favorite

Cottage in Talent

4.76 out of 5 average rating, 428 reviews

" 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.

Guest favorite

Rental unit in Grants Pass

4.95 out of 5 average rating, 841 reviews

Peace on the Rogue river Studio

Beautiful park like setting on the Rogue river with a jacuzzi, swim spa two decks, fishing, yard games, hammock, barbecues, bicycles, kitchenette has Keurig With pods,a toaster oven, crock pot, small George Forman a portable two burner cook top , small skillet, one pot and most utensils to provide a meal. Minutes from Grants Pass, shopping, restaurants, and winery's.

Superhost

Guesthouse in Ashland

4.86 out of 5 average rating, 138 reviews

ABBOTT'S COTTAGES- Egret

A cozy hideaway for two tucked into a private corner, the Egret is a perfect place to come home to after enjoying a night at theatre or a walk in the park. Spanish tiles and hand forged iron accents add to the ambiance of this special studio cottage. There are other cottages on the property if you are with a group looking for more than one house. Just let us know!